Arylsulfonylation of N-isobutylaniline and its derivatives: experimental study and quantum-chemical calculationsстатья
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Дата последнего поиска статьи во внешних источниках: 23 сентября 2021 г.
Аннотация:The kinetics of the reactions of benzenesubstituted Nisobutylanilines 1a—h with
3nitrobenzenesulfonyl chloride in propan2ol was studied at 298 K. To analyze the reactivi
ties of compounds 1a—h in the arylsulfonylation reactions and substantiate the possible mecha
nism of these reactions, the geometric, electronic, and energy characteristics of the reagents
and a series of model compounds were calculated by the semiempirical quantumchemical
AM1 and PM3 methods. The rate of arylsulfonylation of Nisobutylaniline and its derivatives
increases directly proportional to the contributions of the s and pz orbitals of the N atoms to
HOMO of amine and of the S atoms to LUMO of sulfonyl chloride. The coefficients of these
AOs can be considered as the reactivity indices of the reagents used for arylsulfonylation of
substituted Nisobutylanilines with aromatic sulfonyl chlorides. It was proposed that the reac
tion under study is orbitalcontrolled.