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Structure of Benzene: Molecular Orbital Model

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).

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

Structure of Benzene: Kekulé Model

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Related Experiment Video

Updated: Jun 4, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Benzilic acid: a monoclinic polymorph.

Petrus Prinsloo¹, Eric Cyriel Hosten¹, Richard Betz¹

¹Nelson Mandela University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa.

|December 23, 2024

Summary

This study details the crystal structure of an alpha-hydroxy-carboxylic acid, revealing its molecular arrangement and hydrogen bonding. The compound forms infinite chains through specific intermolecular interactions in its solid state.

Keywords:

benzilic acid crystal structure polymorph

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Published on: October 30, 2018

Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

Previous reports exist on the ortho-rhom-bic polymorph of this alpha-hydroxy-carboxylic acid.
Understanding crystal structures is crucial for predicting material properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C14H12O3.
To identify and describe the intermolecular interactions governing the crystal packing.

Main Methods:

Single-crystal X-ray diffraction analysis.
Analysis of hydrogen bonding and C-H⋯O contacts.

Main Results:

The asymmetric unit contains two complete molecules of the title compound.
The crystal structure is characterized by infinite chains formed along the crystallographic c-axis.
Classical hydrogen bonds and C-H⋯O contacts mediate the chain formation.

Conclusions:

The crystal packing is stabilized by a combination of hydrogen bonds and weaker C-H⋯O interactions.
The identified chain structures provide insights into the solid-state behavior of this alpha-hydroxy-carboxylic acid.