3297-15-2Relevant academic research and scientific papers
Effect of substitution of oxygen by sulfur in the npnleaving group of a carbonate: Kinetics of the phenolysis and benzenethiolysis of 5-methyl aryl thiocarbonates
Castro, Enrique A.,Aliaga, Margarita,Santos, Jose G.
, p. 533 - 538 (2007)
The phenolysis and benzenethiolysis of S-methyl 4-nitrophenyl thiocarbonate (1) and S-methyl 2,4-dinitrophenyl thiocarbonate (2) in water are studied kinetically. The Brnsted plots (log kN versus nucleophile basicity) are linear for all reactions. The Bronsted slopes for 1 and 2 are, 0.51 and 0.66 (phenolysis) and 0.55 and 0.70 (benzenethiolysis), respectively. These values suggest a concerted mechanism for these reactions, as found in the corresponding carbonates. Namely, substitution of OMe by SMe in the nonleaving group does not change the mechanism. Copyright 2007 John Wiley & Sons, Ltd.
