Reductive activation of arenes |
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| Authors: | T. A. Vaganova P. S. Yuferov L. I. Goryunov E. V. Panteleeva G. E. Sal’nikov L. N. Shchegoleva V. I. Mamatyuk V. D. Shteingarts |
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| Affiliation: | (1) N. N. Vorozhtsov Novosibirsk Iinstitute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090 Novosibirsk, Russian Federation;(2) Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation |
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| Abstract: | 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 approach at the HF/6-31+G* level of theory. The experimental and calculated δC values are in good agreement. Changes in the δC values on going from the starting nitriles to the corresponding anions are linearly related to the calculated π-electron densities on the pentadienyl ring carbon atoms. Dedicated to the memory of Academician V. A. Koptyug on the occasion of the 75th anniversary of his birth. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 940–944, June, 2006. |
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| Keywords: | aromatic nitriles reduction in liquid ammonia cyanocyclohexadienyl anions NMR spectroscopy quantum chemical calculations linear correlations |
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