Reductive activation of arenes 20. Anionic products of two-electron reduction of tolunitriles in liquid ammonia: the nature and electronic structure

Reductive activation of arenes 20. Anionic products of two-electron reduction of tolunitriles in liquid ammonia: the nature and electronic structure Full article

Journal

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

Output data

Year: 2006, Volume: 55, Number: 6, Pages: 976-980 Pages count : DOI: 10.1007/s11172-006-0365-1

Tags

aromatic nitriles; reduction in liquid ammonia; cyanocyclohexadienyl anions; NMR spectroscopy; quantum chemical calculations; linear correlations

Authors

Vaganova T. A. , Yuferov P. S. , Goryunov L. L. , Panteleeva E. V. , Sal'nikov G. E. , Shchegoleva L. N. , Mamatyuk V. L. , Shteingarts V. D.

Affiliations

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

Stable cyanomethylcyclohexadienyl anions generated in two-electron reduction of isomeric tolunitriles by potassium in liquid ammonia were detected by NMR spectroscopy. The chemical shifts in these anions were obtained from density functional (PBE/3z) quantum chemical calculations and the electron density distributions for the anions were calculated in the framework of the NBO approachat the HF/6-31+G* level of theory. The experimental and calculated delta(C) values are in good agreement. Changes in the delta(C) values on going from the starting nitriles to the corresponding anions are linearly related to the calculated pi-electron densities on the pentadienyl ring carbon atoms.

Vaganova T.A. , Yuferov P.S. , Goryunov L.L. , Panteleeva E.V. , Sal'nikov G.E. , Shchegoleva L.N. , Mamatyuk V.L. , Shteingarts V.D.
Reductive activation of arenes 20. Anionic products of two-electron reduction of tolunitriles in liquid ammonia: the nature and electronic structure
Russian Chemical Bulletin. 2006. V.55. N6. P.976-980. DOI: 10.1007/s11172-006-0365-1 WOS Scopus РИНЦ

Published print:

Jun 1, 2006

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