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Further evaluation and development of charge similarity indices for choosing molecular analogues
Author(s) -
Richard Ann M.,
Rabinowitz James R.
Publication year - 1988
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.560340303
Subject(s) - cndo/2 , ab initio , chemistry , computational chemistry , similarity (geometry) , charge density , charge (physics) , ab initio quantum chemistry methods , molecule , function (biology) , physics , quantum mechanics , computer science , organic chemistry , artificial intelligence , evolutionary biology , image (mathematics) , biology
Two molecular charge similarity index ( CSI ) methods are further evaluated for practical application: one method based on a simple CNDO ‐type approximation to the electron density function and the other based on an ab initio pseudo total charge density function. The test system consists of isosteric analogues of dimethyl ether and methoxy acetic acid. The effects of differences in skeletal structure on the CSI measure of electron density similarity about corresponding atoms is estimated, and two new developments are presented for application of the ab initio‐based method: (1) an INDO ‐type approximation which improves the efficiency of the CSI calculation; and (2) a FOCUS feature which enables comparisons of local molecule regions.