Second-order rate constants have been determined for the title reactions in OH-/H2O and in OH-/(CH3CN/H2O) [30/70, 60/40, and 85/15 (v/v) mixtures]. A relatively small increase in reactivity is observed for the four substrates upon increasing the percentage of CH3CN in the solvent mixture. The methyl activating factors (kOHN(CH3)/kOH(N)) are also slightly affected by the solvent composition. On the other hand, the high acceleration of the reaction by methylation of the pyridine ring amounts to 104-106 according to an E1cb mechanism.
A Study of the OH--induced beta-Elimination Reactions of 2-(4-Chloroethyl)pyridine, 2-(2-Chloroethyl)pyridine, 1-Methyl-2-(4-Chloroethyl)pyridinium iodide and 1-Methyl-2-(2-Chloroethyl)pyridinium iodide in Acetonitrile/Water
DE MARIA, Paolo;FONTANA, Antonella;GASBARRI, Carla;
2004-01-01
Abstract
Second-order rate constants have been determined for the title reactions in OH-/H2O and in OH-/(CH3CN/H2O) [30/70, 60/40, and 85/15 (v/v) mixtures]. A relatively small increase in reactivity is observed for the four substrates upon increasing the percentage of CH3CN in the solvent mixture. The methyl activating factors (kOHN(CH3)/kOH(N)) are also slightly affected by the solvent composition. On the other hand, the high acceleration of the reaction by methylation of the pyridine ring amounts to 104-106 according to an E1cb mechanism.File in questo prodotto:
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