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Ab initio LCAO ‐ MO ‐ SCF calculation of the electrostatic molecular potential of chlorpromazine and promazine
Author(s) -
Petrongolo Carlo,
Preston Harry J. T.,
Kaufman Joyce J.
Publication year - 1978
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.560130402
Subject(s) - promazine , chemistry , ab initio , phenothiazine , substituent , computational chemistry , linear combination of atomic orbitals , basis set , electrophile , cndo/2 , stereochemistry , molecule , chlorpromazine , density functional theory , organic chemistry , medicine , pharmacology , endocrinology , catalysis
The electrostatic potential V ( r ) arising from the ab initio LCAO‐MO‐SCF wave functions of chlorpromazine ( CPZ ) and promazine ( PZ ) has been calculated and discussed. In this approximation, the most probable sites of attack and reaction paths of electrophilic reagents are pointed out and compared. The analysis of V ( r ) shows that the phenothiazine group has strong nucleophilic properties which are influenced by the phenothiazine substituent and that the electrostatic reactivity of CPZ and PZ is decidedly different near the phenothiazine substituent and similar near the side chain N atom. The dependence of V ( r ) on the accuracy of the wave function has also been discussed by comparing some ab initio results on pyrrole, pyrazole, and imidazole obtained with a large basis set with an ab initio minimum basis set and with CNDO calculations.