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Intermolecular attraction between a hydrogen donor-and-acceptor pair
In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as
Hydrogen_bond
Covalent chemical bond between hydrogen and carbon atoms
the carbon–hydrogen bond (C−H bond) is a chemical bond between carbon and hydrogen atoms that can be found in many organic compounds. This bond is a covalent
Carbon–hydrogen_bond
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
Symmetric_hydrogen_bond
Quantum chemical model of molecular and condensed matter electronic systems
two ortho hydrogen atoms again is shorter than their van der Waals radii, and according to in silico experiments based on this theory, a bond path is identified
Atoms_in_molecules
Type of organocatalysis
Hydrogen-bond catalysis is a type of organocatalysis that relies on use of hydrogen bonding interactions to accelerate and control organic reactions.
Hydrogen-bond_catalysis
Chemical element with atomic number 1 (H)
hydrogen is a gas of diatomic molecules with the formula H2, called dihydrogen, or sometimes hydrogen gas, molecular hydrogen, or simply hydrogen. Dihydrogen
Hydrogen
Physical and chemical properties of pure water
dissociate ions in salts and bond to other polar substances such as alcohols and acids, thus dissolving them. Their hydrogen bonding causes their many unique
Properties_of_water
Force of attraction or repulsion between molecules and neighboring particles
categorized into the following types: Hydrogen bonding Ion–dipole forces and ion–induced dipole force Cation–π, σ–π and π–π bonding Van der Waals forces – Keesom
Intermolecular_force
Chemical bond by sharing of electron pairs
valence bond theory. In the molecule H 2, the hydrogen atoms share the two electrons via covalent bonding. The covalent character of a bond, as opposed
Covalent_bond
Association of atoms to form chemical compounds
single bond between two atoms corresponds to the sharing of one pair of electrons. The Hydrogen (H) atom has one valence electron. Two Hydrogen atoms can
Chemical_bond
Chemical compound
coloration. The molecule hydrogen peroxide is asymmetrical and highly polarized. Its strong tendency to form hydrogen bond networks results in greater
Hydrogen_peroxide
Protein structural motif
can be defined in two ways: By the possession of an intra-main-chain hydrogen bond between the CO of residue i and the NH of residue i+3; By having a distance
Beta_turn
Chemical compound
internal hydrogen bond is formed between the groups. The hydroxy group serves here as the hydrogen bond donor, and the aldehyde as hydrogen bond acceptor
Salicylaldehyde
Rule of thumb to predict if a chemical compound is likely to be an orally active drug
criteria: No more than 5 hydrogen bond donors (the total number of nitrogen–hydrogen and oxygen–hydrogen bonds) No more than 10 hydrogen bond acceptors (all nitrogen
Lipinski's_rule_of_five
American scientist
17, 1981) was a scientist who independently conceived the idea of hydrogen bonding and who was an early advocate for their role in stabilizing protein
Maurice_Loyal_Huggins
Protein structure classification tool
carbonyl oxygen and amide hydrogen respectively, their opposites assigned to the carbonyl carbon and amide nitrogen. A hydrogen bond is identified if E in
DSSP_(algorithm)
Chemical compound
strong and extensive hydrogen bonding, it boils near room temperature, a much higher temperature than other hydrogen halides. Hydrogen fluoride is an extremely
Hydrogen_fluoride
Base pairs in molecular genetics
Non-canonical base pairs are planar, hydrogen-bonded pairs of nucleobases with hydrogen-bonding patterns that differ from those of standard Watson–Crick
Non-canonical_base_pairing
A Low-barrier hydrogen bond (LBHB) is a special type of hydrogen bond. LBHBs can occur when the pKa of the two heteroatoms are closely matched, which
Low-barrier_hydrogen_bond
Use of squaramides as hydrogen-bond catalyst to accelerate reactions
through hydrogen-bonding interactions between the substrate and the squaramide, unlike classic catalysts, and is thus a type of hydrogen-bond catalyst
Squaramide_catalysis
Quantum mechanical phenomenon
associated with hydrogen bonds. In many molecules that contain hydrogen, the hydrogen atoms are linked to two non-hydrogen atoms via a hydrogen bond at one end
Proton_tunneling
Chemical bond which does not involve the sharing of electrons
(Na+). A hydrogen bond (H-bond), is a specific type of interaction that involves dipole–dipole attraction between a partially positive hydrogen atom and
Non-covalent_interaction
Protein structural motif
proposed by William Astbury in the 1930s. He proposed the idea of hydrogen bonding between the peptide bonds of parallel or antiparallel extended β-strands
Beta_sheet
Net attractive interaction involving one of the halogen elements
another, or the same, molecular entity. Like a hydrogen bond, the result is not a formal chemical bond, but rather a strong electrostatic attraction.
Halogen_bond
Separation of electric charge in a molecule
polarity if the bond dipoles cancel each other out by symmetry. Polar molecules interact through dipole-dipole intermolecular forces and hydrogen bonds. Polarity
Chemical_polarity
Organic reaction
carbon–hydrogen bond activation (C−H activation) is a type of organic reaction in which a carbon–hydrogen bond is cleaved and replaced with a C−X bond (X
Carbon–hydrogen bond activation
Carbon–hydrogen_bond_activation
Two water molecules held together by a hydrogen bond; the simplest water cluster
loosely bound by a hydrogen bond. It is the smallest water cluster. Because it is the simplest model system for studying hydrogen bonding in water, it has
Water_dimer
Two nucleobases bound by hydrogen bonds
to the folded structure of both DNA and RNA. Dictated by specific hydrogen bonding patterns, "Watson–Crick" (or "Watson–Crick–Franklin") base pairs (guanine–cytosine
Base_pair
Covalent bond between amino acids in a protein chain
placing the peptide group in a hydrophobic environment or donating a hydrogen bond to the nitrogen atom of an X-Pro peptide group. Both of these mechanisms
Peptide_bond
Cluster of water molecules held together through hydrogen bonding
experimentally. One line of research uses graph invariants for generating hydrogen bond topologies and predicting physical properties of water clusters and
Water_cluster
General three-dimensional form of local segments of proteins
helix and π helix, are calculated to have energetically favorable hydrogen-bonding patterns but are rarely observed in natural proteins except at the
Protein_secondary_structure
Mixing (superposition) of atomic orbitals
two bonds is the tetrahedral bond angle of 109°28' (around 109.5°). Pauling supposed that in the presence of four hydrogen atoms, the s and p orbitals
Orbital_hybridisation
Solutions of Lewis or Brønsted acids and bases
The parent components of deep eutectic solvents engage in a complex hydrogen bonding network, which results in significant freezing point depression as
Deep_eutectic_solvent
Representation method in chemistry
a single group (e.g., OH, NH2) without explicitly showing the hydrogen–heteroatom bond. Heteroatoms with simple alkyl or aryl substituents, like methoxy
Skeletal_formula
Loss of structure in proteins and nucleic acids due to external stress
in hydrogen bonding. These molecules compete with surrounding hydrogen bond acceptors for hydrogen bond donors, therefore acting as "hydrogen bond breakers"
Denaturation_(biochemistry)
Association of molecules of a solvent with molecules or ions of a solute
and solute molecules into solvation complexes and involves bond formation, hydrogen bonding, and van der Waals forces. Solvation of a solute by water is
Solvation
are diverse hydrogen bonding pair choices that could be used in HOFs construction, including identical or nonidentical hydrogen bonding donors and acceptors
Hydrogen-bonded organic framework
Hydrogen-bonded_organic_framework
Type of secondary structure of proteins
with 13 atoms being involved in the ring formed by the hydrogen bond (starting with amidic hydrogen and ending with carbonyl oxygen) In the early 1930s,
Alpha_helix
Chemical process
non-covalent interactions, especially hydrogen bonding ("partial protonation"). The scope of these small-molecule H-bond donors termed (thio)urea organocatalysis
Thiourea_organocatalysis
Interactions between groups of atoms that do not arise from chemical bonds
solubility. Van der Waals forces are also responsible for the weak hydrogen bond interactions between unpolarized dipoles particularly in acid-base aqueous
Van_der_Waals_force
Chemical compound of hydrogen and oxygen
solvent. Water, being a polar molecule, undergoes strong intermolecular hydrogen bonding which is a large contributor to its physical and chemical properties
Water
Solid consisting of discrete molecules
interactions, quadrupole interactions, π–π interactions, hydrogen bonding, halogen bonding, London dispersion forces, and in some molecular solids, coulombic
Molecular_solid
Strength of a chemical bond
molecule, the bond-dissociation energy of an oxygen–hydrogen bond varies slightly depending on whether or not there is another hydrogen atom bonded to
Bond_energy
Approximate quantum chemistry model
are the screening charge densities of the hydrogen bond acceptor and donor respectively. The hydrogen bonding threshold σhb and the prefactor chb are adjustable
COSMO-RS
Compound derived from an acid
polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols.
Ester
Organic compounds of the form >C=O
are not usually hydrogen-bond donors and cannot hydrogen-bond to themselves. Because of their inability to serve both as hydrogen-bond donors and acceptors
Ketone
Chemical compound
atom). The hydrogen bonds form at two sites: as a donor at a tyrosine residue and as an acceptor at an arginine residue. Whilst the hydrogen bond accepting
Cyclopamine
Chemical compound
formula HCl. Hydrogen chloride is a diatomic molecule, consisting of a hydrogen atom H and a chlorine atom Cl connected by a polar covalent bond. The chlorine
Hydrogen_chloride
In chemistry, a dihydrogen bond is a kind of hydrogen bond, an interaction between a metal hydride bond and an OH or NH group or other proton donor. With
Dihydrogen_bond
Protons hopping across hydrogen bonds between hydronium ions and water molecules
which an 'excess' proton diffuses through the hydrogen bond network of water molecules or other hydrogen-bonded liquids through the formation and concomitant
Grotthuss_mechanism
States of matter for water as a solid
close to the angle between hydrogen atoms in the water molecule (in the gas phase), which is 105°. This tetrahedral bonding angle of the water molecule
Phases_of_ice
Process in homeopathy
solutions of sodium chloride and lithium chloride have a very different hydrogen bond structure from normal water, as measured by thermoluminescence. Not
Homeopathic_dilutions
C–H···O interaction is occasionally described as a special type of weak hydrogen bond. These interactions frequently occur in the structures of important
C–H···O_interaction
Polymeric arrays of repeating units connected by non-covalent bonds
Waals interactions, hydrogen bonding, Coulomb or ionic interactions, π-π stacking, metal coordination, halogen bonding, chalcogen bonding, and host–guest
Supramolecular_polymer
Tendency of some substituents on a cyclohexane ring to prefer axial orientation
energetically favourable hydrogen bond between the axial H-5 and a lone pair of electrons on the axial α-anomeric substituent (C–H/n hydrogen bond), have been suggested
Anomeric_effect
Chemical compound of DNA and RNA
three hydrogen bonds. In cytosine, the amino group acts as the hydrogen bond donor and the C-2 carbonyl and the N-3 amine as the hydrogen-bond acceptors
Guanine
Self-healing polymer material
would depend on covalent bonding and ionic bonding between chains, which is typical of normal rubber. In this case hydrogen bonding can occur simply by pressing
Smart_rubber
Molecules that disrupt hydrogen bonding
chaotropic agent is a molecule in water solution that can disrupt the hydrogen bonding network between water molecules (i.e. exerts chaotropic activity).
Chaotropic_agent
Enzyme family
an extensive hydrogen bonding network, including residues Arg34, which hydrogen bonds to the nicotinamide group, Arg170, which hydrogen bonds to the 2'-phosphate
5α-Reductase
Chemical compound
structure of the active drug Ibandronate: its molecular weight, hydrogen bond acceptors, hydrogen bond donors, and its clogP value. Generally, a medication is
Ibandronic_acid
Simplest carboxylic acid (HCOOH)
hydrogen tetrafluoroborate in anhydrous hydrogen fluoride). The difference has been ascribed to a transition state stabilized by hydrogen bonding with
Formic_acid
Ion with formula HF2 and charge 1-
by a 3-center 4-electron bond (symmetrical hydrogen bond), in a sort of hybrid between a hydrogen bond and a covalent bond. Salts, such as potassium
Bifluoride
Relation between temperature and the equilibrium constant of a chemical reaction
enthalpically, the water preferred to hydrogen bond to the C-terminus, but entropically it was more favorable to hydrogen bond with the N-terminus. Specifically
Van_'t_Hoff_equation
Organic compounds of the form RC(=O)NR′R″
participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate
Amide
Type of strain energy in organic chemistry
to put a much smaller hydrogen in the hydrogen bond acceptor’s position, it is much more favorable to allow the hydrogen bond to form. Solvents also
Allylic_strain
Tendency of gold complexes to aggregate
aurophilic bond has a length of about 3.0 Å and a strength of about 7–12 kcal/mol, which is comparable to the strength of a hydrogen bond. The effect
Aurophilicity
Substance composed of multiple chemically bonded elements
"Gold Book") (2025). Online version: (2006–) "hydrogen bond". doi:10.1351/goldbook.H02899 "Hydrogen Bonding". www.chem.purdue.edu. Archived from the original
Chemical_compound
Covalent bond between carbon and fluorine atoms
bond dissociation energy (BDE) of up to 130 kcal/mol. The BDE (strength of the bond) of C–F is higher than other carbon–halogen and carbon–hydrogen bonds
Carbon–fluorine_bond
Chemical compound
cellobiose octaacetate, of which there is no longer a hydrogen bond donor (though it is still a hydrogen bond acceptor) and possesses aspects of being soluble
Cellobiose
Three-dimensional arrangement of atoms in an amino acid-chain molecule
conformations driven by a number of non-covalent interactions, such as hydrogen bonding, ionic interactions, Van der Waals forces, and hydrophobic packing
Protein_structure
Compounds containing hydrogen
lone pair, a phenomenon called hydrogen bonding that is critical to the stability of many biological molecules. Hydrogen also forms compounds with less
Hydrogen_compounds
One of the lightest perfluoro compounds
electron-withdrawing nature of the trifluoromethyl group weakens the oxygen–hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate
Trifluoroacetic_acid
Type of hydrogel
attraction forces drive new bond formation through reconstructive covalent dangling side chain or non-covalent hydrogen bonding. These flesh-like properties
Self-healing_hydrogels
Chemical information database
structure, name fragments, chemical formula, molecular weight, XLogP, and hydrogen bond donor and acceptor count. PubChem contains its own online molecule editor
PubChem
British and American chemist (born 1948)
hydrogen bonding that involves metal hydrides, resulting in unconventional bonding interactions. Traditional hydrogen bonds feature a protic hydrogen
Robert_H._Crabtree
Abstract description of molecular features
pharmacophore features include hydrophobic centroids, aromatic rings, hydrogen bond acceptors or donors, cations, and anions. These pharmacophore points
Pharmacophore
Covalent bond between two carbon atoms
strongly electron-withdrawing iodonium moiety. Carbon–hydrogen bond Carbon–oxygen bond Carbon–nitrogen bond Dembicki, Harry (2016-10-06). Practical Petroleum
Carbon–carbon_bond
State of matter
Michele; Manolopoulos, David E. (2013-09-06). "Nuclear quantum effects and hydrogen bond fluctuations in water". Proceedings of the National Academy of Sciences
Liquid
Design method for proteins
Yun-Wei (2021). "Protein Stability Depends Critically on the Surface Hydrogen-Bonding Network: A Case Study of Bid Protein". The Journal of Physical Chemistry
QTY_Code
absorption bands are affected by hydrogen bonding. In crystalline ice the vibrational spectrum is also affected by hydrogen bonding and there are lattice vibrations
Electromagnetic absorption by water
Electromagnetic_absorption_by_water
Chemical compound (OH–)
chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an
Hydroxide
Branch of chemistry
weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains
Supramolecular_chemistry
Three-dimensional shape of a nucleic acid polymer
inserted base. This allows for optimal van der Waals contacts, extensive hydrogen bonding and hydrophobic surface burial, and creates a highly energetically
Nucleic acid tertiary structure
Nucleic_acid_tertiary_structure
Most abundant structural protein in animals
association of the collagen fibers within the molecule, facilitating hydrogen bonding and the formation of intermolecular cross-links. This kind of regular
Collagen
Chemical compound
Exploiting their rigid planar structures, these compounds are of interest as hydrogen-bond donors in supramolecular chemistry and squaramide catalysis. Squaramides
Squaramide
hydrogen bonding interactions. Bifurcated hydrogen bonds and multiple hydrogen bonds between amino acid residues; and intra- and interchain hydrogen bonds
Protein_contact_map
Esters of phosphoric acid with a chiral backbone
compounds are used in asymmetric catalysis as chiral Brønsted acids and/or hydrogen-bond donors. The conjugate bases are also used in generating chiral ion pairs
Chiral_phosphoric_acid
Protein family
C-terminal carboxylate through hydrogen bonding: Salt linkage with positively charged Arg-145 Hydrogen bond from Tyr-248 Hydrogen bond from the nitrogen of the
Carboxypeptidase_A
Bonding of atoms of the same element into chains or rings
including hydrogen, boron, silicon, phosphorus, sulfur and halogens. The ability of an element to catenate is primarily based on the bond energy of the
Catenation
Natural phenomenon that hot water freezes faster than cold
Yichun; Zhou, Ji; Zheng, Weitao; Jiange, Qing; Sun, Chang Q. (2014). "Hydrogen-bond memory and water-skin supersolidity resolving the Mpemba paradox". Physical
Mpemba_effect
Type of parameter
Critical compilation of scales of solvent parameters. part I. pure, non-hydrogen bond donor solvents – technical report. Pure Appl. Chem. 71(4), 645–718 (IUPAC
Hildebrand solubility parameter
Hildebrand_solubility_parameter
Substance dissolving a solute resulting in a solution
respective chemical properties of the solvent and solute, such as hydrogen bonding, dipole moment and polarizability. Solvation does not cause a chemical
Solvent
Chemical compound
causing the strength of the hydrogen bond to increase as well. Protonation of the adenine increases the strength of the hydrogen bonds. The presence of water
Deoxyadenosine_monophosphate
Phyllosilicate clay mineral
clay is dried, most of the water molecules are removed, and the plates hydrogen bond directly to each other, so that the dried clay is rigid but still fragile
Kaolinite
Greek-American chemist
organometallic catalysis focuses on developing highly selective carbon–hydrogen bond activation methods to streamline the process of complex molecule synthesis
M._Christina_White
Mammalian protein found in humans
also hydrogen bonds to substrate 6-OH. The 3'-OH of the substrate ribose forms a hydrogen bond with Asp19, while the 5'-OH forms a hydrogen bond with
Adenosine_deaminase
quite acidic. The hydrogen atom is directly bounded to the metal. The metal-hydrogen bond length is for cobalt 114 pm, the metal-carbon bond length is for
Metal_carbonyl_hydride
Type of coupling used in NMR spectroscopy
active nuclei on both sides of the hydrogen bond. Initially, it was surprising to observe such couplings across hydrogen bonds since J-couplings are usually
J-coupling
Crystallographic defect affecting the electrical properties of ice
electrical polarization of ice in an electric field. A hydrogen bond normally has one proton, but a hydrogen bond with a Bjerrum defect will have either two protons
Bjerrum_defect
non-endcapped columns. Endcapped columns show decreased retention for hydrogen bond acceptors, such as ionized bases, and increased retention for protonated
Endcapping
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