Abstract: Relative rates of the amination of 3-X- and 4-X-substituted pyridines (X = H, 3-Me, 4-Me, 3-F3C, 3-CN, 4-CN, 3-Cl, 3-Br, 4-MeO, 4-Me2N), pyrazine, quinoline, isoquinoline, 2,2'- and 4,4'-bipyridines, and 1,10-phenanthroline with O-mesitylenesulfonylhydroxylamine were estimated by NMR spectroscopy. Correlations were found between logarithms of the relative amination rate constants and substituent constants sigma or sigma(I) and sigma(R) for X-substituted pyridines. A wide series of nitrogen-containing heterocyclic compounds turned out to fit correlations between logarithms of the relative amination rate constants, on the one hand, and relative stabilities of N-aminoazinium cations, energies of activation of the amination process, and gas-phase proton affinities, calculated by the DFT/PBE/3z and DFT/B3LYP/L2 methods, on the other.

Cite: Borodkin G.I. , Vorob'ev A.Y. , Shubin V.G.
Structure-kinetics relations holding in the amination of six-membered nitrogen-containing heterocyclic compounds
Russian Journal of Organic Chemistry. 2011. V.47. N6. P.897-903. DOI: 10.1134/S107042801106011X WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Бородкин Г.И. , Воробьев А.Ю. , Шубин В.Г.
Структурно-кинетические закономерности аминирования шестичленных n-гетероароматических соединений
Журнал органической химии (RUSS J ORG CHEM+). 2011. Т.47. №6. С.21-22. РИНЦ

Dates:

Published print:	Jun 1, 2011
Published online:	Jul 8, 2011

Identifiers:

Web of science	WOS:000292562900011
Scopus	2-s2.0-80051524373
Elibrary	18058369
OpenAlex	W2026473417

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