Nucleophilic reactivity of thiolate, hydroxide, and phenolate ions toward a model O2??arylated diazeniumdiolate prodrug in aqueous and cationic surfactant media

…, SE Price, J Ta, KM Davies

Index: Ning, Matthew S.; Price, Stacy E.; Ta, Jackie; Davies, Keith M. Journal of Physical Organic Chemistry, 2010 , vol. 23, # 3 p. 220 - 226

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Citation Number: 7

Abstract

Abstract The kinetics of aromatic nucleophilic substitution of the nitric oxide-generating diazeniumdiolate ion, DEA/NO, by thiols (L-glutathione, L-cysteine, DL-homocysteine, 1- propanethiol, 2-mercaptoethanol, and sodium thioglycolate) from the prodrug, DNP- DEA/NO, has been examined in aqueous solution and in solutions of cationic DOTAP vesicles. Second-order rate constants in buffered aqueous solutions (k RS-= 3.48–30.9 M ...