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Quantum-chemical study of nitrosonium complexes derived from nitrogen-containing heterocycles

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Abstract

The affinities of a series of azines for nitrosonium ion (A NO +) were calculated by quantum-chemical methods, AM1 and ab initio. The A NO + values were found to increase as the number of nitrogen atoms in the ring decreases and the donor power of substituents increases; ring fusion also increases A NO +. The best agreement between the calculated and experimental A NO + values was attained with the use of AM1 calculations and ab initio methods with split polarization or diffuse functions. Substituted pyridines showed linear correlations between the calculated A NO + values and substituent constants σ or σ+ or overall charges on the NO group in the complex. Linear correlations were also found between the calculated A NO + values of azines and their experimental proton affinities.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    R. V. Andreev, G. I. Borodkin & V. G. Shubin

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  1. R. V. Andreev
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  2. G. I. Borodkin
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  3. V. G. Shubin
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Additional information

Original Russian Text © R.V. Andreev, G.I. Borodkin, V.G. Shubin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 10, pp. 1562–1573.

For preliminary communications, see [1, 2].

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Andreev, R.V., Borodkin, G.I. & Shubin, V.G. Quantum-chemical study of nitrosonium complexes derived from nitrogen-containing heterocycles. Russ J Org Chem 42, 1551–1562 (2006). https://doi.org/10.1134/S1070428006100265

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