title: Hydrolysis of a chlorambucil analogue. A DFT study.
abstract: We study by density functional theory the hydrolysis of a chlorambucil analogue. Three SN(1) and one SN(2) mechanisms have been compared. Results show that the most likely mechanism involves the formation of an aziridinium ion via a first-order reaction subject to an energy barrier of 24.8 kcal/mol. Additionally, a kinetic study, using the thermodynamic formulation of the Transition State Theory, has been carried out. Theoretical results coincide with experimental values obtained under similar conditions of pH, temperature and chloride concentration.
authors.affiliation: Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Edificio 179, 18 Sur y Av. San Claudio, Col. San Manuel, 72570 Puebla, Puebla, México.
authors.forename: F P
authors.initials: FP
authors.lastname: Pineda
authors.forename: J
authors.initials: J
authors.lastname: Ortega-Castro
authors.forename: J R
authors.initials: JR
authors.lastname: Alvarez-Idaboy
authors.forename: J
authors.initials: J
authors.lastname: Frau
authors.forename: B M
authors.initials: BM
authors.lastname: Cabrera
authors.forename: J C
authors.initials: JC
authors.lastname: Ramírez
authors.forename: J
authors.initials: J
authors.lastname: Donoso
authors.forename: F
authors.initials: F
authors.lastname: Muñoz
mesh_terms: D018906:Antineoplastic Agents, Alkylating / Q000737:chemistry; D001388:Aziridines; D002699:Chlorambucil / Q000737:chemistry*; D006868:Hydrolysis; D007700:Kinetics; D008956:Models, Chemical; D013816:Thermodynamics
chemical_list: D018906:Antineoplastic Agents, Alkylating; D001388:Aziridines; D002699:Chlorambucil; C033132:aziridine