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Quantum molecular study of the alkylating agent mechlorethamine
Author(s) -
Broch H.,
Viani R.,
Vasilescu D.
Publication year - 1991
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.560400715
Subject(s) - chemistry , computational chemistry , carbonium ion , ab initio , nitrogen mustard , molecular dynamics , macromolecule , cndo/2 , molecule , stereochemistry , organic chemistry , biochemistry , catalysis , medicine , surgery , chemotherapy , cyclophosphamide
Mechlorethamine HN2 is a nitrogen mustard that is recognized as a fundamental model for the alkylating agents belonging to this family. This molecule is an anticancer drug that reacts strongly with intracellular DNA through a complex electrostatic mechanism. An ab initio quantum molecular study of three molecular models (neutral HN2, quaternized HN2 + aziridinium, and HN2 + free carbonium) is presented in this work. The Conformations and the Mulliken charge distributions were obtained by using HF / STO ‐3G, HF /6–31G*, and HF /6–31G computations. Conformational aspects and electrostatic properties are discussed with respect to the mechanism of alkylation.