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Related Concept Videos

Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
Hydrogen Bonds01:04

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 Bonds00:26

Hydrogen Bonds

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...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

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Related Experiment Video

Updated: Jul 12, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Benzene forms hydrogen bonds with water.

S Suzuki, P G Green, R E Bumgarner

    Science (New York, N.Y.)
    |August 14, 1992
    PubMed
    Summary

    Benzene-water clusters reveal water

    Area of Science:

    • Physical Chemistry
    • Molecular Spectroscopy
    • Computational Chemistry

    Background:

    • Understanding intermolecular forces is crucial in chemistry.
    • Aqueous-pi electron interactions are fundamental in many chemical and biological processes.
    • Benzene and water are ubiquitous molecules, and their interaction serves as a model system.

    Purpose of the Study:

    • To experimentally and theoretically investigate the structure and binding of benzene-water clusters.
    • To elucidate the nature of hydrogen bonding between water and the pi system of benzene.

    Main Methods:

    • High-resolution rotational spectroscopy was used to determine the moments of inertia of benzene-water isotopologues.
    • Ab initio calculations at the MP2 level with a 6-31 G(**) basis set were performed.

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    Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

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    Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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    Synthesis and Characterization of Supramolecular Colloids

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    Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
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  • Basis set superposition error corrections were applied to theoretical calculations.

    • Main Results:

    • Spectroscopic analysis confirmed water is positioned above the benzene plane with internal rotation.
    • Both hydrogen atoms of water point towards the benzene pi cloud.
    • Calculations predicted a binding energy of approximately 1.78 kcal/mol.
    • Experimental and theoretical structures showed water is significantly closer to benzene than van der Waals contacts suggest, indicating hydrogen bond formation.

    Conclusions:

    • The study provides unambiguous evidence for hydrogen bond formation in benzene-water clusters.
    • The results offer a detailed model for aqueous-pi electron interactions.
    • This research enhances understanding of non-covalent interactions in molecular systems.