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Journal of Structural Chemistry

2011 year, number 1

Gas electron diffraction and quantum chemical Studies of THE Molecular structure of 2-nitrobenzenesulfonic acid

V. M. Petrov1, N. I. Giricheva2, G. V. Girichev3, V. N. Petrova4, S. N. Ivanov5, A. V. Bardina6
Keywords: 2-nitrobenzenesulfonic acid, conformer, molecular structure, gas electron diffraction, quantum chemistry, mass-spectrometry
Pages: 65-73


A combined gas electron diffraction and quantum chemical (B3LYP/6-311+G**, B3LYP/cc-pVTZ) study of the molecular structure of 2-nitrobenzenesulfonic acid (2-NBSA) is performed. Quantum chemical calculations show that the 2-NBSA molecule has five conformers, and the Gibbs energy of one of them is lower by more than 4.5 kcal/mol than the energy of the other conformers. It is found experimentally that the saturated vapor of 2-NBSA at Т = 394(5) K contains only the low-energy conformer that has an intramolecular hydrogen bond between the H atom of the hydroxyl group and one of the О atoms of the NO2 group. The C-C-S-O(Н) torsion angle determining the position of the S-O(Н) bond is -72(7)°, while the NO2 group is substantially turned relative to the benzene ring plane (C1-C2-N-O = 40(5)°). The following experimental values of the internuclear distances are obtained for this conformer (Å): rh1(C-H)av = 1.07(2), rh1(C-C)av = 1.401(4), rh1(C-S) = 1.767(6), rh1(S=O)av = 1.412(4), rh1(S-O) = 1.560(6), rh1(N-O)av = 1.217(5), rh1(C-N) = 1.461(8), rh1(O-H) = 0.99(3).