133041-51-7Relevant articles and documents
Hydrolysis and Alkylating Reactivity of Aromatic Nitrogen Mustards
O'Connor, Charmian J.,Denny, William A.,Fan, Jun-Yao,Gravatt, G. Lance,Grigor, Bruce A.,McLennan, Duncan J.
, p. 1933 - 1940 (2007/10/02)
Rate constants for the hydrolysis of a series of aromatic nitrogen mustards Ar-X-C6H4-N(CH2CH2Cl)2 (X = O, CH2, CONH, S, CO and SO2) in buffered aqueous acetone mixtures have been obtained using HPLC technique which allows evaluation of the rate constants for hydrolytic displacement of both chlorines in consecutive reactions.Hydrolysis has a general-base-catalysed component and is accompanied by external chloride ion return.An aziridinium ion intermediate is implicated in at least one pathway.The mustards also alkylate the nucleophiles thiourea and4-(4-nitrobenzyl)-pyridine (NBP) and again the aziridinium ion intermediate is involved since the kinetic behaviour rules out a direct SN2 pathway.