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Quantum-chemical study of nitrosonium complexes of monocyclic aromatic compounds

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Abstract

With the use of Hartree-Fock and DFT methods we demonstrated that for the benzene derivatives with the substituents Me, Et, Pr, i-Pr, t-Bu, CF3, F, and Cl π-complexes are more favorable by energy, whereas with the substituents CHO, MeCO, PhCO, CN, NO, and NO2 n-complexes are more feasible. The affi nity of aromatic compounds to the nitrosonium-cation (ANO+) at the formation of the π-complexes grows with the growing donor character of the substituents in the ring and with their number. The best agreement between the calculated and experimental ANO+ values for benzene was obtained with the use of RI-MP2/L1 method.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, 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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Correspondence to R. V. Andreev.

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Original Russian Text © R.V. Andreev, G.I. Borodkin, V.G. Shubin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 11, pp. 1669–1674

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Andreev, R.V., Borodkin, G.I. & Shubin, V.G. Quantum-chemical study of nitrosonium complexes of monocyclic aromatic compounds. Russ J Org Chem 47, 1703–1709 (2011). https://doi.org/10.1134/S107042801111008X

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  • DOI: https://doi.org/10.1134/S107042801111008X

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