Abstract
A combined gas electron diffraction and quantum chemical (B3LYP/6-311+G**, B3LYP/cc-pVTZ, B3LYP/cc-pVTZ, midix (Cl), and MP2/cc-pVTZ) study of the structure of a 2-NO2-C6H4-SO2Cl molecule is performed. It is found experimentally that at a temperature of 345(5) K the gas phase contains two conformers of the C 1 symmetry. Conformer I with a nearly perpendicular arrangement of the S-Cl bond with respect to the benzene ring plane (the C(NO2)-C-S-Cl torsion angle is 84(3)°) is contained predominantly (69(12)%). In conformer II, the S-Cl bond is located near the benzene ring plane (the C(NO2)-C-S-Cl angle is 172(3)°). The following experimental internuclear distances (Å) are obtained for conformer I: r h1(C-H) = 1.064(15), r h1(C-C)av = 1.397(3), r h1(C-S) = 1.761(6), r h1(S-O)av = 1.426(4), r h1(S-Cl) = 2.043(5), r h1(N-O)av = 1.222(4), r h1(C-N) = 1.485(16). In both conformers, the NO2 group is turned by more than 30° relative to the benzene ring plane.
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Original Russian Text Copyright © 2011 by V. M. Petrov, N. I. Giricheva, G. V. Girichev, A. V. Bardina, V. N. Petrova, and S. N. Ivanov
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Translated from Zhurnal Strukturnoi Khimii, Vol. 52, No. 4, pp. 711–720, July–August, 2011.
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Petrov, V.M., Giricheva, N.I., Girichev, G.V. et al. Gas electron diffraction and quantum chemical study of the structure of a 2-nitrobenzenesulfonyl chloride molecule. J Struct Chem 52, 690–698 (2011). https://doi.org/10.1134/S002247661104007X
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DOI: https://doi.org/10.1134/S002247661104007X