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Related Concept Videos

Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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...
NMR Spectroscopy of Benzene Derivatives01:37

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 constants depend...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

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).
Structure of Benzene: Kekulé Model01:07

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.
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).
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the more strongly...

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Related Experiment Video

Updated: Jul 6, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-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

Conformations of substituted benzophenones.

Philip J Cox1, Dimitrios Kechagias, Orla Kelly

  • 1The Robert Gordon University, Schoolhill, Aberdeen AB10 1FR, Scotland. p.j.cox@rgu.ac.uk

Acta Crystallographica. Section B, Structural Science
|March 29, 2008
PubMed
Summary

This study examines aryl ring twists in benzophenone molecules, revealing how steric and crystal packing forces influence dihedral angles. A new derivative exhibits the smallest twist angle reported to date, offering insights into molecular conformation.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

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Last Updated: Jul 6, 2026

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

Published on: December 16, 2019

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Benzophenone derivatives are crucial in various chemical applications.
  • Understanding the conformational flexibility of benzophenones is key to predicting their properties.
  • Aryl ring inclination (ring twist) is influenced by intramolecular steric effects and intermolecular crystal packing forces.

Purpose of the Study:

  • To investigate the dihedral angles between aryl rings in a series of substituted benzophenone molecules.
  • To correlate observed ring twists with steric factors and crystal packing.
  • To identify novel benzophenone structures with unique conformational properties.

Main Methods:

  • X-ray crystallography was employed to determine the precise three-dimensional structures of six new benzophenone derivatives.
  • Dihedral angles were measured to quantify the 'ring twist' between the two aryl rings.
  • Comparisons were made with existing data for 98 other substituted benzophenones from the Cambridge Structural Database (CSD).

Main Results:

  • A new compound, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, exhibits the smallest reported twist angle (37.85°) for a substituted benzophenone.
  • Several other substituted benzophenones showed ring twists ranging from approximately 50° to 52°, similar to unsubstituted benzophenone.
  • A 4-chloro-4'-hydroxybenzophenone derivative displayed a larger twist angle (64.66°), while a dichlorinated derivative showed a significant twist of 83.72°.

Conclusions:

  • The study successfully quantified the ring twist in various substituted benzophenones.
  • Both steric hindrance within the molecule and crystal packing forces significantly dictate the observed dihedral angles.
  • The identification of a benzophenone with an exceptionally small twist angle opens avenues for further research into structure-property relationships.