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Hydrogen Bonds

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...

Hydrogen Bonds

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Hydrogen BondsHydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.Hydrogen Bonds Control the World!Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are...

Hybridization of Atomic Orbitals II

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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

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Related Experiment Video

Updated: Jul 11, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Internal Hydrogen Bond Formation in a syn-Hydroxyepoxide.

J P Glusker, D E Zacharias, D L Whalen

Science (New York, N.Y.)

|February 5, 1982

Summary

This summary is machine-generated.

This study confirms an internal hydrogen bond in a syn diol epoxide, a potential carcinogen intermediate. This bond is stable in water solutions and influences molecular structure.

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Published on: September 8, 2013

Area of Science:

Organic Chemistry
Structural Chemistry
Chemical Carcinogenesis

Background:

Polycyclic aromatic hydrocarbons (PAHs) are environmental pollutants.
Metabolism of PAHs can produce diol epoxides, some of which are carcinogenic.
Syn and anti isomers of diol epoxides exhibit different biological activities.

Purpose of the Study:

To investigate the structural characteristics of a syn diol epoxide.
To determine the presence and stability of an internal hydrogen bond in this syn diol epoxide.
To compare the structural features of syn and anti diol epoxides.

Main Methods:

X-ray crystallography was used to determine the solid-state structure.
Nuclear magnetic resonance (NMR) spectroscopy was employed to study the compound in solution.
Solubility studies were conducted in dioxane-water mixtures.

Main Results:

The existence of an internal hydrogen bond was confirmed in 3,4-epoxy-2-methyl-1,2,3,4-tetrahydro-1-naphthol.
This hydrogen bond was found to be stable in aqueous solutions up to 80 mole percent water.
The syn diol epoxide exhibited axial positioning of hydroxyl and methyl groups, contrasting with equatorial positions in the anti isomer.

Conclusions:

The internal hydrogen bond plays a significant role in the conformation of the syn diol epoxide.
The presence of this bond may influence the reactivity and biological activity of the compound.
Structural differences between syn and anti diol epoxides are significant and warrant further investigation.