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@ARTICLE{Maksic:54979,
author = {Maksic, Z. B. and Baric, D. and Müller, T.},
title = {{C}lar's sextet rule is a consequence of the sigma-electron
framework},
journal = {The journal of physical chemistry / A},
volume = {110},
issn = {1089-5639},
address = {Washington, DC},
publisher = {Soc.},
reportid = {PreJuSER-54979},
pages = {10135 - 10147},
year = {2006},
note = {Record converted from VDB: 12.11.2012},
abstract = {A number of condensed PAHs are examined to identify the
underlying reasons governing empirical Clar's rule taking
benzene as a limiting case. It is found that the so-called
Clar's structures are the only minima on the MP2(fc)
potential energy hypersurfaces, meaning that other
conceivable valence isomers are nonexistent. The influence
of the electron correlation energies to the stability of
Clar's structures is substantial with predominating
influence of the sigma-electrons. However, the contributions
arising from the sigma- and pi-electron correlation energies
are approximately the same, if Clar's structures are
compared with some artificial pi-electron localized or
graphite-like delocalized planar systems. Analysis of the
Hartree-Fock (HF) energies provides a compelling evidence
that the origin of stability of Clar's structures lies in a
decrease of the positive T, V(ee) and V(nn) energy terms
relative to some characteristic virtual "delocalized" or
"localized" model geometries. Partitioning of the mixed and
terms in the sigma- and pi-type contributions, by using the
stockholder (SHR), equipartitioning (EQP) and standard pi
(SPI) schemes, unequivocally shows that the driving force
leading to Clar's structures are more favorable sigma-type
interactions. All these conclusions hold for the archetypal
benzene too, which could be considered as a limiting Clar
system. Finally, the boundaries of Clar's hypothesis and
some common misconceptions are briefly discussed. Perusal of
the geometric parameters and pi-bond orders reveals that
there are no benzene rings completely "vacant" or "fully
occupied" by the pi-electrons, envisaged by Clar in his
picture of condensed benzenoid compounds. Instead, there are
six-membered rings with higher and lower total pi-electron
density. The bond length anisotropy of the former rings is
smaller. It is concluded that Clar's proposition is a useful
rule of thumb providing qualitative information on the
stability of the PAH systems, which in turn should not be
overinterpreted.},
keywords = {J (WoSType)},
cin = {ZAM},
ddc = {530},
cid = {I:(DE-Juel1)VDB62},
pnm = {Scientific Computing},
pid = {G:(DE-Juel1)FUEK411},
shelfmark = {Chemistry, Physical / Physics, Atomic, Molecular $\&$
Chemical},
typ = {PUB:(DE-HGF)16},
pubmed = {pmid:16913689},
UT = {WOS:000239817900021},
doi = {10.1021/jp062917b},
url = {https://juser.fz-juelich.de/record/54979},
}