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A comparative analysis of the electrostatic potentials of some polycyclic aromatic hydrocarbons
Author(s) -
Politzer Peter,
Daiker Kenneth C.
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560120731
Subject(s) - chrysene , pyrene , chemistry , anthracene , polycyclic aromatic hydrocarbon , carcinogen , computational chemistry , hydrocarbon , phenanthrene , benzo(a)pyrene , molecule , fluoranthene , stereochemistry , environmental chemistry , organic chemistry
Electrostatic potential maps for benzo[a]pyrene, chrysene, 5‐methylchrysene, and 12‐methyl‐benz[a]anthracene are presented and compared. These maps permit an interpretation of the fact that chrysene, a weak carcinogen, becomes as potent as benzo[a]pyrene upon substitution of a methyl group at position 5. It is speculated that a key factor in hydrocarbon carcinogenicity may be the presence of two regions of significant negative potential on opposite sides of the molecule, suitably located with respect to each other.