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Related Concept Videos

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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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).
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Molecular Orbital Theory II03:51

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Molecular Orbital Energy Diagrams
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Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

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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.
13.1K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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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...
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π Molecular Orbitals of 1,3-Butadiene01:24

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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...
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MO Theory and Covalent Bonding02:40

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The molecular orbital theory describes the distribution of electrons in molecules in a manner similar to the distribution of electrons in atomic orbitals. The region of space in which a valence electron in a molecule is likely to be found is called a molecular orbital. Mathematically, the linear combination of atomic orbitals (LCAO) generates molecular orbitals. Combinations of in-phase atomic orbital wave functions result in regions with a high probability of electron density, while...
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Benzene Dimer: High-Level Wave Function and Density Functional Theory Calculations.

M Pitoňák1, P Neogrády1, J Rezáč1

  • 1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v. v. i., Flemingovo nám. 2, 166 10 Praha 6, Czech Republic, Department of Physical and Theoretical Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská Dolina, 842 15 Bratislava 4, Slovak Republic, and Department of Physical Chemistry, Palacky University, tr. Svobody 26, 771 46, Olomouc, Czech Republic.

Journal of Chemical Theory and Computation
|December 2, 2015
PubMed
Summary

Accurate calculations reveal the T-shaped tilted (TT) structure is the most stable benzene dimer conformation. This finding, determined via coupled cluster calculations, refines understanding of benzene dimer interactions.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Physical Chemistry

Background:

  • The benzene dimer is a fundamental model system for studying non-covalent interactions.
  • Accurate determination of its potential energy surface is crucial for understanding van der Waals forces and molecular recognition.
  • Previous studies have utilized various theoretical methods, but high-level calculations for key structures are essential.

Purpose of the Study:

  • To perform high-level ab initio calculations for key structures on the benzene dimer potential energy surface.
  • To accurately determine the relative energies of different benzene dimer conformations, including parallel-displaced (PD), T-shaped (T), and T-shaped tilted (TT).
  • To validate a specifically parameterized DFT-D/BLYP method against high-level coupled cluster results.

Main Methods:

  • High-level OVOS CCSD(T) calculations with extrapolation to the complete basis set (CBS) limit.
  • Geometry optimizations using DFT-D/BLYP with a dispersion correction fitted for the benzene dimer system.
  • Estimation of connected quadruple excitations effects using the CCSD(TQf) method.

Main Results:

  • The T-shaped tilted (TT) structure is identified as the most stable conformation, nearly 0.1 kcal/mol lower in energy than the PD and T structures.
  • Connected quadruple excitations slightly destabilize all considered structures, with minor differences between PD, T, and TT.
  • The parameterized DFT-D/BLYP method accurately predicts the energy ordering of the structures, with errors of approximately 0.2 kcal/mol compared to CCSD(T)/CBS.

Conclusions:

  • The TT structure represents the global minimum on the benzene dimer potential energy surface.
  • High-level CCSD(T)/CBS calculations provide benchmark data for the benzene dimer.
  • The specifically parameterized DFT-D/BLYP method offers a reliable and computationally efficient approach for studying benzene dimer interactions.