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Electrostatic potential mapping of polycyclic aromatic hydrocarbon diol epoxides using a dipole
Author(s) -
Kumar Anil,
Mishra P. C.
Publication year - 1990
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.560380103
Subject(s) - chrysene , mndo , chemistry , diol , epoxide , anthracene , dipole , molecule , polycyclic aromatic hydrocarbon , computational chemistry , hydrocarbon , chemical physics , organic chemistry , photochemistry , catalysis
Electrostatic potential maps of benz(a)anthracene diol epoxide, benzphenanthrene diol epoxide, chrysene diol epoxide, and tryphenylene diol epoxide, which are ultimate carcinogens derived from the corresponding polycyclic aromatic hydrocarbons, have been studied using a dipole of length 1 Å and strength 1 Debye. The net charge distributions in the molecules were obtained using the MNDO molecular orbital method. The maps were drawn for two closest distances of approach between the charged ends of the dipole and atoms of the molecules. Using the electric field directions and values of electrostatic potentials, reactive sites and relative reactivities of these molecules have been examined. Existence of a bay region appears to be important for the carcinogenic activity of a diol epoxide in this class of carcinogens.