Journal of Siberian Federal University. Chemistry / Relationship Between Geometrical Structure and Acid Properties of Exhaustively Substituted Nitrosophenols with Pyridine Substituents

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Issue
Journal of Siberian Federal University. Chemistry. 2017 10 (4)
Authors
Kukushkin, Aleksey A.; Krasnov, Pavel O.; Root, Evgeniy V.; Suboch, Georgy A.; Tovbis, Mikhail S.
Contact information
Kukushkin, Aleksey A.: Reshetnev Siberian State University of Science and Technology 31 Krasnoyarskiy rabochiy, Krasnoyarsk, 660037, Russia; Krasnov, Pavel O.: Reshetnev Siberian State University of Science and Technology 31 Krasnoyarskiy rabochiy, Krasnoyarsk, 660037, Russia; Siberian Federal University 79 Svobodny, Krasnoyarsk, 660041, Russia; Root, Evgeniy V.: Reshetnev Siberian State University of Science and Technology 31 Krasnoyarskiy rabochiy, Krasnoyarsk, 660037, Russia; Krasnoyarsk State Medical University named after Prof. V.F. Voino-Yasenetsky 1 Partizana Zheleznyaka, Krasnoyarsk, 660022, Russia; Suboch, Georgy A.: Reshetnev Siberian State University of Science and Technology 31 Krasnoyarskiy rabochiy, Krasnoyarsk, 660037, Russia; Tovbis, Mikhail S.: Reshetnev Siberian State University of Science and Technology 31 Krasnoyarskiy rabochiy, Krasnoyarsk, 660037, Russia;
Keywords
exhaustively substituted nitrosophenols; acidity constant; pyridine substituents; quantum chemical calculations; coplanarity; orthogonality
Abstract

The acidity constants of the exhaustively substituted nitrosophenols with phenyl and ester substituents are determined. It was found that these compounds are more acidic than nitrosophenols with methyl groups, but less acidity than the persubstituted nitrosophenols with pyridine substituents. Quantumchemical calculations, performed by the method of stationary density functional theory using exchangecorrelation functional BP86 and def2-SVP basis set, have shown that the pyridine and nitrosophenol rings occupy an intermediate position between the orthogonal and coplanar functional. Thus, the hypothesis of a possible electron-withdrawing effect of the nitrogen atom of pyridine rings not only through the system of σ-bonds, but also due to the mesomeric effect through the residual coupling of π-systems is confirmed

Pages
580-586
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/70364