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Related Concept Videos

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

9.2K
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).
9.2K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

9.1K
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.
9.1K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.4K
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...
8.4K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.7K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
2.7K
Resonance02:52

Resonance

54.5K
The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds. 
54.5K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.6K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
10.6K

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Updated: Jul 15, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-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

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Precise Equilibrium Structure of Benzene.

Brian J Esselman1, Maria A Zdanovskaia1, Andrew N Owen1

  • 1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, United States.

Journal of the American Chemical Society
|September 29, 2023
PubMed
Summary
This summary is machine-generated.

This study precisely determined the equilibrium structure of benzene using advanced computational methods and experimental data. The results show excellent agreement between theoretical and experimental values, establishing new benchmarks for molecular geometry.

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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
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Area of Science:

  • Quantum Chemistry
  • Spectroscopy
  • Molecular Structure Determination

Background:

  • Semi-experimental (rSE) equilibrium structures show excellent agreement with best theoretical estimates (BTEs) for aromatic heterocycles.
  • Previous studies established high accuracy for pyrimidine and pyridazine structures.

Purpose of the Study:

  • Extend the analysis of gas-phase structure determination to the fundamental aromatic molecule, benzene.
  • Achieve highly precise and accurate equilibrium structure (rSE) for benzene.
  • Validate theoretical methods against experimental data for benzene.

Main Methods:

  • Utilized published experimental spectroscopic data from 11 isotopologues of benzene.
  • Applied coupled cluster with singles, doubles, and perturbative triples (CCSD(T)) calculations with large basis sets (cc-pCV5Z).
  • Incorporated corrections for vibration-rotation interaction, electron-mass distribution, finite basis sets, electron correlation, relativistic effects, and Born-Oppenheimer breakdown.

Main Results:

  • Achieved outstanding agreement (0.0001 Å) between rSE and BTE structures for benzene.
  • Determined benzene's D6h geometry with unprecedented precision: R_C-C = 1.3913 (1) Å and R_C-H = 1.0809 (1) Å.
  • Surpassed the agreement levels previously reported for pyrimidine and pyridazine.

Conclusions:

  • The high precision and accuracy of benzene's structure are now established.
  • The excellent agreement between theory and experiment validates both approaches.
  • Discrepancies between semi-experimental and theoretical structures in the literature are substantially resolved.