Radical anions of 3,3'-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1'-dioxides in MeCN-H2O solvent mixtures

Radical anions of 3,3'-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1'-dioxides in MeCN-H2O solvent mixtures Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2009, Volume: 58, Number: 8, Pages: 1681-1687 Pages count : DOI: 10.1007/s11172-009-0232-y

Tags

3,3 '-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1 '-dioxides; cyclic nitrones; dinitrones; radical anions; electrochemical reduction; ESR spectroscopy; DFT; UB3LYP; PCM quantum chemical calculations

Authors

Shundrin L. A. ¹ , Irtegova I. G. ¹ , Vasil'eva N. V. ¹ , Reznikov V. A. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

Radical anions of cyclic dinitrones, 3,3'-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1'-dioxides (R = Me, Ph, Bu-t, CF3) have been studied by ESR in combination with quantum chemical calculations of geometrical parameters and isotropic hyperfine interaction constants by the DFT/PBE methods in the 3z basis set and UB3LYP in the 6-31+G* basis set with allowance for the solvation in the framework of continual PCM model. The radical anions were generated electrochemically by reduction of their neutral precursors in MeCN-H2O solvent mixtures and found to possess enough stability for measurement of their ESR spectra in a wide range of the mixture compositions. Radical anions of compounds of nitrone series were generated and characterized in MeCN-H2O mixtures and water (for the dinitrone with R = Me) for the first time. Differences in the solvent depending behavior of the nitrogen hyperfine interaction constants in the series of radical anions with various substituents R are explained by competition of transsolvation and structural effects.

Shundrin L.A. , Irtegova I.G. , Vasil'eva N.V. , Reznikov V.A.
Radical anions of 3,3'-bi(2-R-5,5-dimethyl-4-oxopyrrolinylidene) 1,1'-dioxides in MeCN-H2O solvent mixtures
Russian Chemical Bulletin. 2009. V.58. N8. P.1681-1687. DOI: 10.1007/s11172-009-0232-y WOS Scopus РИНЦ OpenAlex

Published print:	Aug 1, 2009
Published online:	Jun 6, 2010

Web of science:	WOS:000278470900020
Scopus:	2-s2.0-77955745262
Elibrary:	15308570
OpenAlex:	W2065130441

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