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Protonation of aminopyrone: A four centers problem, CNDO /2 versus MNDO study
Author(s) -
Meghezzi H.,
Boucekkine A.,
Kolli B.,
Hamdi M.
Publication year - 1983
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.560240408
Subject(s) - protonation , mndo , cndo/2 , chemistry , nitrogen atom , oxygen atom , atom (system on chip) , computational chemistry , nitrogen , stereochemistry , molecule , ion , organic chemistry , ring (chemistry) , computer science , embedded system
Abstract The mechanism of protonation of aminopyrones and the nature of the protonated forms are of some interest because of the biological importance of these compounds. The use of CNDO/2 molecular electrostatic potentials contour maps shows that the most reactive centre is the extracyclic oxygen. MNDO protonation energies confirm the protonation of this atom and elucidate the basicity of the nitrogen atom. The effect of a N substitution on the basicity of the N 13 atom has been studied. The calculations are in agreement with preliminary experimental results.