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Intermolecular forces and functional group effects in the packing structure of thiophene derivatives
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Thiophene was derivatized at the ?-carbon with isophthalic, dipicolinic, and four nitrobenzoic acids to yield 4-thiophen-3-yl-pyridine-2,6-dicarboxylic acid diethyl ester, I; 5-thiophen-3-yl-isophthalic acid diethyl ester, II; 2-nitro-4-thiophen-3-yl benzoic acid ethyl ester, III; 3-nitro-4-thiophen-3-yl benzoic acid ethyl ester, IV; 3-nitro-2-thiophen-3-yl benzoic acid ethyl ester, V; and 2-nitro-5-thiophen-3-yl benzoic acid ethyl ester, VI. These resulting compounds have been isolated and characterized by X-ray single-crystal diffraction. The solid-state structures of these substances are discussed as a function of the position and nature of the functional groups and the intermolecular forces. Modeling of the thiophene?aromatic ring torsion angle allowed us to attribute large differences in torsion angles to packing effects in the structures, due to ??? interactions between the aromatic rings.