Abstract
A combined gas-phase electron diffraction and quantum chemical (B3LYP/cc-pVTZ, MP2/cc-pVDZ) study of molecular structure of 2,4,6-trinitrobenzenesulfonic acid (2,4,6-tri-NBSA) was carried out. Quantum chemical calculations showed that 2,4,6-tri-NBSA possesses six conformers, which form three pairs of enantiomers with the relative energy of 0, 4.4/3.9, and 2.5/2.5 kcal/mol. It was experimentally established that at T = 444(5) K a saturated vapor over 2,4,6-tri-NBSA is, predominantly (up to 93 mol.%), represented by a low-energy enantiomers II and II′ characterized by intramolecular hydrogen bond between an H atom of the hydroxyl group and one of the O atoms of the NO2 group. Experimental internuclear distances for the low-energy enantiomers are (A): r h1(C–C)av. = 1.387(4), r h1(C–S) = 1.811(6), r h1(S=O)av. = 1.424(4), r h1(S–O) = 1.579(4), r h1(N–O)av. = 1.214(3), r h1(C–N)av. = 1.491(5). Geometry of the conformer II points on existance of strong steric interactions between SO2OH group and two ortho-nitro groups. Analysis of the orbital interactions between the substituents and benzene ring was carried out. Geometric parameters and energies of transition states between conformers were calculated (B3LYP).
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