- One-pot synthesis, structure, theoretical study and vibrational spectroscopy of 5-amino-4-cyano-3H-1,2-dithiole-3-thione
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A novel D3T derivative, 5-amino-4-cyano-3H-1,2-dithiole-3-thione (compound 1) has been obtained in one-pot reaction. The crystal is orthorhombic, space group Pbca, with a = 10.3667(4) ?, b = 10.8898(4) ?, c = 11.4942(5) ?, V = 1297.60(9) ?3, and Z = 8. In the crystal, molecules are firstly self-assembled into a complex sheet parallel to the (0 0 1) plane containing centrosymmetric R24 (16) and R44 (24) rings, and then the interconnection of molecular sheets through S···S interactions forms a three-dimensional supramolecular assembly. The DFT calculations are performed for isolated molecule using the B3LYP/6-31+G(d,p) methods. The frontier orbital properties of compound 1 have been reported and discussed. Moreover, a detailed assignment of the fundamental vibrational modes is proposed on the basis of the calculated results.
- Cao, Yanning,Zhang, Hanhui,Lin, Yiji,Huang, Changcang,Chen, Yiping,Zhang, Fengli,Chen, Jianshan
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- Cyclizations of Cyanothioacetamide in the Presence of Sulphur
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Cyanothioacetoamide 1 reacts with sulphur in the presence of triethylamine to form the 2,5-diamino-thiophene derivative 3 and in the presence of sodium ethoxide the 1,4-dihydropyridine derivative 2, respectively. 3 easily undergoes ring opening to yield the butadiene derivative 6.Catalyzed by amine from 1, cyclic ketones, and sulphur the 2-spiropyrimidine-4-thiones> 8 arise.Analogously to other cyanoacetic acid derivatives 1 react with sulphur and isothiocyanates to form the 4-amino-Δ4-thiazoline-2-thiones 9 and with sulphur and carbon disulfide to yield the 5-amino-1,2-dithiol-3-thione derivative 12.Among the o-amino-thiocarboxamides 3, 9, 12 the compounds 3 and 9 can be converted into the 5,6-heterocondensed pyrimidine-4-thiones 4 and 10.
- Gewald, K.,Schindler, R.
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p. 223 - 228
(2007/10/02)
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