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Rotation barriers in condensed rings: an extension of Clar's stability rule
Author(s) -
Chuchev Krum,
BelBruno Joseph J.
Publication year - 2006
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1005
Subject(s) - chemistry , benzene , substituent , ring (chemistry) , rotation (mathematics) , computational chemistry , stability (learning theory) , aromaticity , crystallography , stereochemistry , organic chemistry , molecule , geometry , mathematics , machine learning , computer science
The rotation barrier for a substituent OH in systems of condensed benzene rings was studied using density functional theory. The barrier height depends on the position of the hydroxy group and the number of independent benzene rings in the condensed ring system, in agreement with Clar's π‐electron sextet stability model. Investigating OH‐derivatized polycenes with as many as 19 condensed rings showed that increasing the total size of the system does not contribute significantly to the rotation barrier. Copyright © 2005 John Wiley & Sons, Ltd.