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An ab initio study of the proton affinities of some heteroatomic rings: Imidazole, oxazole, and thiazole
Author(s) -
Kabir Shahrzad,
Sapse AnneMarie
Publication year - 1991
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540120913
Subject(s) - oxazole , affinities , thiazole , imidazole , chemistry , substituent , proton affinity , ab initio , ab initio quantum chemistry methods , proton , computational chemistry , stereochemistry , organic chemistry , molecule , physics , ion , protonation , quantum mechanics
The proton affinities of imidazole, oxazole, and thiazole rings, relevant to the binding of lexitropsins that contain these rings to the minor groove of DNA, are calculated using ab initio (Hartree–Fock) calculations. It is found that the proton affinities decrease in the order imidazole, oxazole, thiazole and that a methyl group substituent increases the proton affinity of imidazole, while a peptidic group decreases it.