ACTION D'ISOTHIOCYANATES SUR LES CARBANIONS DÉRIVÉS D'α-ALCOYL PYRIDINES ET D'α-ALCOYL QUINOLEINES STRUCTURE CRISTALLINE DE L'α,α',-di (N-PARATOLYLTHIOCARBOXAMIDE) PICOLINE-2

Pascual, S.;Escudier, MC.;Lamazouere, AM.;Sotiropoulos, J.;Germain, Gabriel;et.al.
(1993) Phosphorous and Sulfur and the Related Elements — Vol. 78, n° 1-4, p. 97-108 (1993)

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  • Pascual, S.
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  • Escudier, MC.
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  • Lamazouere, AM.
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  • Sotiropoulos, J.
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  • Germain, GabrielUCLouvain
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Abstract
Carbanions derived from 2-alkyl pyridines and 2-alkyl quinolines react with one or two molecules of isothiocyanate, depending upon the carbanion and isothiocyanate structures. Thiocarboxamides 12, 13, or dithiocarboxamides 1, 3, 5, 7, 9, 11, are obtained. When dithiocarboxamides are formed, cyclisation occurs by further oxidation giving a dithiolan derivative. A single crystal structure study of one of these dithiocarboxamides was carried out. The crystals belong to space group P2(1)/c, with a = 12.874 (1), b = 10.867 (1), c = 15.624 (1) angstrom, beta = 109.13 (1)-degrees, Z = 4, M = 389.54, D(x) = 1.253 g cm-3, mu = 2.3 mm-1, F (000) = 816. The packing of molecules show stocking with two hydrogen bonds: N-H . . . N (N-N distance 2.673 angstrom) and N-H . . . S (N-S distance 3.338 angstrom).
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Pascual, S., Escudier, MC., Lamazouere, AM., Sotiropoulos, J., Dupont, L., Dideberg, O., & Germain, G. (1993). ACTION D’ISOTHIOCYANATES SUR LES CARBANIONS DÉRIVÉS D’α-ALCOYL PYRIDINES ET D’α-ALCOYL QUINOLEINES STRUCTURE CRISTALLINE DE L’α,α’,-di (N-PARATOLYLTHIOCARBOXAMIDE) PICOLINE-2. Phosphorous and Sulfur and the Related Elements, 78(1-4), 97-108. https://doi.org/10.1080/10426509308032426 (Original work published 1993)