Hydrogen bond: Difference between revisions

Latest revision as of 21:54, 26 May 2026

File:3D model hydrogen bonds in water.svg

Model of hydrogen bonds (1) between molecules of water

AFM image of naphthalenetetracarboxylic diimide molecules on silver-terminated silicon, interacting via hydrogen bonding, taken at 77 K.^[1] ("Hydrogen bonds" in the top image are exaggerated by artifacts of the imaging technique.^[2]^[3]^[4])

In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, covalently bonded to a more electronegative donor atom or group (Dn), interacts with another electronegative atom bearing a lone pair of electrons—the hydrogen bond acceptor (Ac). Unlike simple dipole–dipole interactions, hydrogen bonding arises from charge transfer (nB → σ*AH), orbital interactions, and quantum mechanical delocalization, making it a resonance-assisted interaction rather than a mere electrostatic attraction.^[5]

The general notation for hydrogen bonding is Dn−H···Ac, where the solid line represents a polar covalent bond, and the three dots indicate the hydrogen bond.^[6] Hydrogen bond donors have a protic hydrogen attached to an electronegative atom such as nitrogen (N), oxygen (O), and fluorine (F). Hydrogen bond acceptors have a lone pair of electrons, such as amines, carboxylates, and water.

The term "hydrogen bond" is generally used for well-defined, localized interactions with significant charge transfer and orbital overlap, such as those in DNA base pairing or ice. In contrast, "hydrogen-bonding interactions" is a broader term used when the interaction is weaker, more dynamic, or delocalized, such as in liquid water, supramolecular assemblies (e.g.: lipid membranes, protein-protein interactions), or weak C-H···O interactions. This distinction is particularly relevant in structural biology, materials science, and computational chemistry, where hydrogen bonding spans a continuum from weak van der Waals-like interactions to nearly covalent bonding.^[5]

Hydrogen bonding can occur between separate molecules (intermolecular) or within different parts of the same molecule (intramolecular).^[7]^[8]^[9]^[10] Its strength varies considerably, depending on geometry, environment, and the donor-acceptor pair, typically ranging from 4.2 to 167.4 kJ/mol (1 to 40 kcal/mol).^[11] This places hydrogen bonds stronger than van der Waals interactions but generally weaker than covalent or ionic bonds.

Hydrogen bonding plays a fundamental role in chemistry, biology, and materials science. It is responsible for the anomalously high boiling point of water, the stabilization of protein and nucleic acid structures, and key properties of materials like paper, wool, and hydrogels. In biological systems, hydrogen bonds mediate molecular recognition, enzyme catalysis, and DNA replication, while in materials science, they contribute to self-assembly, adhesion, and supramolecular organization.

Bonding

File:Hydrogen Bond Quadruple AngewChemIntEd 1998 v37 p75.jpg

An example of intermolecular hydrogen bonding in a self-assembled dimer complex.^[12] The hydrogen bonds are represented by dotted lines.

File:Acetylacetone tautomerism.svg

Intramolecular hydrogen bonding in acetylacetone helps stabilize the enol tautomer.

Definitions and general characteristics

In a hydrogen bond, the electronegative atom not covalently attached to the hydrogen is named the proton acceptor, whereas the one covalently bound to the hydrogen is named the proton donor. This nomenclature is recommended by the IUPAC.^[6] The hydrogen of the donor is protic and therefore can act as a Lewis acid and the acceptor is the Lewis base. Hydrogen bonds are represented as H···Y system, where the dots represent the hydrogen bond. Liquids that display hydrogen bonding (such as water) are called associated liquids.^{[citation needed]}

File:H-donor-acceptor.svg

Examples of hydrogen bond donating (donors) and hydrogen bond accepting groups (acceptors)

File:Acetic Acid Hydrogenbridge V.1.svg

Cyclic dimer of acetic acid; dashed green lines represent hydrogen bonds

Hydrogen bonds arise from a combination of electrostatics (multipole-multipole and multipole-induced multipole interactions), covalency (charge transfer by orbital overlap), and dispersion (London forces).^[6]

In weaker hydrogen bonds,^[13] hydrogen atoms tend to bond to elements such as sulfur (S) or chlorine (Cl); even carbon (C) can serve as a donor, particularly when the carbon or one of its neighbors is electronegative (e.g., in chloroform, aldehydes and terminal acetylenes).^[14]^[15] Gradually, it was recognized that there are many examples of weaker hydrogen bonding involving donor other than N, O, or F and/or acceptor Ac with electronegativity approaching that of hydrogen (rather than being much more electronegative). Although weak (about 4.2 kJ/mol (1 kcal/mol)), "non-traditional" hydrogen bonding interactions are ubiquitous and influence structures of many kinds of materials.^{[citation needed]}

The definition of hydrogen bonding has gradually broadened over time to include these weaker attractive interactions. In 2011, an IUPAC Task Group recommended a modern evidence-based definition of hydrogen bonding, which was published in the IUPAC journal Pure and Applied Chemistry. This definition specifies:

The hydrogen bond is an attractive interaction between a hydrogen atom from a molecule or a molecular fragment X−H in which X is more electronegative than H, and an atom or a group of atoms in the same or another molecule, in which there is evidence of bond formation.^[16]

Bond strength

Hydrogen bonds can vary in strength from weak (1–2 kJ/mol) to strong (161.5 kJ/mol in the bifluoride ion, HF₂^-).^[17]^[18] Typical enthalpies in vapor include:^[19]

F−H···F⁻ (161.5 kJ/mol (38.6 kcal/mol)), illustrated uniquely by HF₂^-
O−H···N (29 kJ/mol (6.9 kcal/mol)), illustrated water-ammonia
O−H···O (21 kJ/mol (5.0 kcal/mol)), illustrated water-water, alcohol-alcohol
N−H···N (13 kJ/mol (3.1 kcal/mol)), illustrated by ammonia-ammonia
N−H···O (8 kJ/mol (1.9 kcal/mol)), illustrated water-amide
OH+3···OH₂ (18 kJ/mol (4.3 kcal/mol))^[20]

The strength of intermolecular hydrogen bonds is most often evaluated by measurements of equilibria between molecules containing donor and/or acceptor units, most often in solution.^[21] The strength of intramolecular hydrogen bonds can be studied with equilibria between conformers with and without hydrogen bonds. The most important method for the identification of hydrogen bonds also in complicated molecules is crystallography, sometimes also NMR-spectroscopy. Structural details, in particular distances between donor and acceptor which are smaller than the sum of the van der Waals radii can be taken as indication of the hydrogen bond strength. One scheme gives the following somewhat arbitrary classification: those that are 63 to 167 kJ/mol (15 to 40 kcal/mol), 21 to 63 kJ/mol (5 to 15 kcal/mol), and 0 to 21 kJ/mol (0 to 5 kcal/mol) are considered strong, moderate, and weak, respectively.^[18]

Hydrogen bonds involving C−H bonds are both very rare and weak.^[22]

Resonance assisted hydrogen bond

The resonance assisted hydrogen bond (commonly abbreviated as RAHB) is a strong type of hydrogen bond. It is characterized by the π-delocalization that involves the hydrogen atom and cannot be properly described by the electrostatic model alone. This description of the hydrogen bond has been proposed to describe unusually short distances generally observed between O=C−OH··· or ···O=C−C=C−OH.^[23]

Structural details

The X−H distance is typically ≈110 pm, whereas the H···Y distance is ≈160 to 200 pm. The typical length of a hydrogen bond in water is 197 pm. The ideal bond angle depends on the nature of the hydrogen bond donor. The following hydrogen bond angles between a hydrofluoric acid donor and various acceptors have been determined experimentally:^[24]

Acceptor···donor	VSEPR geometry	Angle
HCN···HF	C≡N···H angle: linear	180°
H₂CO···HF	C=O···H angle: trigonal planar	120°
H₂O···HF	H-O···H angle: pyramidal	46°
H₂S···HF	H-S···H angle: pyramidal	89°
SO₂···HF	S=O···H angle: trigonal	145°

Spectroscopy

Strong hydrogen bonds are revealed by downfield shifts in the ¹H NMR spectrum. For example, the acidic proton in the enol tautomer of acetylacetone appears at Template:Tmath 15.5, which is about 10 ppm downfield of a conventional alcohol.^[25]

In the IR spectrum, hydrogen bonding shifts the X−H stretching frequency to lower energy (i.e. the vibration frequency decreases). This shift reflects a weakening of the X−H bond. Certain hydrogen bonds - improper hydrogen bonds - show a blue shift of the X−H stretching frequency and a decrease in the bond length.^[26] H-bonds can also be measured by IR vibrational mode shifts of the acceptor. The amide I mode of backbone carbonyls in α-helices shifts to lower frequencies when they form H-bonds with side-chain hydroxyl groups.^[27] The dynamics of hydrogen bond structures in water can be probed by this OH stretching vibration.^[28] In the hydrogen bonding network in protic organic ionic plastic crystals (POIPCs), which are a type of phase change material exhibiting solid-solid phase transitions prior to melting, variable-temperature infrared spectroscopy can reveal the temperature dependence of hydrogen bonds and the dynamics of both the anions and the cations.^[29] The sudden weakening of hydrogen bonds during the solid-solid phase transition seems to be coupled with the onset of orientational or rotational disorder of the ions.^[29]

Theoretical considerations

Hydrogen bonding is of persistent theoretical interest.^[30] According to a modern description O:H−O integrates both the intermolecular O:H lone pair ":" nonbond and the intramolecular H−O polar-covalent bond associated with O−O repulsive coupling.^[31]

Quantum chemical calculations of the relevant interresidue potential constants (compliance constants) revealed^[how?] large differences between individual H bonds of the same type. For example, the central interresidue N−H···N hydrogen bond between guanine and cytosine is much stronger in comparison to the N−H···N bond between the adenine-thymine pair.^[32]

Theoretically, the bond strength of the hydrogen bonds can be assessed using NCI index, non-covalent interactions index, which allows a visualization of these non-covalent interactions, as its name indicates, using the electron density of the system.^{[citation needed]}

Interpretations of the anisotropies in the Compton profile of ordinary ice claim that the hydrogen bond is partly covalent.^[33] However, this interpretation was challenged ^[34] and subsequently clarified.^[35]

Most generally, the hydrogen bond can be viewed as a metric-dependent electrostatic scalar field between two or more intermolecular bonds. This is slightly different from the intramolecular bound states of, for example, covalent or ionic bonds. However, hydrogen bonding is generally still a bound state phenomenon, since the interaction energy has a net negative sum. The initial theory of hydrogen bonding proposed by Linus Pauling suggested that the hydrogen bonds had a partial covalent nature. This interpretation remained controversial until NMR techniques demonstrated information transfer between hydrogen-bonded nuclei, a feat that would only be possible if the hydrogen bond contained some covalent character.^[36]

History

The concept of hydrogen bonding once was challenging.^[37] Linus Pauling credits T. S. Moore and T. F. Winmill with the first mention of the hydrogen bond, in 1912.^[38]^[39] Moore and Winmill used the hydrogen bond to account for the fact that trimethylammonium hydroxide is a weaker base than tetramethylammonium hydroxide. The description of hydrogen bonding in its better-known setting, water, came some years later, in 1920, from Latimer and Rodebush.^[40] In that paper, Latimer and Rodebush cited the work of a fellow scientist at their laboratory, Maurice Loyal Huggins, saying, "Mr. Huggins of this laboratory in some work as yet unpublished, has used the idea of a hydrogen kernel held between two atoms as a theory in regard to certain organic compounds."

Hydrogen bonds in small molecules

File:Hex ice.GIF

Crystal structure of hexagonal ice. Gray dashed lines indicate hydrogen bonds

File:NIMGLO12.png

Structure of nickel bis(dimethylglyoximate), which features two linear hydrogen-bonds.

Water

An ubiquitous example of a hydrogen bond is found between water molecules. In a discrete water molecule, there are two hydrogen atoms and one oxygen atom. The simplest case is a pair of water molecules with one hydrogen bond between them, which is called the water dimer and is often used as a model system. When more molecules are present, as is the case with liquid water, more bonds are possible because the oxygen of one water molecule has two lone pairs of electrons, each of which can form a hydrogen bond with a hydrogen on another water molecule. This can repeat such that every water molecule is H-bonded with up to four other molecules, as shown in the figure (two through its two lone pairs, and two through its two hydrogen atoms). Hydrogen bonding strongly affects the crystal structure of ice, helping to create an open hexagonal lattice. The density of ice is less than the density of water at the same temperature; thus, the solid phase of water floats on the liquid, unlike most other substances.^{[citation needed]}

Liquid water's high boiling point is due to the high number of hydrogen bonds each molecule can form, relative to its low molecular mass. Owing to the difficulty of breaking these bonds, water has a very high boiling point, melting point, and viscosity compared to otherwise similar liquids not conjoined by hydrogen bonds. Water is unique because its oxygen atom has two lone pairs and two hydrogen atoms, meaning that the total number of bonds of a water molecule is up to four.^[41]

The number of hydrogen bonds formed by a molecule of liquid water fluctuates with time and temperature.^[42] From TIP4P liquid water simulations at 25 °C, it was estimated that each water molecule participates in an average of 3.59 hydrogen bonds. At 100 °C, this number decreases to 3.24 due to the increased molecular motion and decreased density, while at 0 °C, the average number of hydrogen bonds increases to 3.69.^[42] Another study found a much smaller number of hydrogen bonds: 2.357 at 25 °C.^[43] Defining and counting the hydrogen bonds is not straightforward however.

Because water may form hydrogen bonds with solute proton donors and acceptors, it may competitively inhibit the formation of solute intermolecular or intramolecular hydrogen bonds. Consequently, hydrogen bonds between or within solute molecules dissolved in water are almost always unfavorable relative to hydrogen bonds between water and the donors and acceptors for hydrogen bonds on those solutes.^[44] Hydrogen bonds between water molecules have an average lifetime of 10⁻¹¹ seconds, or 10 picoseconds.^[45]

Bifurcated and over-coordinated hydrogen bonds in water

A single hydrogen atom can participate in two hydrogen bonds. This type of bonding is called "bifurcated" (split in two or "two-forked"). It can exist, for instance, in complex organic molecules.^[46] It has been suggested that a bifurcated hydrogen atom is an essential step in water reorientation.^[47]

Acceptor-type hydrogen bonds (terminating on an oxygen's lone pairs) are more likely to form bifurcation (it is called overcoordinated oxygen, OCO) than are donor-type hydrogen bonds, beginning on the same oxygen atom's hydrogen atoms.^[48]

Other liquids

For example, hydrogen fluoride—which has three lone pairs on the F atom but only one H atom—can form only two bonds. Ammonia has the opposite problem: three hydrogen atoms but only one lone pair.

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Further manifestations of solvent hydrogen bonding

Increase in the melting point, boiling point, solubility, and viscosity of many compounds can be explained by the concept of hydrogen bonding.
Negative azeotropy of mixtures of HF and water.
The fact that ice is less dense than liquid water is due to a crystal structure stabilized by hydrogen bonds.
Dramatically higher boiling points of NH₃, H₂O, and HF compared to the heavier analogues PH₃, H₂S, and HCl, where hydrogen-bonding is absent.
Viscosity of anhydrous phosphoric acid and of glycerol.
Dimer formation in carboxylic acids and hexamer formation in hydrogen fluoride, which occur even in the gas phase, resulting in gross deviations from the ideal gas law.
Pentamer formation of water and alcohols in apolar solvents.

Hydrogen bonds in polymers

Hydrogen bonding plays an important role in determining the three-dimensional structures and the properties adopted by many proteins. Compared to the C−C, C−O, and C−N bonds that comprise most polymers, hydrogen bonds are far weaker, perhaps 5% as strong. Thus, hydrogen bonds can be broken by chemical or mechanical means while retaining the basic structure of the polymer backbone. This hierarchy of bond strengths (covalent bonds being stronger than hydrogen-bonds being stronger than van der Waals forces) is relevant in the properties of many materials.^[49]

DNA

File:DNA animation.gif

The structure of part of a DNA double helix

File:Base pair GC.svg

Hydrogen bonding between guanine and cytosine, one of two types of base pairs in DNA

In these macromolecules, bonding between parts of the same macromolecule cause it to fold into a specific shape, which helps determine the molecule's physiological or biochemical role. For example, the double helical structure of DNA is due largely to hydrogen bonding between its base pairs (as well as pi stacking interactions), which link one complementary strand to the other and enable replication.^{[citation needed]}

Proteins

In the secondary structure of proteins, hydrogen bonds form between the backbone oxygens and amide hydrogens. When the spacing of the amino acid residues participating in a hydrogen bond occurs regularly between positions i and i + 4, an alpha helix is formed. When the spacing is less, between positions i and i + 3, then a 3₁₀ helix is formed. When two strands are joined by hydrogen bonds involving alternating residues on each participating strand, a beta sheet is formed. Hydrogen bonds also play a part in forming the tertiary structure of protein through interaction of R-groups. (See also protein folding).^{[citation needed]}

Bifurcated H-bond systems are common in alpha-helical transmembrane proteins between the backbone amide C=O of residue i as the H-bond acceptor and two H-bond donors from residue i + 4: the backbone amide N−H and a side-chain hydroxyl or thiol H⁺. The energy preference of the bifurcated H-bond hydroxyl or thiol system is −14 or 167 kJ/mol (−3.4 or 40 kcal/mol) respectively. This type of bifurcated H-bond provides an intrahelical H-bonding partner for polar side-chains, such as serine, threonine, and cysteine within the hydrophobic membrane environments.^[27]

The role of hydrogen bonds in protein folding has also been linked to osmolyte-induced protein stabilization. Protective osmolytes, such as trehalose and sorbitol, shift the protein folding equilibrium toward the folded state, in a concentration dependent manner. While the prevalent explanation for osmolyte action relies on excluded volume effects that are entropic in nature, circular dichroism (CD) experiments have shown osmolyte to act through an enthalpic effect.^[50] The molecular mechanism for their role in protein stabilization is still not well established, though several mechanisms have been proposed. Computer molecular dynamics simulations suggest that osmolytes stabilize proteins by modifying the hydrogen bonds in the protein hydration layer.^[51]

Several studies have shown that hydrogen bonds play an important role for the stability between subunits in multimeric proteins. For example, a study of sorbitol dehydrogenase displayed an important hydrogen bonding network which stabilizes the tetrameric quaternary structure within the mammalian sorbitol dehydrogenase protein family.^[52]

A protein backbone hydrogen bond incompletely shielded from water attack is a dehydron. Dehydrons promote the removal of water through proteins or ligand binding. The exogenous dehydration enhances the electrostatic interaction between the amide and carbonyl groups by de-shielding their partial charges. Furthermore, the dehydration stabilizes the hydrogen bond by destabilizing the nonbonded state consisting of dehydrated isolated charges.^[53]

Wool, being a protein fibre, is held together by hydrogen bonds, causing wool to recoil when stretched. However, washing at high temperatures can permanently break the hydrogen bonds and a garment may permanently lose its shape.^[54]

Other polymers

File:Kevlar chemical structure H-bonds.svg

Para-aramid structure

File:Cellulose strand.svg

A strand of cellulose (conformation I_α), showing the hydrogen bonds (dashed) within and between cellulose molecules

The properties of many polymers are affected by hydrogen bonds within and/or between the chains. Prominent examples include cellulose and its derived fibers, such as cotton and flax. In nylon, hydrogen bonds between carbonyl and the amide NH effectively link adjacent chains, which gives the material mechanical strength. Hydrogen bonds also affect the aramid fibre, where hydrogen bonds stabilize the linear chains laterally. The chain axes are aligned along the fibre axis, making the fibres extremely stiff and strong. Hydrogen-bond networks make both polymers sensitive to humidity levels in the atmosphere because water molecules can diffuse into the surface and disrupt the network. Some polymers are more sensitive than others. Thus nylons are more sensitive than aramids, and nylon 6 more sensitive than nylon-11.^{[citation needed]}

Symmetric hydrogen bond

A symmetric hydrogen bond is a special type of hydrogen bond in which the proton is spaced exactly halfway between two identical atoms. The strength of the bond to each of those atoms is equal. It is an example of a three-center four-electron bond. This type of bond is much stronger than a "normal" hydrogen bond. The effective bond order is 0.5, so its strength is comparable to a covalent bond. It is seen in ice at high pressure, and also in the solid phase of many anhydrous acids such as hydrofluoric acid and formic acid at high pressure. It is also seen in the bifluoride ion [F···H···F]⁻. Due to severe steric constraint, the protonated form of Proton Sponge (1,8-bis(dimethylamino)naphthalene) and its derivatives also have symmetric hydrogen bonds ([N···H···N]⁺),^[55] although in the case of protonated Proton Sponge, the assembly is bent.^[56]

Dihydrogen bond

The hydrogen bond can be compared with the closely related dihydrogen bond, which is also an intermolecular bonding interaction involving hydrogen atoms. These structures have been known for some time, and well characterized by crystallography;^[57] however, an understanding of their relationship to the conventional hydrogen bond, ionic bond, and covalent bond remains unclear. Generally, the hydrogen bond is characterized by a proton acceptor that is a lone pair of electrons in nonmetallic atoms (most notably in the nitrogen, and chalcogen groups). In some cases, these proton acceptors may be pi-bonds or metal complexes. In the dihydrogen bond, however, a metal hydride serves as a proton acceptor, thus forming a hydrogen-hydrogen interaction. Neutron diffraction has shown that the molecular geometry of these complexes is similar to hydrogen bonds, in that the bond length is very adaptable to the metal complex/hydrogen donor system.^[57]

Application to drugs

The hydrogen bond is relevant to drug design. According to Lipinski's rule of five the majority of orally active drugs have no more than five hydrogen bond donors and fewer than ten hydrogen bond acceptors. These interactions exist between nitrogen–hydrogen and oxygen–hydrogen centers.^[58] Many drugs do not, however, obey these "rules".^[59]

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↑ Sun, C. Q.; Sun, Yi (2016). The Attribute of Water: Single Notion, Multiple Myths. Springer. ISBN 978-981-10-0178-9.
↑ Grunenberg, Jörg (2004). "Direct Assessment of Interresidue Forces in Watson−Crick Base Pairs Using Theoretical Compliance Constants". Journal of the American Chemical Society. 126 (50): 16310–1. Bibcode:2004JAChS.12616310G. doi:10.1021/ja046282a. PMID 15600318.
↑ Isaacs, E.D.; Shukla, A.; Platzman, P.; Hamann, D.R.; Barbiellini, B.; Tulk, C.A. (1999). "Covalency of the Hydrogen Bond in Ice: A Direct X-Ray Measurement". Physical Review Letters. 82 (3): 600–603. Bibcode:1999PhRvL..82..600I. doi:10.1103/PhysRevLett.82.600.
↑ Ghanty, Tapan K.; Staroverov, Viktor N.; Koren, Patrick R.; Davidson, Ernest R. (2000-02-01). "Is the Hydrogen Bond in Water Dimer and Ice Covalent?". Journal of the American Chemical Society. 122 (6): 1210–1214. Bibcode:2000JAChS.122.1210G. doi:10.1021/ja9937019. ISSN 0002-7863.
↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
↑ Cordier, F; Rogowski, M; Grzesiek, S; Bax, A (1999). "Observation of through-hydrogen-bond (2h)J(HC') in a perdeuterated protein". J Magn Reson. 140 (2): 510–2. Bibcode:1999JMagR.140..510C. doi:10.1006/jmre.1999.1899. PMID 10497060. S2CID 121429.
↑ Needham, Paul (2013). "Hydrogen bonding: Homing in on a tricky chemical concept". Studies in History and Philosophy of Science Part A. 44 (1): 51–65. Bibcode:2013SHPSA..44...51N. doi:10.1016/j.shpsa.2012.04.001.
↑ Pauling, L. (1960). The nature of the chemical bond and the structure of molecules and crystals; an introduction to modern structural chemistry (3rd ed.). Ithaca (NY): Cornell University Press. p. 450. ISBN 978-0-8014-0333-0.
↑ Moore, T. S.; Winmill, T. F. (1912). "The state of amines in aqueous solution". J. Chem. Soc. 101: 1635. doi:10.1039/CT9120101635.
↑ Latimer, Wendell M.; Rodebush, Worth H. (1920). "Polarity and ionization from the standpoint of the Lewis theory of valence". Journal of the American Chemical Society. 42 (7): 1419–1433. Bibcode:1920JAChS..42.1419L. doi:10.1021/ja01452a015.
↑ "11.9: Water - An Extraordinary Substance". Chemistry LibreTexts. 2017-06-29. Retrieved 2024-06-22.
↑ ^42.0 ^42.1 Jorgensen, W. L.; Madura, J. D. (1985). "Temperature and size dependence for Monte Carlo simulations of TIP4P water". Mol. Phys. 56 (6): 1381. Bibcode:1985MolPh..56.1381J. doi:10.1080/00268978500103111.
↑ Zielkiewicz, Jan (2005). "Structural properties of water: Comparison of the SPC, SPCE, TIP4P, and TIP5P models of water". J. Chem. Phys. 123 (10): 104501. Bibcode:2005JChPh.123j4501Z. doi:10.1063/1.2018637. PMID 16178604.
↑ Jencks, William; Jencks, William P. (1986). "Hydrogen Bonding between Solutes in Aqueous Solution". J. Am. Chem. Soc. 108 (14): 4196. Bibcode:1986JAChS.108.4196S. doi:10.1021/ja00274a058.
↑ Dillon, P. F. (2012). Biophysics: A Physiological Approach. Cambridge University Press. p. 37. ISBN 978-1-139-50462-1.
↑ Baron, Michel; Giorgi-Renault, Sylviane; Renault, Jean; Mailliet, Patrick; Carré, Daniel; Etienne, Jean (1984). "Hétérocycles à fonction quinone. V. Réaction anormale de la butanedione avec la diamino-1,2 anthraquinone; structure cristalline de la naphto \2,3-f] quinoxalinedione-7,12 obtenue". Can. J. Chem. 62 (3): 526–530. doi:10.1139/v84-087.
↑ Laage, Damien; Hynes, James T. (2006). "A Molecular Jump Mechanism for Water Reorientation". Science. 311 (5762): 832–5. Bibcode:2006Sci...311..832L. doi:10.1126/science.1122154. PMID 16439623. S2CID 6707413.
↑ Markovitch, Omer; Agmon, Noam (2008). "The Distribution of Acceptor and Donor Hydrogen-Bonds in Bulk Liquid Water". Molecular Physics. 106 (2): 485. Bibcode:2008MolPh.106..485M. doi:10.1080/00268970701877921. S2CID 17648714.
↑ Shiao-Wei Kuo (2018). Hydrogen Bonding in Polymer Materials. Wiley-VCH.
↑ Politi, Regina; Harries, Daniel (2010). "Enthalpically driven peptide stabilization by protective osmolytes". ChemComm. 46 (35): 6449–6451. doi:10.1039/C0CC01763A. PMID 20657920.
↑ Gilman-Politi, Regina; Harries, Daniel (2011). "Unraveling the Molecular Mechanism of Enthalpy Driven Peptide Folding by Polyol Osmolytes". Journal of Chemical Theory and Computation. 7 (11): 3816–3828. doi:10.1021/ct200455n. PMID 26598272.
↑ Hellgren, M.; Kaiser, C.; de Haij, S.; Norberg, A.; Höög, J. O. (December 2007). "A hydrogen-bonding network in mammalian sorbitol dehydrogenase stabilizes the tetrameric state and is essential for the catalytic power". Cellular and Molecular Life Sciences. 64 (23): 3129–38. doi:10.1007/s00018-007-7318-1. PMC 11136444 Check |pmc= value (help). PMID 17952367. S2CID 22090973.
↑ Fernández, A.; Rogale K.; Scott Ridgway; Scheraga H. A. (June 2004). "Inhibitor design by wrapping packing defects in HIV-1 proteins". Proceedings of the National Academy of Sciences. 101 (32): 11640–5. Bibcode:2004PNAS..10111640F. doi:10.1073/pnas.0404641101. PMC 511032. PMID 15289598.
↑ Farnworth, A.J. (1957). "A Hydrogen Bonding Mechanism for the Permanent Setting of Wool Fibers". Textile Research Journal. 27 (8): 632–640. doi:10.1177/004051755702700807.
↑ Khashayar Rajabimoghadam Yousef Darwish Umyeena Bashir Dylan Pitman Sidney Eichelberger Maxime A. Siegler Marcel Swart Isaac Garcia-Bosch Aerobic Oxidation of Alcohols by Copper Complexes Bearing Redox-Active Ligands with Tunable H-Bonding https://doi.org/10.1021/jacs.8b08748
↑ Ozeryanskii, Valery A.; Pozharskii, Alexander F.; Bieńko, Agnieszka J.; Sawka-Dobrowolska, Wanda; Sobczyk, Lucjan (2005-03-01). "[NHN]+ Hydrogen Bonding in Protonated 1,8-Bis(dimethylamino)-2,7-dimethoxynaphthalene. X-ray Diffraction, Infrared, and Theoretical ab Initio and DFT Studies". The Journal of Physical Chemistry A. 109 (8): 1637–1642. Bibcode:2005JPCA..109.1637O. doi:10.1021/jp040618l. ISSN 1089-5639. PMID 16833488.
↑ ^57.0 ^57.1 Crabtree, Robert H.; Siegbahn, Per E. M.; Eisenstein, Odile; Rheingold, Arnold L.; Koetzle, Thomas F. (1996). "A New Intermolecular Interaction: Unconventional Hydrogen Bonds with Element-Hydride Bonds as Proton Acceptor". Acc. Chem. Res. 29 (7): 348–354. doi:10.1021/ar950150s. PMID 19904922.
↑ Lipinski CA (December 2004). "Lead- and drug-like compounds: the rule-of-five revolution". Drug Discovery Today: Technologies. 1 (4): 337–341. doi:10.1016/j.ddtec.2004.11.007. PMID 24981612.
↑ o′Hagan, Steve; Swainston, Neil; Handl, Julia; Kell, Douglas B. (2015). "A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs". Metabolomics. 11 (2): 323–339. doi:10.1007/s11306-014-0733-z. PMC 4342520. PMID 25750602.

External links

The Bubble Wall (Audio slideshow from the National High Magnetic Field Laboratory explaining cohesion, surface tension and hydrogen bonds)
isotopic effect on bond dynamics

Template:Chemical bonds

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[20] Data obtained using molecular dynamics as detailed in the reference and should be compared to 7.9 kJ/mol for bulk water, obtained using the same calculation.Markovitch, Omer; Agmon, Noam (2007). "Structure and energetics of the hydronium hydration shells" (PDF). J. Phys. Chem. A. 111 (12): 2253–2256. Bibcode:2007JPCA..111.2253M. CiteSeerX 10.1.1.76.9448. doi:10.1021/jp068960g. PMID 17388314. Archived from the original (PDF) on 2014-08-13. Retrieved 2017-10-25.

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[23] Lin, Xuhui; Zhang, Huaiyu; Jiang, Xiaoyu; Wu, Wei; Mo, Yirong (2017). "The Origin of the Non-Additivity in Resonance-Assisted Hydrogen Bond Systems". The Journal of Physical Chemistry A. 121 (44): 8535–8541. Bibcode:2017JPCA..121.8535L. doi:10.1021/acs.jpca.7b09425. PMID 29048895.

[24] Legon, A. C.; Millen, D. J. (1987). "Angular geometries and other properties of hydrogen-bonded dimers: a simple electrostatic interpretation of the success of the electron-pair model". Chemical Society Reviews. 16: 467. doi:10.1039/CS9871600467.

[25] Friebolin, H., "Basic One- and Two- Dimensional NMR Spectroscopy, 4th ed.," VCH: Weinheim, 2008. ISBN 978-3-527-31233-7

[26] Hobza P, Havlas Z (2000). "Blue-Shifting Hydrogen Bonds". Chem. Rev. 100 (11): 4253–4264. doi:10.1021/cr990050q. PMID 11749346.

[Feldblum_2014_4085–4090-27] 27.0 ^27.1 Feldblum, Esther S.; Arkin, Isaiah T. (2014). "Strength of a bifurcated H bond". Proceedings of the National Academy of Sciences. 111 (11): 4085–4090. Bibcode:2014PNAS..111.4085F. doi:10.1073/pnas.1319827111. PMC 3964065. PMID 24591597.

[cowan-28] Cowan ML; Bruner BD; Huse N; et al. (2005). "Ultrafast memory loss and energy redistribution in the hydrogen bond network of liquid H₂O". Nature. 434 (7030): 199–202. Bibcode:2005Natur.434..199C. doi:10.1038/nature03383. PMID 15758995. S2CID 4396493.

[1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-29] 29.0 ^29.1 Luo, Jiangshui; Jensen, Annemette H.; Brooks, Neil R.; Sniekers, Jeroen; Knipper, Martin; Aili, David; Li, Qingfeng; Vanroy, Bram; Wübbenhorst, Michael; Yan, Feng; Van Meervelt, Luc; Shao, Zhigang; Fang, Jianhua; Luo, Zheng-Hong; De Vos, Dirk E.; Binnemans, Koen; Fransaer, Jan (2015). "1,2,4-Triazolium perfluorobutanesulfonate as an archetypal pure protic organic ionic plastic crystal electrolyte for all-solid-state fuel cells". Energy & Environmental Science. 8 (4): 1276. Bibcode:2015EnEnS...8.1276L. doi:10.1039/C4EE02280G. S2CID 84176511.

[30] Weinhold, Frank; Klein, Roger A. (2014). "What is a hydrogen bond? Resonance covalency in the supramolecular domain". Chemistry Education Research and Practice. 15 (3): 276–285. doi:10.1039/c4rp00030g.

[31] Sun, C. Q.; Sun, Yi (2016). The Attribute of Water: Single Notion, Multiple Myths. Springer. ISBN 978-981-10-0178-9.

[32] Grunenberg, Jörg (2004). "Direct Assessment of Interresidue Forces in Watson−Crick Base Pairs Using Theoretical Compliance Constants". Journal of the American Chemical Society. 126 (50): 16310–1. Bibcode:2004JAChS.12616310G. doi:10.1021/ja046282a. PMID 15600318.

[33] Isaacs, E.D.; Shukla, A.; Platzman, P.; Hamann, D.R.; Barbiellini, B.; Tulk, C.A. (1999). "Covalency of the Hydrogen Bond in Ice: A Direct X-Ray Measurement". Physical Review Letters. 82 (3): 600–603. Bibcode:1999PhRvL..82..600I. doi:10.1103/PhysRevLett.82.600.

[34] Ghanty, Tapan K.; Staroverov, Viktor N.; Koren, Patrick R.; Davidson, Ernest R. (2000-02-01). "Is the Hydrogen Bond in Water Dimer and Ice Covalent?". Journal of the American Chemical Society. 122 (6): 1210–1214. Bibcode:2000JAChS.122.1210G. doi:10.1021/ja9937019. ISSN 0002-7863.

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[36] Cordier, F; Rogowski, M; Grzesiek, S; Bax, A (1999). "Observation of through-hydrogen-bond (2h)J(HC') in a perdeuterated protein". J Magn Reson. 140 (2): 510–2. Bibcode:1999JMagR.140..510C. doi:10.1006/jmre.1999.1899. PMID 10497060. S2CID 121429.

[37] Needham, Paul (2013). "Hydrogen bonding: Homing in on a tricky chemical concept". Studies in History and Philosophy of Science Part A. 44 (1): 51–65. Bibcode:2013SHPSA..44...51N. doi:10.1016/j.shpsa.2012.04.001.

[38] Pauling, L. (1960). The nature of the chemical bond and the structure of molecules and crystals; an introduction to modern structural chemistry (3rd ed.). Ithaca (NY): Cornell University Press. p. 450. ISBN 978-0-8014-0333-0.

[39] Moore, T. S.; Winmill, T. F. (1912). "The state of amines in aqueous solution". J. Chem. Soc. 101: 1635. doi:10.1039/CT9120101635.

[40] Latimer, Wendell M.; Rodebush, Worth H. (1920). "Polarity and ionization from the standpoint of the Lewis theory of valence". Journal of the American Chemical Society. 42 (7): 1419–1433. Bibcode:1920JAChS..42.1419L. doi:10.1021/ja01452a015.

[41] "11.9: Water - An Extraordinary Substance". Chemistry LibreTexts. 2017-06-29. Retrieved 2024-06-22.

[Jorgensen1985-42] 42.0 ^42.1 Jorgensen, W. L.; Madura, J. D. (1985). "Temperature and size dependence for Monte Carlo simulations of TIP4P water". Mol. Phys. 56 (6): 1381. Bibcode:1985MolPh..56.1381J. doi:10.1080/00268978500103111.

[43] Zielkiewicz, Jan (2005). "Structural properties of water: Comparison of the SPC, SPCE, TIP4P, and TIP5P models of water". J. Chem. Phys. 123 (10): 104501. Bibcode:2005JChPh.123j4501Z. doi:10.1063/1.2018637. PMID 16178604.

[44] Jencks, William; Jencks, William P. (1986). "Hydrogen Bonding between Solutes in Aqueous Solution". J. Am. Chem. Soc. 108 (14): 4196. Bibcode:1986JAChS.108.4196S. doi:10.1021/ja00274a058.

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[46] Baron, Michel; Giorgi-Renault, Sylviane; Renault, Jean; Mailliet, Patrick; Carré, Daniel; Etienne, Jean (1984). "Hétérocycles à fonction quinone. V. Réaction anormale de la butanedione avec la diamino-1,2 anthraquinone; structure cristalline de la naphto \2,3-f] quinoxalinedione-7,12 obtenue". Can. J. Chem. 62 (3): 526–530. doi:10.1139/v84-087.

[47] Laage, Damien; Hynes, James T. (2006). "A Molecular Jump Mechanism for Water Reorientation". Science. 311 (5762): 832–5. Bibcode:2006Sci...311..832L. doi:10.1126/science.1122154. PMID 16439623. S2CID 6707413.

[48] Markovitch, Omer; Agmon, Noam (2008). "The Distribution of Acceptor and Donor Hydrogen-Bonds in Bulk Liquid Water". Molecular Physics. 106 (2): 485. Bibcode:2008MolPh.106..485M. doi:10.1080/00268970701877921. S2CID 17648714.

[49] Shiao-Wei Kuo (2018). Hydrogen Bonding in Polymer Materials. Wiley-VCH.

[50] Politi, Regina; Harries, Daniel (2010). "Enthalpically driven peptide stabilization by protective osmolytes". ChemComm. 46 (35): 6449–6451. doi:10.1039/C0CC01763A. PMID 20657920.

[51] Gilman-Politi, Regina; Harries, Daniel (2011). "Unraveling the Molecular Mechanism of Enthalpy Driven Peptide Folding by Polyol Osmolytes". Journal of Chemical Theory and Computation. 7 (11): 3816–3828. doi:10.1021/ct200455n. PMID 26598272.

[52] Hellgren, M.; Kaiser, C.; de Haij, S.; Norberg, A.; Höög, J. O. (December 2007). "A hydrogen-bonding network in mammalian sorbitol dehydrogenase stabilizes the tetrameric state and is essential for the catalytic power". Cellular and Molecular Life Sciences. 64 (23): 3129–38. doi:10.1007/s00018-007-7318-1. PMC 11136444 Check |pmc= value (help). PMID 17952367. S2CID 22090973.

[53] Fernández, A.; Rogale K.; Scott Ridgway; Scheraga H. A. (June 2004). "Inhibitor design by wrapping packing defects in HIV-1 proteins". Proceedings of the National Academy of Sciences. 101 (32): 11640–5. Bibcode:2004PNAS..10111640F. doi:10.1073/pnas.0404641101. PMC 511032. PMID 15289598.

[54] Farnworth, A.J. (1957). "A Hydrogen Bonding Mechanism for the Permanent Setting of Wool Fibers". Textile Research Journal. 27 (8): 632–640. doi:10.1177/004051755702700807.

[55] Khashayar Rajabimoghadam Yousef Darwish Umyeena Bashir Dylan Pitman Sidney Eichelberger Maxime A. Siegler Marcel Swart Isaac Garcia-Bosch Aerobic Oxidation of Alcohols by Copper Complexes Bearing Redox-Active Ligands with Tunable H-Bonding https://doi.org/10.1021/jacs.8b08748

[56] Ozeryanskii, Valery A.; Pozharskii, Alexander F.; Bieńko, Agnieszka J.; Sawka-Dobrowolska, Wanda; Sobczyk, Lucjan (2005-03-01). "[NHN]+ Hydrogen Bonding in Protonated 1,8-Bis(dimethylamino)-2,7-dimethoxynaphthalene. X-ray Diffraction, Infrared, and Theoretical ab Initio and DFT Studies". The Journal of Physical Chemistry A. 109 (8): 1637–1642. Bibcode:2005JPCA..109.1637O. doi:10.1021/jp040618l. ISSN 1089-5639. PMID 16833488.

[crab-57] 57.0 ^57.1 Crabtree, Robert H.; Siegbahn, Per E. M.; Eisenstein, Odile; Rheingold, Arnold L.; Koetzle, Thomas F. (1996). "A New Intermolecular Interaction: Unconventional Hydrogen Bonds with Element-Hydride Bonds as Proton Acceptor". Acc. Chem. Res. 29 (7): 348–354. doi:10.1021/ar950150s. PMID 19904922.

[Lipinski_2004-58] Lipinski CA (December 2004). "Lead- and drug-like compounds: the rule-of-five revolution". Drug Discovery Today: Technologies. 1 (4): 337–341. doi:10.1016/j.ddtec.2004.11.007. PMID 24981612.

[59] ′Hagan, Steve; Swainston, Neil; Handl, Julia; Kell, Douglas B. (2015). "A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs". Metabolomics. 11 (2): 323–339. doi:10.1007/s11306-014-0733-z. PMC 4342520. PMID 25750602.

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@@ Line 2: / Line 2: @@
 [[Image:3D model hydrogen bonds in water.svg|right|thumb|Model of hydrogen bonds (1) between molecules of [[Properties of water|water]]]]
-[[File:NTCDI AFM2a.jpg|thumb|[[Non-contact atomic force microscopy|AFM]] image of [[naphthalenetetracarboxylic diimide]] molecules on silver-terminated silicon, interacting via hydrogen bonding, taken at 77 K.<ref>{{cite journal|doi=10.1038/ncomms4931|title=Mapping the force field of a hydrogen-bonded assembly|journal=Nature Communications|volume=5|pages=3931|year=2014|last1=Sweetman|first1=A. M.|last2=Jarvis|first2=S. P.|last3=Sang|first3=Hongqian|last4=Lekkas|first4=I.|last5=Rahe|first5=P.|last6=Wang|first6=Yu|last7=Wang|first7=Jianbo|last8=Champness|first8=N.R.|last9=Kantorovich|first9=L.|last10=Moriarty|first10=P.|bibcode=2014NatCo...5.3931S|pmid=24875276|pmc=4050271}}</ref> ("Hydrogen bonds" in the top image are exaggerated by artifacts of the imaging technique.<ref>{{Cite journal|last1=Hapala|first1=Prokop|last2=Kichin|first2=Georgy|last3=Wagner|first3=Christian|last4=Tautz|first4=F. Stefan|last5=Temirov|first5=Ruslan|last6=Jelínek|first6=Pavel|date=2014-08-19|title=Mechanism of high-resolution STM/AFM imaging with functionalized tips|journal=Physical Review B|volume=90|issue=8|pages=085421|doi=10.1103/PhysRevB.90.085421|arxiv=1406.3562|bibcode=2014PhRvB..90h5421H|s2cid=53610973}}</ref><ref>{{cite journal |last1=De Luca |first1=S. |last2=Chen |first2=F. |last3=Seal |first3=P. |last4=Stenzel |first4=M. H. |last5=Smith |first5=S. C. |date=2017 |title=Binding and Release between Polymeric Carrier and Protein Drug: pH-Mediated Interplay of Coulomb Forces, Hydrogen Bonding, van der Waals Interactions, and Entropy |url=https://doi.org/10.1021/acs.biomac.7b00657 |journal=Biomacromolecules |volume=18 |issue=11 |pages=3665–3677 | pmid=28880549 | doi=10.1021/acs.biomac.7b00657|hdl=1959.4/unsworks_55160 |hdl-access=free }}</ref><ref>{{Cite journal|last1=Hämäläinen|first1=Sampsa K.|last2=van der Heijden|first2=Nadine|last3=van der Lit|first3=Joost|last4=den Hartog|first4=Stephan|last5=Liljeroth|first5=Peter|last6=Swart|first6=Ingmar|date=2014-10-31|title=Intermolecular Contrast in Atomic Force Microscopy Images without Intermolecular Bonds|journal=Physical Review Letters|volume=113|issue=18|pages=186102|doi=10.1103/PhysRevLett.113.186102|pmid=25396382|url=http://dspace.library.uu.nl:8080/handle/1874/307996|bibcode=2014PhRvL.113r6102H|url-status=dead|archive-url=https://web.archive.org/web/20180120232850/http://dspace.library.uu.nl:8080/handle/1874/307996|archive-date=2018-01-20|arxiv=1410.1933|hdl=1874/307996|s2cid=8309018|access-date=2017-08-30}}</ref>)]]
+[[File:NTCDI AFM2a.jpg|thumb|[[Non-contact atomic force microscopy|AFM]] image of [[naphthalenetetracarboxylic diimide]] molecules on silver-terminated silicon, interacting via hydrogen bonding, taken at 77 K.<ref>{{cite journal|doi=10.1038/ncomms4931|title=Mapping the force field of a hydrogen-bonded assembly|journal=Nature Communications|volume=5|page=3931|year=2014|last1=Sweetman|first1=A. M.|last2=Jarvis|first2=S. P.|last3=Sang|first3=Hongqian|last4=Lekkas|first4=I.|last5=Rahe|first5=P.|last6=Wang|first6=Yu|last7=Wang|first7=Jianbo|last8=Champness|first8=N.R.|last9=Kantorovich|first9=L.|last10=Moriarty|first10=P.|bibcode=2014NatCo...5.3931S|pmid=24875276|pmc=4050271}}</ref> ("Hydrogen bonds" in the top image are exaggerated by artifacts of the imaging technique.<ref>{{Cite journal|last1=Hapala|first1=Prokop|last2=Kichin|first2=Georgy|last3=Wagner|first3=Christian|last4=Tautz|first4=F. Stefan|last5=Temirov|first5=Ruslan|last6=Jelínek|first6=Pavel|date=2014-08-19|title=Mechanism of high-resolution STM/AFM imaging with functionalized tips|journal=Physical Review B|volume=90|issue=8|article-number=085421|doi=10.1103/PhysRevB.90.085421|arxiv=1406.3562|bibcode=2014PhRvB..90h5421H|s2cid=53610973}}</ref><ref>{{cite journal |last1=De Luca |first1=S. |last2=Chen |first2=F. |last3=Seal |first3=P. |last4=Stenzel |first4=M. H. |last5=Smith |first5=S. C. |date=2017 |title=Binding and Release between Polymeric Carrier and Protein Drug: pH-Mediated Interplay of Coulomb Forces, Hydrogen Bonding, van der Waals Interactions, and Entropy |journal=Biomacromolecules |volume=18 |issue=11 |pages=3665–3677 | pmid=28880549 | doi=10.1021/acs.biomac.7b00657|hdl=1959.4/unsworks_55160 |hdl-access=free }}</ref><ref>{{Cite journal|last1=Hämäläinen|first1=Sampsa K.|last2=van der Heijden|first2=Nadine|last3=van der Lit|first3=Joost|last4=den Hartog|first4=Stephan|last5=Liljeroth|first5=Peter|last6=Swart|first6=Ingmar|date=2014-10-31|title=Intermolecular Contrast in Atomic Force Microscopy Images without Intermolecular Bonds|journal=Physical Review Letters|volume=113|issue=18|article-number=186102|doi=10.1103/PhysRevLett.113.186102|pmid=25396382|url=http://dspace.library.uu.nl:8080/handle/1874/307996|bibcode=2014PhRvL.113r6102H|archive-url=https://web.archive.org/web/20180120232850/http://dspace.library.uu.nl:8080/handle/1874/307996|archive-date=2018-01-20|arxiv=1410.1933|hdl=1874/307996|s2cid=8309018|access-date=2017-08-30}}</ref>)]]
 In [[chemistry]], a '''hydrogen bond''' ('''H-bond''') is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely [[electrostatic force]]'''.''' It occurs when a [[hydrogen]] (H) atom, [[Covalent bond|covalently]] bonded to a more [[Electronegativity|electronegative]] donor atom or group ('''Dn'''), interacts with another electronegative atom bearing a [[lone pair]] of electrons—the hydrogen bond acceptor ('''Ac'''). Unlike simple [[Dipole–dipole attraction|dipole–dipole]] interactions, hydrogen bonding arises from charge transfer (nB → σ*AH), [[Atomic orbital|orbital]] interactions, and quantum mechanical [[Delocalized electron|delocalization]], making it a '''resonance-assisted interaction''' rather than a mere electrostatic attraction.<ref name=":1">{{Cite journal |last1=Weinhold |first1=Frank |last2=Klein |first2=Roger A. |date=2014-07-08 |title=What is a hydrogen bond? Resonance covalency in the supramolecular domain |url=https://pubs.rsc.org/en/content/articlelanding/2014/rp/c4rp00030g |journal=Chemistry Education Research and Practice |language=en |volume=15 |issue=3 |pages=276–285 |doi=10.1039/C4RP00030G |issn=1756-1108|url-access=subscription }}</ref>
-The general notation for hydrogen bonding is '''Dn−H···Ac''', where the solid line represents a polar covalent bond, and the dotted or dashed line indicates the hydrogen bond.<ref name=":0">{{Cite journal |last1=Arunan |first1=Elangannan |last2=Desiraju |first2=Gautam R. |last3=Klein |first3=Roger A. |last4=Sadlej |first4=Joanna |last5=Scheiner |first5=Steve |last6=Alkorta |first6=Ibon |last7=Clary |first7=David C. |last8=Crabtree |first8=Robert H. |last9=Dannenberg |first9=Joseph J. |date=2011-07-08 |title=Definition of the hydrogen bond (IUPAC Recommendations 2011) |journal=Pure and Applied Chemistry |volume=83 |issue=8 |pages=1637–1641 |doi=10.1351/PAC-REC-10-01-02 |issn=1365-3075 |s2cid=97688573 |doi-access=free}}</ref> The most frequent donor and acceptor atoms are [[nitrogen]] (N), [[oxygen]] (O), and [[fluorine]] (F), due to their high electronegativity and ability to engage in stronger hydrogen bonding.
+The general notation for hydrogen bonding is '''Dn−H···Ac''', where the solid line represents a polar covalent bond, and the three dots indicate the hydrogen bond.<ref name=":0">{{Cite journal |last1=Arunan |first1=Elangannan |last2=Desiraju |first2=Gautam R. |last3=Klein |first3=Roger A. |last4=Sadlej |first4=Joanna |last5=Scheiner |first5=Steve |last6=Alkorta |first6=Ibon |last7=Clary |first7=David C. |last8=Crabtree |first8=Robert H. |last9=Dannenberg |first9=Joseph J. |date=2011-07-08 |title=Definition of the hydrogen bond (IUPAC Recommendations 2011) |journal=Pure and Applied Chemistry |volume=83 |issue=8 |pages=1637–1641 |doi=10.1351/PAC-REC-10-01-02 |issn=1365-3075 |s2cid=97688573 |doi-access=free|hdl=11104/0218602 |hdl-access=free }}</ref> '''Hydrogen bond donors''' have a protic hydrogen attached to an electronegative atom such as [[nitrogen]] (N), [[oxygen]] (O), and [[fluorine]] (F).  '''Hydrogen bond acceptors''' have a lone pair of electrons, such as [[amine]]s, [[carboxylate]]s, and water.
 The term "hydrogen bond" is generally used for well-defined, localized interactions with significant charge transfer and orbital overlap, such as those in DNA base pairing or ice. In contrast, "hydrogen-bonding interactions" is a broader term used when the interaction is weaker, more dynamic, or delocalized, such as in liquid water, supramolecular assemblies (e.g.: [[Lipid bilayer|lipid membranes]], [[Protein–protein interaction|protein-protein interactions]]), or weak C-H···O interactions. This distinction is particularly relevant in [[structural biology]], [[materials science]], and [[computational chemistry]], where hydrogen bonding spans a continuum from weak van der Waals-like interactions to nearly covalent bonding.<ref name=":1" />
-Hydrogen bonding can occur between separate molecules (intermolecular) or within different parts of the same molecule (intramolecular).<ref>Pimentel, G. ''The Hydrogen Bond''  Franklin Classics, 2018), {{ISBN|0343171600}}</ref><ref>Jeffrey, G. A.; ''An introduction to hydrogen bonding''; Oxford university press New York, 1997. {{ISBN|0195095499}}</ref><ref>Jeffrey, G. A.; Saenger, W. ''Hydrogen bonding in biological structures''; Springer: Berlin, '''1994, 2012'''  Springer; {{ISBN|3540579036}}</ref><ref>{{GoldBookRef|file=H02899|title=hydrogen bond}}</ref> Its strength varies considerably, depending on geometry, environment, and the donor-acceptor pair, typically ranging from 1 to 40 kcal/mol.<ref name="The Hydrogen Bond in the Solid Stat">{{cite journal |last1=Steiner |first1=Thomas |year=2002 |title=The Hydrogen Bond in the Solid State |journal=[[Angew. Chem. Int. Ed.]] |volume=41 |issue=1 |pages=48–76 |doi=10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U |pmid=12491444}}</ref> This places hydrogen bonds stronger than [[Van der Waals force|van der Waals interactions]] but generally weaker than [[Covalent bond|covalent]] or [[Ionic bonding|ionic bonds]].
+Hydrogen bonding can occur between separate molecules (intermolecular) or within different parts of the same molecule (intramolecular).<ref>Pimentel, G. ''The Hydrogen Bond''  Franklin Classics, 2018), {{ISBN|0343171600}}</ref><ref>Jeffrey, G. A.; ''An introduction to hydrogen bonding''; Oxford university press New York, 1997. {{ISBN|0195095499}}</ref><ref>Jeffrey, G. A.; Saenger, W. ''Hydrogen bonding in biological structures''; Springer: Berlin, '''1994, 2012'''  Springer; {{ISBN|3540579036}}</ref><ref>{{GoldBookRef|file=H02899|title=hydrogen bond}}</ref> Its strength varies considerably, depending on geometry, environment, and the donor-acceptor pair, typically ranging from {{cvt|1|to|40|kcal/mol|order=flip}}.<ref name="The Hydrogen Bond in the Solid State">{{cite journal |last1=Steiner |first1=Thomas |year=2002 |title=The Hydrogen Bond in the Solid State |journal=[[Angew. Chem. Int. Ed.]] |volume=41 |issue=1 |pages=48–76 |doi=10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO;2-U |pmid=12491444}}</ref> This places hydrogen bonds stronger than [[Van der Waals force|van der Waals interactions]] but generally weaker than [[Covalent bond|covalent]] or [[Ionic bonding|ionic bonds]].
 Hydrogen bonding plays a fundamental role in chemistry, biology, and materials science. It is responsible for the anomalously high boiling point of water, the stabilization of protein and nucleic acid structures, and key properties of materials like paper, wool, and hydrogels. In biological systems, hydrogen bonds mediate molecular recognition, enzyme catalysis, and DNA replication, while in materials science, they contribute to self-assembly, adhesion, and supramolecular organization.
@@ Line 25: / Line 25: @@
 Hydrogen bonds arise from a combination of electrostatics (multipole-multipole and multipole-induced multipole interactions), covalency (charge transfer by orbital overlap), and dispersion ([[London dispersion force|London forces]]).<ref name=":0" />
-In weaker hydrogen bonds,<ref>Desiraju, G. R. and Steiner, T. The Weak Hydrogen Bond: In Structural Chemistry and Biology, International Union of Crystallography;'''2001''', {{ISBN|0198509707}}</ref> hydrogen atoms tend to bond to elements such as sulfur (S) or chlorine (Cl); even carbon (C) can serve as a donor, particularly when the carbon or one of its neighbors is electronegative (e.g., in chloroform, aldehydes and terminal acetylenes).<ref>Nishio, M.; Hirota, M.; Umezawa, Y. ''The CH–π Interactions''; Wiley-VCH, New York, 1998. •  Wiley-VCH; 1998) {{ISBN|0471252905}}</ref><ref>{{cite journal | last1 = Nishio | first1 = M | year = 2011 | title = The CH/[small pi] hydrogen bond in chemistry. "Title | journal = Phys. Chem. Chem. Phys. | volume = 13 | issue = 31 | pages = 13873–13900 | doi=10.1039/c1cp20404a| pmid = 21611676 }}</ref> Gradually, it was recognized that there are many examples of weaker hydrogen bonding involving donor other than N, O, or F and/or acceptor Ac with electronegativity approaching that of hydrogen (rather than being much more electronegative). Although weak (≈1&nbsp;kcal/mol), "non-traditional" hydrogen bonding interactions are ubiquitous and influence structures of many kinds of materials.{{cn|date=June 2023}}
+In weaker hydrogen bonds,<ref>Desiraju, G. R. and Steiner, T. The Weak Hydrogen Bond: In Structural Chemistry and Biology, International Union of Crystallography;'''2001''', {{ISBN|0198509707}}</ref> hydrogen atoms tend to bond to elements such as sulfur (S) or chlorine (Cl); even carbon (C) can serve as a donor, particularly when the carbon or one of its neighbors is electronegative (e.g., in chloroform, aldehydes and terminal acetylenes).<ref>Nishio, M.; Hirota, M.; Umezawa, Y. ''The CH–π Interactions''; Wiley-VCH, New York, 1998. •  Wiley-VCH; 1998) {{ISBN|0471252905}}</ref><ref>{{cite journal | last1 = Nishio | first1 = M | year = 2011 | title = The CH/[small pi] hydrogen bond in chemistry. "Title | journal = Phys. Chem. Chem. Phys. | volume = 13 | issue = 31 | pages = 13873–13900 | doi=10.1039/c1cp20404a| pmid = 21611676 }}</ref> Gradually, it was recognized that there are many examples of weaker hydrogen bonding involving donor other than N, O, or F and/or acceptor Ac with electronegativity approaching that of hydrogen (rather than being much more electronegative). Although weak (about {{cvt|1|kcal/mol|order=flip}}), "non-traditional" hydrogen bonding interactions are ubiquitous and influence structures of many kinds of materials.{{cn|date=June 2023}}
 The definition of hydrogen bonding has gradually broadened over time to include these weaker attractive interactions. In 2011, an [[IUPAC]] Task Group recommended a modern evidence-based definition of hydrogen bonding, which was published in the IUPAC journal ''[[Pure and Applied Chemistry]]''. This definition specifies:
-{{blockquote|The hydrogen bond is an attractive interaction between a hydrogen atom from a molecule or a molecular fragment {{chem2|X\sH}} in which X is more electronegative than H, and an atom or a group of atoms in the same or another molecule, in which there is evidence of bond formation.<ref name="arunen2011">{{cite journal|title = Definition of the hydrogen bond|journal = [[Pure Appl. Chem.]]|year = 2011|volume = 83|issue = 8|pages = 1637–1641|doi = 10.1351/PAC-REC-10-01-02 |last1 = Arunan|first1 = Elangannan|last2 = Desiraju|first2 = Gautam R.|last3 = Klein|first3 = Roger A.|last4 = Sadlej|first4 = Joanna|last5 = Scheiner|first5 = Steve|last6 = Alkorta|first6 = Ibon|last7 = Clary|first7 = David C.|last8 = Crabtree|first8 = Robert H.|last9 = Dannenberg|first9 = Joseph J.|last10 = Hobza|first10 = Pavel|last11 = Kjaergaard|first11 = Henrik G.|last12 = Legon|first12 = Anthony C.|last13 = Mennucci|first13 = Benedetta|last14 = Nesbitt|first14 = David J.|s2cid = 97688573|doi-access = free}}</ref>}}
+{{blockquote|The hydrogen bond is an attractive interaction between a hydrogen atom from a molecule or a molecular fragment {{chem2|X\sH}} in which X is more electronegative than H, and an atom or a group of atoms in the same or another molecule, in which there is evidence of bond formation.<ref name="arunen2011">{{cite journal|title = Definition of the hydrogen bond|journal = [[Pure Appl. Chem.]]|year = 2011|volume = 83|issue = 8|pages = 1637–1641|doi = 10.1351/PAC-REC-10-01-02 |last1 = Arunan|first1 = Elangannan|last2 = Desiraju|first2 = Gautam R.|last3 = Klein|first3 = Roger A.|last4 = Sadlej|first4 = Joanna|last5 = Scheiner|first5 = Steve|last6 = Alkorta|first6 = Ibon|last7 = Clary|first7 = David C.|last8 = Crabtree|first8 = Robert H.|last9 = Dannenberg|first9 = Joseph J.|last10 = Hobza|first10 = Pavel|last11 = Kjaergaard|first11 = Henrik G.|last12 = Legon|first12 = Anthony C.|last13 = Mennucci|first13 = Benedetta|last14 = Nesbitt|first14 = David J.|s2cid = 97688573|doi-access = free|hdl = 11104/0218602|hdl-access = free}}</ref>}}
 ===Bond strength===
-Hydrogen bonds can vary in strength from weak (1–2&nbsp;kJ/mol) to strong (161.5&nbsp;kJ/mol in the [[bifluoride]] ion, {{chem2|HF2-}}).<ref name=halide>{{cite journal|doi=10.1021/ic00182a010|title=Gas-phase bihalide and pseudobihalide ions. An ion cyclotron resonance determination of hydrogen bond energies in XHY- species (X, Y = F, Cl, Br, CN)|year=1984|last1=Larson|first1=J. W.|last2=McMahon|first2=T. B.|journal=Inorganic Chemistry|volume=23|issue=14|pages=2029–2033|title-link=ion cyclotron resonance}}</ref><ref name= Emsley>{{cite journal|author = Emsley, J.|title = Very Strong Hydrogen Bonds|journal = [[Chemical Society Reviews]]|year = 1980|volume = 9|issue = 1|pages = 91–124|doi = 10.1039/cs9800900091}}</ref> Typical [[Enthalpy|enthalpies]] in vapor include:<ref>V. David, N. Grinberg, S. C. Moldoveanu in ''Advances in Chromatography Volume 54'' (Eds.: E. Grushka, N. Grinberg), CRC Press, Boca Raton, '''2018''', chapter 3.</ref>
+Hydrogen bonds can vary in strength from weak (1–2&nbsp;kJ/mol) to strong (161.5&nbsp;kJ/mol in the [[bifluoride]] ion, HF<sub>2</sub><sup>-</sup>).<ref name=halide>{{cite journal|doi=10.1021/ic00182a010|title=Gas-phase bihalide and pseudobihalide ions. An ion cyclotron resonance determination of hydrogen bond energies in XHY- species (X, Y = F, Cl, Br, CN)|year=1984|last1=Larson|first1=J. W.|last2=McMahon|first2=T. B.|journal=Inorganic Chemistry|volume=23|issue=14|pages=2029–2033|title-link=ion cyclotron resonance}}</ref><ref name= Emsley>{{cite journal|author = Emsley, J.|title = Very Strong Hydrogen Bonds|journal = [[Chemical Society Reviews]]|year = 1980|volume = 9|issue = 1|pages = 91–124|doi = 10.1039/cs9800900091}}</ref> Typical [[Enthalpy|enthalpies]] in vapor include:<ref>V. David, N. Grinberg, S. C. Moldoveanu in ''Advances in Chromatography Volume 54'' (Eds.: E. Grushka, N. Grinberg), CRC Press, Boca Raton, '''2018''', chapter 3.</ref>
-* {{chem2|F\sH***:F-}}  (161.5&nbsp;kJ/mol or 38.6&nbsp;kcal/mol), illustrated uniquely by {{chem2|HF2-}}
+* {{chem2|F\sH***F-}}  ({{cvt|161.5|kJ/mol}}), illustrated uniquely by HF<sub>2</sub><sup>-</sup>
-* {{chem2|O\sH***:N}}  (29&nbsp;kJ/mol or 6.9&nbsp;kcal/mol), illustrated water-ammonia
+* {{chem2|O\sH***N}}  ({{cvt|29|kJ/mol}}), illustrated water-ammonia
-* {{chem2|O\sH***:O}}  (21&nbsp;kJ/mol or 5.0&nbsp;kcal/mol), illustrated water-water, alcohol-alcohol
+* {{chem2|O\sH***O}}  ({{cvt|21|kJ/mol}}), illustrated water-water, alcohol-alcohol
-* {{chem2|N\sH***:N}}  (13&nbsp;kJ/mol or 3.1&nbsp;kcal/mol), illustrated by ammonia-ammonia
+* {{chem2|N\sH***N}}  ({{cvt|13|kJ/mol}}), illustrated by ammonia-ammonia
-* {{chem2|N\sH***:O}}  (8&nbsp;kJ/mol or 1.9&nbsp;kcal/mol), illustrated water-amide
+* {{chem2|N\sH***O}}  ({{cvt|8|kJ/mol}}), illustrated water-amide
-* {{chem2|OH3+***:OH2}}  (18&nbsp;kJ/mol<ref>Data obtained using [[molecular dynamics]] as detailed in the reference and should be compared to 7.9 kJ/mol for bulk water, obtained using the same calculation.{{cite journal|title = Structure and energetics of the hydronium hydration shells|author1 = Markovitch, Omer|author2 = Agmon, Noam|journal = [[J. Phys. Chem. A]]|year = 2007|volume = 111|issue = 12|pages = 2253–2256|doi = 10.1021/jp068960g|pmid = 17388314|bibcode = 2007JPCA..111.2253M|url = http://www.fh.huji.ac.il/~agmon/Fullpaper/JPCA111-2253.pdf|url-status = dead|archive-url = https://web.archive.org/web/20140813174617/http://www.fh.huji.ac.il/%7Eagmon/Fullpaper/JPCA111-2253.pdf|archive-date = 2014-08-13|citeseerx = 10.1.1.76.9448|access-date = 2017-10-25}}</ref> or 4.3&nbsp;kcal/mol)
+* {{chem2|OH3+***OH2}}  ({{cvt|18|kJ/mol}})<ref>Data obtained using [[molecular dynamics]] as detailed in the reference and should be compared to 7.9 kJ/mol for bulk water, obtained using the same calculation.{{cite journal|title = Structure and energetics of the hydronium hydration shells|author1 = Markovitch, Omer|author2 = Agmon, Noam|journal = [[J. Phys. Chem. A]]|year = 2007|volume = 111|issue = 12|pages = 2253–2256|doi = 10.1021/jp068960g|pmid = 17388314|bibcode = 2007JPCA..111.2253M|url = http://www.fh.huji.ac.il/~agmon/Fullpaper/JPCA111-2253.pdf|archive-url = https://web.archive.org/web/20140813174617/http://www.fh.huji.ac.il/%7Eagmon/Fullpaper/JPCA111-2253.pdf|archive-date = 2014-08-13|citeseerx = 10.1.1.76.9448|access-date = 2017-10-25}}</ref>
-The strength of intermolecular hydrogen bonds is most often evaluated by measurements of equilibria between molecules containing donor and/or acceptor units, most often in solution.<ref>{{cite journal | vauthors = Biedermann F, Schneider HJ | title = Experimental Binding Energies in Supramolecular Complexes | journal = Chemical Reviews | volume = 116 | issue = 9 | pages = 5216–300 | date = May 2016 | pmid = 27136957 | doi = 10.1021/acs.chemrev.5b00583 }}</ref> The strength of intramolecular hydrogen bonds can be studied with equilibria between conformers with and without hydrogen bonds. The most important method for the identification of hydrogen bonds also in complicated molecules is [[crystallography]], sometimes also NMR-spectroscopy. Structural details, in particular distances between donor and acceptor which are smaller than the sum of the van der Waals radii can be taken as indication of the hydrogen bond strength. One scheme gives the following somewhat arbitrary classification: those that are 15 to 40&nbsp;kcal/mol, 5 to 15&nbsp;kcal/mol, and >0 to 5&nbsp;kcal/mol are considered strong, moderate, and weak, respectively.<ref name= Emsley/>
+The strength of intermolecular hydrogen bonds is most often evaluated by measurements of equilibria between molecules containing donor and/or acceptor units, most often in solution.<ref>{{cite journal | vauthors = Biedermann F, Schneider HJ | title = Experimental Binding Energies in Supramolecular Complexes | journal = Chemical Reviews | volume = 116 | issue = 9 | pages = 5216–300 | date = May 2016 | pmid = 27136957 | doi = 10.1021/acs.chemrev.5b00583 }}</ref> The strength of intramolecular hydrogen bonds can be studied with equilibria between conformers with and without hydrogen bonds. The most important method for the identification of hydrogen bonds also in complicated molecules is [[crystallography]], sometimes also NMR-spectroscopy. Structural details, in particular distances between donor and acceptor which are smaller than the sum of the van der Waals radii can be taken as indication of the hydrogen bond strength. One scheme gives the following somewhat arbitrary classification: those that are {{cvt|15|to|40|kcal/mol|order=flip}}, {{cvt|5|to|15|kcal/mol|order=flip}}, and {{cvt|0|to|5|kcal/mol|order=flip}} are considered strong, moderate, and weak, respectively.<ref name= Emsley/>
-Hydrogen bonds involving C-H bonds are both very rare and weak.<ref>{{cite journal |doi=10.1021/ja991795g |title=Fundamental Properties of the CH···O Interaction: Is It a True Hydrogen Bond? |date=1999 |last1=Gu |first1=Yanliang |last2=Kar |first2=Tapas |last3=Scheiner |first3=Steve |journal=Journal of the American Chemical Society |volume=121 |issue=40 |pages=9411–9422 |bibcode=1999JAChS.121.9411G }}</ref>
+Hydrogen bonds involving C−H bonds are both very rare and weak.<ref>{{cite journal |doi=10.1021/ja991795g |title=Fundamental Properties of the CH···O Interaction: Is It a True Hydrogen Bond? |date=1999 |last1=Gu |first1=Yanliang |last2=Kar |first2=Tapas |last3=Scheiner |first3=Steve |journal=Journal of the American Chemical Society |volume=121 |issue=40 |pages=9411–9422 |bibcode=1999JAChS.121.9411G }}</ref>
 ===Resonance assisted hydrogen bond===
-The '''resonance assisted hydrogen bond''' (commonly abbreviated as RAHB) is a strong type of hydrogen bond. It is characterized by the π-delocalization that involves the hydrogen and cannot be properly described by the [[electrostatic]] model alone. This description of the hydrogen bond has been proposed to describe unusually short distances generally observed between {{chem2|O\dC\sOH***}} or {{chem2|***O\dC\sC\dC\sOH}}.<ref>{{cite journal |doi=10.1021/acs.jpca.7b09425 |title=The Origin of the Non-Additivity in Resonance-Assisted Hydrogen Bond Systems |year=2017 |last1=Lin |first1=Xuhui |last2=Zhang |first2=Huaiyu |last3=Jiang |first3=Xiaoyu |last4=Wu |first4=Wei |last5=Mo |first5=Yirong |journal=The Journal of Physical Chemistry A |volume=121 |issue=44 |pages=8535–8541 |pmid=29048895 |bibcode=2017JPCA..121.8535L }}</ref>
+The '''resonance assisted hydrogen bond''' (commonly abbreviated as RAHB) is a strong type of hydrogen bond. It is characterized by the π-delocalization that involves the hydrogen atom and cannot be properly described by the [[electrostatic]] model alone. This description of the hydrogen bond has been proposed to describe unusually short distances generally observed between {{chem2|O\dC\sOH***}} or {{chem2|***O\dC\sC\dC\sOH}}.<ref>{{cite journal |doi=10.1021/acs.jpca.7b09425 |title=The Origin of the Non-Additivity in Resonance-Assisted Hydrogen Bond Systems |year=2017 |last1=Lin |first1=Xuhui |last2=Zhang |first2=Huaiyu |last3=Jiang |first3=Xiaoyu |last4=Wu |first4=Wei |last5=Mo |first5=Yirong |journal=The Journal of Physical Chemistry A |volume=121 |issue=44 |pages=8535–8541 |pmid=29048895 |bibcode=2017JPCA..121.8535L }}</ref>
 ===Structural details===
-The {{chem2|X\sH}} distance is typically ≈110&nbsp;[[picometre|pm]], whereas the {{chem2|H***Y}} distance is ≈160 to 200&nbsp;pm. The typical length of a hydrogen bond in water is 197&nbsp;pm. The ideal bond angle depends on the nature of the hydrogen bond donor. The following hydrogen bond angles between a hydrofluoric acid donor and various acceptors have been determined experimentally:<ref>{{cite journal|doi=10.1039/CS9871600467|title=Angular geometries and other properties of hydrogen-bonded dimers: a simple electrostatic interpretation of the success of the electron-pair model|year=1987|last1=Legon|first1=A. C.|last2=Millen|first2=D. J.|journal=Chemical Society Reviews|volume=16|pages=467}}</ref>
+The {{chem2|X\sH}} distance is typically ≈110&nbsp;[[picometre|pm]], whereas the {{chem2|H***Y}} distance is ≈160 to 200&nbsp;pm. The typical length of a hydrogen bond in water is 197&nbsp;pm. The ideal bond angle depends on the nature of the hydrogen bond donor. The following hydrogen bond angles between a hydrofluoric acid donor and various acceptors have been determined experimentally:<ref>{{cite journal|doi=10.1039/CS9871600467|title=Angular geometries and other properties of hydrogen-bonded dimers: a simple electrostatic interpretation of the success of the electron-pair model|year=1987|last1=Legon|first1=A. C.|last2=Millen|first2=D. J.|journal=Chemical Society Reviews|volume=16|page=467}}</ref>
 {|class="wikitable" style="text-align:left"
 |-
-!{{nowrap|Acceptor···donor}}||VSEPR geometry||Angle (°)
+!{{nowrap|Acceptor···donor}}||VSEPR geometry||Angle
 |-
-|{{chem2|HCN***HF}}||linear||style="text-align:right"|180
+|{{chem2|HCN***HF}}||C≡N···H angle: linear||style="text-align:right"|180°
 |-
-|{{chem2|H2CO***HF}}||trigonal planar||style="text-align:right"|120
+|{{chem2|H2CO***HF}}||C=O···H angle: trigonal planar||style="text-align:right"|120°
 |-
-|{{chem2|H2O***HF}}||pyramidal||style="text-align:right"|46
+|{{chem2|H2O***HF}}||H-O···H angle: pyramidal||style="text-align:right"|46°
 |-
-|{{chem2|H2S***HF}}||pyramidal||style="text-align:right"|89
+|{{chem2|H2S***HF}}||H-S···H angle: pyramidal||style="text-align:right"|89°
 |-
-|{{chem2|SO2***HF}}||trigonal ||style="text-align:right"|145
+|{{chem2|SO2***HF}}||S=O···H angle: trigonal ||style="text-align:right"|145°
 |-
 |}
@@ Line 73: / Line 73: @@
   |volume      = 8
   |issue       = 4
-  |pages       = 1276
+  |page       = 1276
   |doi         = 10.1039/C4EE02280G
   |last1       = Luo
@@ Line 121: / Line 121: @@
 Theoretically, the bond strength of the hydrogen bonds can be assessed using NCI index, [[non-covalent interactions index]], which allows a visualization of these [[non-covalent interactions]], as its name indicates, using the electron density of the system.{{cn|date=June 2023}}
-Interpretations of the [[anisotropy|anisotropies]] in the [[Compton scattering|Compton profile]] of ordinary ice claim that the hydrogen bond is partly covalent.<ref>{{cite journal|last1=Isaacs |first1=E.D.|last2=Shukla|first2=A.|last3=Platzman|first3=P.|last4=Hamann|first4=D.R.|last5=Barbiellini|first5=B.|last6=Tulk|first6=C.A.|journal= Physical Review Letters |doi=10.1103/PhysRevLett.82.600|title=Covalency of the Hydrogen Bond in Ice: A Direct X-Ray Measurement|year=1999|volume=82|issue=3|pages=600–603|bibcode = 1999PhRvL..82..600I}}</ref> However, this interpretation was challenged <ref>{{Cite journal|last1=Ghanty|first1=Tapan K.|last2=Staroverov|first2=Viktor N.|last3=Koren|first3=Patrick R.|last4=Davidson|first4=Ernest R.|date=2000-02-01|title=Is the Hydrogen Bond in Water Dimer and Ice Covalent?|journal=Journal of the American Chemical Society|volume=122|issue=6|pages=1210–1214|doi=10.1021/ja9937019|bibcode=2000JAChS.122.1210G |issn=0002-7863}}</ref> and subsequently clarified. <ref>{{Cite journal|last1=Barbiellini|first1=B.| last2=Shukla|first2=A.|date=2002|title= Ab initio calculations of the hydrogen bond |journal=Physical Review B |volume=66|issue=23|pages=235101|doi=10.1103/PhysRevB.66.235101|arxiv=cond-mat/0210316|bibcode=2002PhRvB..66w5101B }} </ref>
+Interpretations of the [[anisotropy|anisotropies]] in the [[Compton scattering|Compton profile]] of ordinary ice claim that the hydrogen bond is partly covalent.<ref>{{cite journal|last1=Isaacs |first1=E.D.|last2=Shukla|first2=A.|last3=Platzman|first3=P.|last4=Hamann|first4=D.R.|last5=Barbiellini|first5=B.|last6=Tulk|first6=C.A.|journal= Physical Review Letters |doi=10.1103/PhysRevLett.82.600|title=Covalency of the Hydrogen Bond in Ice: A Direct X-Ray Measurement|year=1999|volume=82|issue=3|pages=600–603|bibcode = 1999PhRvL..82..600I}}</ref> However, this interpretation was challenged <ref>{{Cite journal|last1=Ghanty|first1=Tapan K.|last2=Staroverov|first2=Viktor N.|last3=Koren|first3=Patrick R.|last4=Davidson|first4=Ernest R.|date=2000-02-01|title=Is the Hydrogen Bond in Water Dimer and Ice Covalent?|journal=Journal of the American Chemical Society|volume=122|issue=6|pages=1210–1214|doi=10.1021/ja9937019|bibcode=2000JAChS.122.1210G |issn=0002-7863}}</ref> and subsequently clarified.<ref>{{Cite journal|last1=Barbiellini|first1=B.| last2=Shukla|first2=A.|date=2002|title= Ab initio calculations of the hydrogen bond |journal=Physical Review B |volume=66|issue=23|article-number=235101|doi=10.1103/PhysRevB.66.235101|arxiv=cond-mat/0210316|bibcode=2002PhRvB..66w5101B }} </ref>
 Most generally, the hydrogen bond can be viewed as a [[metric (mathematics)|metric]]-dependent [[electrostatic]] [[scalar field]] between two or more intermolecular bonds. This is slightly different from the [[Intramolecular force|intramolecular]] [[bound states]] of, for example, [[covalent bond|covalent]] or [[ionic bond]]s. However, hydrogen bonding is generally still a [[bound state]] phenomenon, since the [[interaction energy]] has a net negative sum. The initial theory of hydrogen bonding proposed by [[Linus Pauling]] suggested that the hydrogen bonds had a partial covalent nature. This interpretation remained controversial until [[nuclear magnetic resonance|NMR techniques]] demonstrated information transfer between hydrogen-bonded nuclei, a feat that would only be possible if the hydrogen bond contained some covalent character.<ref>{{cite journal|title = Observation of through-hydrogen-bond (2h)J(HC') in a perdeuterated protein|journal = [[J Magn Reson]]|year = 1999|volume = 140|pages = 510–2|doi = 10.1006/jmre.1999.1899|pmid = 10497060|issue = 2|bibcode = 1999JMagR.140..510C |last1 = Cordier|first1 = F|last2 = Rogowski|first2 = M|last3 = Grzesiek|first3 = S|last4 = Bax|first4 = A|s2cid = 121429}}</ref>
@@ Line 146: / Line 146: @@
 [[Liquid]] water's high [[boiling point]] is due to the high number of hydrogen bonds each molecule can form, relative to its low [[molecular mass]]. Owing to the difficulty of breaking these bonds, water has a very high boiling point, melting point, and viscosity compared to otherwise similar liquids not conjoined by hydrogen bonds. Water is unique because its oxygen atom has two lone pairs and two hydrogen atoms, meaning that the total number of bonds of a water molecule is up to four.<ref>{{Cite web |date=2017-06-29 |title=11.9: Water - An Extraordinary Substance |url=https://chem.libretexts.org/Courses/Sacramento_City_College/Chem_400%3A_General_Chemistry_I/11%3A_Liquids%2C_Solids%2C_and_Intermolecular_Forces/11.09%3A_Water%3A_An_Extraordinary_Substance |access-date=2024-06-22 |website=Chemistry LibreTexts |language=en}}</ref>
-The number of hydrogen bonds formed by a molecule of liquid water fluctuates with time and temperature.<ref name="Jorgensen1985"/>   From [[water model|TIP4P]] liquid water simulations at 25&nbsp;°C, it was estimated that each water molecule participates in an average of 3.59 hydrogen bonds. At 100&nbsp;°C, this number decreases to 3.24 due to the increased molecular motion and decreased density, while at 0&nbsp;°C, the average number of hydrogen bonds increases to 3.69.<ref name="Jorgensen1985">{{cite journal|author1=Jorgensen, W. L.  |author2=Madura, J. D. |author-link1=William L. Jorgensen|author-link2=Jeffry D. Madura| title=Temperature and size dependence for Monte Carlo simulations of TIP4P water| journal=[[Mol. Phys.]]|year=1985| volume=56 |issue=6 |pages=1381 |doi=10.1080/00268978500103111|bibcode = 1985MolPh..56.1381J }}</ref> Another study found a much smaller number of hydrogen bonds: 2.357 at 25&nbsp;°C.<ref>{{cite journal|author=Zielkiewicz, Jan |title= Structural properties of water: Comparison of the SPC, SPCE, TIP4P, and TIP5P models of water| journal=[[J. Chem. Phys.]]|volume= 123|pages=104501|year=2005| doi=10.1063/1.2018637|pmid=16178604|issue=10|bibcode = 2005JChPh.123j4501Z }}</ref> Defining and counting the hydrogen bonds is not straightforward however.
+The number of hydrogen bonds formed by a molecule of liquid water fluctuates with time and temperature.<ref name="Jorgensen1985"/>   From [[water model|TIP4P]] liquid water simulations at 25&nbsp;°C, it was estimated that each water molecule participates in an average of 3.59 hydrogen bonds. At 100&nbsp;°C, this number decreases to 3.24 due to the increased molecular motion and decreased density, while at 0&nbsp;°C, the average number of hydrogen bonds increases to 3.69.<ref name="Jorgensen1985">{{cite journal|author1=Jorgensen, W. L.  |author2=Madura, J. D. |author-link1=William L. Jorgensen|author-link2=Jeffry D. Madura| title=Temperature and size dependence for Monte Carlo simulations of TIP4P water| journal=[[Mol. Phys.]]|year=1985| volume=56 |issue=6 |page=1381 |doi=10.1080/00268978500103111|bibcode = 1985MolPh..56.1381J }}</ref> Another study found a much smaller number of hydrogen bonds: 2.357 at 25&nbsp;°C.<ref>{{cite journal|author=Zielkiewicz, Jan |title= Structural properties of water: Comparison of the SPC, SPCE, TIP4P, and TIP5P models of water| journal=[[J. Chem. Phys.]]|volume= 123|page=104501|year=2005| doi=10.1063/1.2018637|pmid=16178604|issue=10|bibcode = 2005JChPh.123j4501Z }}</ref> Defining and counting the hydrogen bonds is not straightforward however.
-Because water may form hydrogen bonds with solute proton donors and acceptors, it may competitively inhibit the formation of solute intermolecular or intramolecular hydrogen bonds. Consequently, hydrogen bonds between or within solute molecules dissolved in water are almost always unfavorable relative to hydrogen bonds between water and the donors and acceptors for hydrogen bonds on those solutes.<ref>{{cite journal|author=Jencks, William |title= Hydrogen Bonding between Solutes in Aqueous Solution| journal=[[J. Am. Chem. Soc.]]|volume= 108|pages=4196|year=1986|issue=14|doi=10.1021/ja00274a058|last2=Jencks|first2=William P.|bibcode= 1986JAChS.108.4196S}}</ref> Hydrogen bonds between water molecules have an average lifetime of 10<sup>−11</sup> seconds, or 10 picoseconds.<ref name="Dillon">{{cite book|last=Dillon|first=P. F.|title=Biophysics: A Physiological Approach|url=https://books.google.com/books?id=5IYKLIx-Jt4C|year=2012|publisher=Cambridge University Press|isbn=978-1-139-50462-1|page=37}}</ref>
+Because water may form hydrogen bonds with solute proton donors and acceptors, it may competitively inhibit the formation of solute intermolecular or intramolecular hydrogen bonds. Consequently, hydrogen bonds between or within solute molecules dissolved in water are almost always unfavorable relative to hydrogen bonds between water and the donors and acceptors for hydrogen bonds on those solutes.<ref>{{cite journal|author=Jencks, William |title= Hydrogen Bonding between Solutes in Aqueous Solution| journal=[[J. Am. Chem. Soc.]]|volume= 108|page=4196|year=1986|issue=14|doi=10.1021/ja00274a058|last2=Jencks|first2=William P.|bibcode= 1986JAChS.108.4196S}}</ref> Hydrogen bonds between water molecules have an average lifetime of 10<sup>−11</sup> seconds, or 10 picoseconds.<ref name="Dillon">{{cite book|last=Dillon|first=P. F.|title=Biophysics: A Physiological Approach|url=https://books.google.com/books?id=5IYKLIx-Jt4C|year=2012|publisher=Cambridge University Press|isbn=978-1-139-50462-1|page=37}}</ref>
 === Bifurcated and over-coordinated hydrogen bonds in water ===
 A single hydrogen atom can participate in two hydrogen bonds. This type of bonding is called "bifurcated" (split in two or "two-forked"). It can exist, for instance, in complex organic molecules.<ref>{{cite journal|doi=10.1139/v84-087|journal=Can. J. Chem.|volume= 62|issue= 3|pages= 526–530|title=Hétérocycles à fonction quinone. V. Réaction anormale de la butanedione avec la diamino-1,2 anthraquinone; structure cristalline de la naphto \2,3-f] quinoxalinedione-7,12 obtenue|year=1984|last1=Baron|first1=Michel|last2=Giorgi-Renault|first2=Sylviane|last3=Renault|first3=Jean|last4=Mailliet|first4=Patrick|last5=Carré|first5=Daniel|last6=Etienne|first6=Jean|doi-access=free}}</ref> It has been suggested that a bifurcated hydrogen atom is an essential step in water reorientation.<ref>{{cite journal|title = A Molecular Jump Mechanism for Water Reorientation|author1=Laage, Damien  |author2=Hynes, James T.|journal = [[Science (journal)|Science]]|year = 2006|volume = 311|pages = 832–5|doi = 10.1126/science.1122154|pmid = 16439623|issue = 5762|bibcode = 2006Sci...311..832L |s2cid=6707413 }}</ref>
-Acceptor-type hydrogen bonds (terminating on an oxygen's lone pairs) are more likely to form bifurcation (it is called overcoordinated oxygen, OCO) than are donor-type hydrogen bonds, beginning on the same oxygen's hydrogens.<ref>{{cite journal|title =  The Distribution of Acceptor and Donor Hydrogen-Bonds in Bulk Liquid Water|author1=Markovitch, Omer  |author2=Agmon, Noam |journal = Molecular Physics|year = 2008|volume = 106|issue =  2|pages = 485|doi =  10.1080/00268970701877921|bibcode = 2008MolPh.106..485M |s2cid=17648714 }}</ref>
+Acceptor-type hydrogen bonds (terminating on an oxygen's lone pairs) are more likely to form bifurcation (it is called overcoordinated oxygen, OCO) than are donor-type hydrogen bonds, beginning on the same oxygen atom's hydrogen atoms.<ref>{{cite journal|title =  The Distribution of Acceptor and Donor Hydrogen-Bonds in Bulk Liquid Water|author1=Markovitch, Omer  |author2=Agmon, Noam |journal = Molecular Physics|year = 2008|volume = 106|issue =  2|page = 485|doi =  10.1080/00268970701877921|bibcode = 2008MolPh.106..485M |s2cid=17648714 }}</ref>
 ===Other liquids===
-For example, [[hydrogen fluoride]]—which has three lone pairs on the F atom but only one H atom—can form only two bonds; ([[ammonia]] has the opposite problem: three hydrogen atoms but only one lone pair).
+For example, [[hydrogen fluoride]]—which has three lone pairs on the F atom but only one H atom—can form only two bonds. [[Ammonia]] has the opposite problem: three hydrogen atoms but only one lone pair.
 :<chem>H-F***H-F***H-F</chem>
@@ Line 181: / Line 181: @@
 In the [[Protein secondary structure|secondary structure of proteins]], hydrogen bonds form between the backbone oxygens and [[amide]] hydrogens. When the spacing of the [[amino acid]] residues participating in a hydrogen bond occurs regularly between positions ''i'' and {{nowrap|''i'' + 4}}, an [[alpha helix]] is formed. When the spacing is less, between positions ''i'' and {{nowrap|''i'' + 3}}, then a [[3 10 helix|3<sub>10</sub> helix]] is formed. When two strands are joined by hydrogen bonds involving alternating residues on each participating strand, a [[beta sheet]] is formed. Hydrogen bonds also play a part in forming the [[Protein tertiary structure|tertiary structure of protein]] through interaction of R-groups. (See also [[protein folding]]).{{cn|date=January 2025}}
-[[Bifurcated H-bond]] systems are common in alpha-helical [[transmembrane proteins]] between the backbone amide {{chem2|C\dO}} of residue ''i'' as the H-bond acceptor and two H-bond donors from residue {{nowrap|''i'' + 4}}: the backbone amide {{chem2|N\sH}} and a side-chain hydroxyl or thiol {{chem2|H+}}. The energy preference of the bifurcated H-bond hydroxyl or thiol system is −3.4&nbsp;kcal/mol or −2.6&nbsp;kcal/mol, respectively. This type of bifurcated H-bond provides an intrahelical H-bonding partner for polar side-chains, such as [[serine]], [[threonine]], and [[cysteine]] within the hydrophobic membrane environments.<ref name="Feldblum 2014 4085–4090"/>
+[[Bifurcated H-bond]] systems are common in alpha-helical [[transmembrane proteins]] between the backbone amide {{chem2|C\dO}} of residue ''i'' as the H-bond acceptor and two H-bond donors from residue {{nowrap|''i'' + 4}}: the backbone amide {{chem2|N\sH}} and a side-chain hydroxyl or thiol {{chem2|H+}}. The energy preference of the bifurcated H-bond hydroxyl or thiol system is {{cvt|-3.4|or|40|kcal/mol|order=flip}} respectively. This type of bifurcated H-bond provides an intrahelical H-bonding partner for polar side-chains, such as [[serine]], [[threonine]], and [[cysteine]] within the hydrophobic membrane environments.<ref name="Feldblum 2014 4085–4090"/>
 The role of hydrogen bonds in protein folding has also been linked to osmolyte-induced protein stabilization. Protective osmolytes, such as [[trehalose]] and [[sorbitol]], shift the protein folding equilibrium toward the folded state, in a concentration dependent manner. While the prevalent explanation for osmolyte action relies on excluded volume effects that are entropic in nature, [[circular dichroism]] (CD) experiments have shown osmolyte to act through an enthalpic effect.<ref>{{cite journal|last=Politi|first=Regina|author2=Harries, Daniel|title=Enthalpically driven peptide stabilization by protective osmolytes|journal=ChemComm|year=2010|volume=46|pages=6449–6451|doi=10.1039/C0CC01763A|pmid=20657920|issue=35}}</ref> The molecular mechanism for their role in protein stabilization is still not well established, though several mechanisms have been proposed. Computer [[molecular dynamics]] simulations suggest that osmolytes stabilize proteins by modifying the hydrogen bonds in the protein hydration layer.<ref>{{cite journal|last=Gilman-Politi|first=Regina|author2=Harries, Daniel|title=Unraveling the Molecular Mechanism of Enthalpy Driven Peptide Folding by Polyol Osmolytes|journal=Journal of Chemical Theory and Computation|year=2011|volume=7|issue=11|pages=3816–3828|doi=10.1021/ct200455n|pmid=26598272}}</ref>
@@ Line 189: / Line 189: @@
 A protein backbone hydrogen bond incompletely shielded from water attack is a [[dehydron]]. Dehydrons promote the removal of water through proteins or [[ligand|ligand binding]]. The exogenous dehydration enhances the [[electrostatic]] interaction between the [[amide]] and [[carbonyl]] groups by de-shielding their [[charge (physics)|partial charges]]. Furthermore, the dehydration stabilizes the hydrogen bond by destabilizing the [[nonbonded interactions|nonbonded state]] consisting of dehydrated [[charge (physics)|isolated charges]].<ref>{{cite journal|last=Fernández|first=A.|author2=Rogale K.|author3=Scott Ridgway|author4=Scheraga H. A.|title=Inhibitor design by wrapping packing defects in HIV-1 proteins|journal= Proceedings of the National Academy of Sciences|date=June 2004|volume=101|issue=32|pages=11640–5|pmid=15289598|doi=10.1073/pnas.0404641101|pmc=511032|bibcode=2004PNAS..10111640F|doi-access=free}}</ref>
-[[Wool]], being a protein fibre, is held together by hydrogen bonds, causing wool to recoil when stretched. However, washing at high temperatures can permanently break the hydrogen bonds and a garment may permanently lose its shape.{{cn|date=January 2025}}
+[[Wool]], being a protein fibre, is held together by hydrogen bonds, causing wool to recoil when stretched. However, washing at high temperatures can permanently break the hydrogen bonds and a garment may permanently lose its shape.<ref>{{cite journal |last1=Farnworth |first1=A.J. |title=A Hydrogen Bonding Mechanism for the Permanent Setting of Wool Fibers |journal=Textile Research Journal |date=1957 |volume=27 |issue=8 |pages=632-640 |doi=10.1177/004051755702700807}}</ref>
 ===Other polymers===
@@ Line 204: / Line 204: @@
 ==Application to drugs==
-The Hydrogen bond is relevant to drug design. According to [[Lipinski's rule of five]] the majority of orally active drugs have no more than five hydrogen bond donors and fewer than ten hydrogen bond acceptors. These interactions exist between [[nitrogen]]–[[hydrogen]] and [[oxygen]]–hydrogen centers.<ref name="Lipinski_2004">{{cite journal | author = Lipinski CA | title = Lead- and drug-like compounds: the rule-of-five revolution | journal = Drug Discovery Today: Technologies |date=December 2004 | volume = 1 | issue = 4 | pages = 337–341 | doi = 10.1016/j.ddtec.2004.11.007 | pmid = 24981612 }}</ref> Many drugs do not, however, obey these "rules".<ref>{{cite journal |doi=10.1007/s11306-014-0733-z |title=A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs |year=2015 |last1=o′Hagan |first1=Steve |last2=Swainston |first2=Neil |last3=Handl |first3=Julia |last4=Kell |first4=Douglas B. |journal=Metabolomics |volume=11 |issue=2 |pages=323–339 |pmid=25750602 |pmc=4342520 }}</ref>
+The hydrogen bond is relevant to drug design. According to [[Lipinski's rule of five]] the majority of orally active drugs have no more than five hydrogen bond donors and fewer than ten hydrogen bond acceptors. These interactions exist between [[nitrogen]]–[[hydrogen]] and [[oxygen]]–hydrogen centers.<ref name="Lipinski_2004">{{cite journal | author = Lipinski CA | title = Lead- and drug-like compounds: the rule-of-five revolution | journal = Drug Discovery Today: Technologies |date=December 2004 | volume = 1 | issue = 4 | pages = 337–341 | doi = 10.1016/j.ddtec.2004.11.007 | pmid = 24981612 }}</ref> Many drugs do not, however, obey these "rules".<ref>{{cite journal |doi=10.1007/s11306-014-0733-z |title=A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs |year=2015 |last1=o′Hagan |first1=Steve |last2=Swainston |first2=Neil |last3=Handl |first3=Julia |last4=Kell |first4=Douglas B. |journal=Metabolomics |volume=11 |issue=2 |pages=323–339 |pmid=25750602 |pmc=4342520 }}</ref>
 ==References==

Hydrogen bond: Difference between revisions

Latest revision as of 21:54, 26 May 2026

Contents

Bonding

Definitions and general characteristics

Bond strength

Resonance assisted hydrogen bond

Structural details

Spectroscopy

Theoretical considerations

History

Hydrogen bonds in small molecules

Water

Bifurcated and over-coordinated hydrogen bonds in water

Other liquids

Further manifestations of solvent hydrogen bonding

Hydrogen bonds in polymers

DNA

Proteins

Other polymers

Symmetric hydrogen bond

Dihydrogen bond

Application to drugs

References

Further reading

External links

Navigation menu

Hydrogen bond: Difference between revisions

Latest revision as of 21:54, 26 May 2026

Bonding

Definitions and general characteristics

Bond strength

Resonance assisted hydrogen bond

Structural details

Spectroscopy

Theoretical considerations

History

Hydrogen bonds in small molecules

Water

Bifurcated and over-coordinated hydrogen bonds in water

Other liquids

Further manifestations of solvent hydrogen bonding

Hydrogen bonds in polymers

DNA

Proteins

Other polymers

Symmetric hydrogen bond

Dihydrogen bond

Application to drugs

References

Further reading

External links

Navigation menu

Search