It is thought that most arylamines can be oxidized to hydroxylamine and are further activated to carboxyl and sulfate esters. However, only some arylamines are mutagenic, reacting with purine bases resulting in modified DNA, primarily at the C8 position of guanine. To study the mechanisms of the reaction of the activated arylamines and guanine, we examined the initial substitution reaction. The energy barriers to the transition states were calculated, in which guanine at the N7 position reacts with the activated arylamine, in an S<sub>N</sub>2 or S<sub>N</sub>2’ fashion. We modeled these reactions using both gas and aqueous SMD solvation models, with the basis sets of 6-31+G and 6-31+G(d). We utilized calculation methods, BPBE, B98, BP86, B3LYP, and PBE1PBE, to study these reactions and the results will be presented.

Comparison of density functional methods for initial SN2 and SN2’ reactions of guanine with activated arylamines

251st National Meeting (2016)

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