Resonance and aromaticity: an ab initio valence bond approach

The Journal of Physical Chemistry. a
Zahid RashidRemco W A Havenith

Abstract

Resonance energy is one of the criteria to measure aromaticity. The effect of the use of different orbital models is investigated in the calculated resonance energies of cyclic conjugated hydrocarbons within the framework of the ab initio Valence Bond Self-Consistent Field (VBSCF) method. The VB wave function for each system was constructed using a linear combination of the VB structures (spin functions), which closely resemble the Kekulé valence structures, and two types of orbitals, that is, strictly atomic (local) and delocalized atomic (delocal) p-orbitals, were used to describe the π-system. It is found that the Pauling-Wheland's resonance energy with nonorthogonal structures decreases, while the same with orthogonalized structures and the total mean resonance energy (the sum of the weighted off-diagonal contributions in the Hamiltonian matrix of orthogonalized structures) increase when delocal orbitals are used as compared to local p-orbitals. Analysis of the interactions between the different structures of a system shows that the resonance in the 6π electrons conjugated circuits have the largest contributions to the resonance energy. The VBSCF calculations also show that the extra stability of phenanthrene, a kinked benz...Continue Reading

References

Nov 17, 2001·Chemical Reviews·T M Krygowski, M K Cyrański
Nov 17, 2001·Chemical Reviews·L J Schaad, B A Hess
Mar 7, 2002·Journal of the American Chemical Society·Remco W A HavenithLawrence T Scott
May 13, 2003·Chemistry : a European Journal·Chérif F MattaRichard F W Bader
Sep 11, 2003·Chemical Reviews·Milan Randić
Aug 17, 2004·The Journal of Organic Chemistry·Yirong Mo
May 21, 2005·The Journal of Organic Chemistry·Remco W A HavenithLeonardus W Jenneskens
Nov 19, 2005·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mireia GüellMiquel Solà
Dec 13, 2005·Chemistry : a European Journal·Yirong Mo, Paul von Ragué Schleyer
Mar 11, 2006·Chemistry : a European Journal·Jordi PoaterF Matthias Bickelhaupt
Oct 1, 1960·Proceedings of the National Academy of Sciences of the United States of America·E ZuckerkandlL Pauling
Feb 10, 2007·The Journal of Organic Chemistry·Jordi PoaterF Matthias Bickelhaupt
May 24, 2007·The Journal of Physical Chemistry. a·Jordi PoaterMiquel Solà
Mar 28, 2009·The Journal of Physical Chemistry. a·Yirong Mo
Oct 14, 2010·Journal of Computational Chemistry·Zahid Rashid, Joop H van Lenthe
Jul 3, 1996·Journal of the American Chemical Society·Paul von Ragué SchleyerNicolaas J R van Eikema Hommes

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Citations

Jun 17, 2015·Chemical Society Reviews·Kévin CocqRemi Chauvin
Jan 17, 2013·Physical Chemistry Chemical Physics : PCCP·Robert W GóraSławomir J Grabowski
Apr 30, 2014·Physical Chemistry Chemical Physics : PCCP·Thiago Messias CardozoMarco Antonio Chaer Nascimento
Jan 28, 2021·Physical Chemistry Chemical Physics : PCCP·Remco W A HavenithXintao Feng
Mar 4, 2021·Chemical Communications : Chem Comm·Théo P GonçalvesKuo-Wei Huang

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