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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).

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

Hybridization of Atomic Orbitals II

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...

π Molecular Orbitals of 1,3-Butadiene

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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...

Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...

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Related Experiment Video

Updated: Dec 30, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

Is There BN Bond-Length Alternation in 1,2:3,4:5,6-Tris(biphenylylene)borazines?

Matthias Müller¹, Cäcilia Maichle-Mössmer², Peter Sirsch²

¹Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen (Germany).

|January 29, 2020

Summary

Computational methods reveal minimal bond length alternation in tris(biphenylylene)borazine derivatives. This study clarifies B-N bond characteristics in these unique aromatic borazine structures.

Keywords:

borazine density functional calculations electrophilic substitution isoelectronic analogues structure elucidation

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

Area of Science:

Computational Chemistry
Materials Science
Organic Chemistry

Background:

Borazine rings, particularly in overcrowded structures like tris(biphenylylene)borazine, exhibit unique electronic properties.
Understanding the B-N bond alternation is crucial for predicting molecular geometry and reactivity.
Previous experimental data on bond length alternation (BLA) in these systems showed discrepancies.

Purpose of the Study:

To computationally investigate the B-N bond alternation in 1,2:3,4:5,6-tris(biphenylylene)borazine (2a) and its tribromo derivative (2g).
To compare computational findings with experimental crystal structure data.
To elucidate the structural characteristics of these overcrowded borazines.

Main Methods:

Density functional theory (DFT) calculations using the meta-GGA functional TPSS.
Inclusion of dispersion corrections with Becke-Johnson damping.
Utilized a polarized triple-zeta basis set for accurate electronic structure determination.

Main Results:

Calculations predict a small B-N bond length alternation (BLA) of approximately 0.01 Å for both 2a and 2g.
Computational results align well with X-ray diffraction data for the tribromo derivative (2g).
Re-examination of crystal structure for 2a indicated positional disorder, preventing definitive B-N bond length analysis.

Conclusions:

Computational modeling accurately describes the B-N bond alternation in the studied aryl borazines.
The synthesis of 2g represents the first successful electrophilic aromatic substitution on an aryl borazine using elemental bromine.
Bromination was also achieved for hexaphenylborazine, broadening the scope of aryl borazine functionalization.