Structures and properties of 1,4-dithiins and related molecules


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Abstract

A series of organosulfur compounds was characterized by NMR, IR, mass spectroscopy, cyclic voltammetry, and chemical analyses. The crystal structures of six compounds were determined: 1,3-dithioleno[4,5-e]naphtho[2,3-b]1,4-dithiin-2,5, 10-trione (1b), P1, a = 7.665(4), b = 7.997(4), c = 11.443(5) Å, α = 91.311(8), β = 92.516(8), γ = 117.53(7)°; 6,7-dimethylbenzo[1,2-b]1,3-dithioleno[4,5-e]1,4-dithiin-2,5,8-trione (2b), P21/m, a = 3.933(1), b = 12.864(2), c = 11.943(3) Å, β = 99.161(4)°; 6-phenyl-2-thioxo-6-hydrocyclopenta[2,1-b]1,3-dithioleno[4,5-e]1,4-dithiin-5,7-dione (3a), C2/c, a = 32.408(6), b = 3.8743(8), c = 27.123(5) Å, β = 125.171(7)°; 6-phenyl-1,3-dithioleno[4,5-e]3-pyrrolino[3,4-b]1,4-dithiin-5,7-trione (3b), P21/n, a = 7.9712(9), b = 6.1976(7), c = 55.978(6) Å, β = 91.096(1)°; 2,3,7,8-tetramethylthianthrene-1,4,6,9-tetraone (4), P21/c, a = 4.195(1), b = 17.924(5), c = 9.682(3) Å, β = 98.509(5)°; 3H,6H-1,4-oxathiino[6′,5′-2,1]naphtho[3,4-e]1,4-oxathiin-2,7-dione (5), P21/n, a = 9.3522(7), b = 7.8782(6), c = 17.118(1) Å, β = 93.171(1)°. Several structures exhibited significant S—S intermolecular interactions, suggesting that the molecules might be precursors for preparing nonmetallic conductors.

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