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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).

Molecular Orbital Theory II

Molecular Orbital Theory II

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π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

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 constants depend...

π Molecular Orbitals of the Allyl Cation and Anion

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...

Predicting Molecular Geometry

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Related Experiment Video

Updated: Jul 4, 2026

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry

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Does an ethene/benzenium ion complex exist? A discrepancy between B3LYP and MP2 predictions.

Stein Kolboe, Stian Svelle

The Journal of Physical Chemistry. A

|July 3, 2008

Summary

Computational chemistry explored the benzenium ion-ethene complex. High-level methods confirmed its existence, requiring 21 kJ/mol for dissociation, validating B3LYP results over MP2 predictions.

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Area of Science:

Computational chemistry
Quantum chemistry
Theoretical chemistry

Background:

Investigating the interaction between the benzenium ion and ethene is crucial for understanding carbocation chemistry.
Previous computational studies yielded conflicting results regarding the stability of this complex.

Discussion:

B3LYP and MP2 computations provided divergent conclusions on the benzenium ion-ethene complex stability.
MP2 suggested the B3LYP-identified structure is unstable, readily forming an ethylbenzenium ion.
Higher-level coupled cluster methods (CCSD, QCISD) corroborated the B3LYP findings.

Key Insights:

The benzenium ion and ethene form a stable complex, contrary to some computational predictions.
A binding energy of 21 kJ/mol was determined for the dissociation of the complex into its constituent ions.
This study resolves computational discrepancies, confirming the existence of the benzenium ion-ethene adduct.

Outlook:

Further theoretical investigations can explore similar interactions with substituted benzenium ions and alkenes.
Experimental validation of this complex could provide deeper insights into reaction mechanisms.
Understanding such non-covalent interactions is vital for predicting reactivity in organic synthesis.