Reaction Kinetics of the Benzylation of Adenine in DMSO: Regio-Selectivity Guided by Entropy.

ABSTRACT: The factors governing the regio-selectivity of the alkylation of adenine have been of interest for many years due to the biological importance of adenine derivatives, however, no reaction kinetic studies have been conducted. Herein, we report the rate constants and activation parameters of the benzylation of adenine under basic conditions in DMSO in the absence and presence of 15-crown-5 ether using real-time ¹H NMR spectroscopy. The reaction is second-order for the formation of the N9- and N3-benzyladenine products, with a regio-selectivity factor 2.3 in favour of the N9-adduct. The Gibbs free energy of activation amounts to 87±2 kJ mol^-1 for both reactions. The formation of the N9-adduct is more activated by 7 kJ mol^-1, but its effect is offset by a less

SUBMITTER: Buyens DMS 

PROVIDER: S-EPMC11614369 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature