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Molecules 2010, 15(1), 554-569; doi:10.3390/molecules15010554
Article

Structure, Morphology and Optical Properties of Chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2

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Received: 22 December 2009 / Revised: 14 January 2010 / Accepted: 21 January 2010 / Published: 26 January 2010
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Abstract

Three new enantiopure aryl-thioureas have been synthesized, N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2 (compounds 1-3, respectively). Large single crystals of up to 0.5 cm3 were grown from methanol/ethanol solutions. Molecular structures were derived from X-ray diffraction studies and the crystal morphology was compared to calculations employing the Bravais-Friedel, Donnay-Harker model. Molecular packing was further studied with Hirshfeld surface calculations. Semi-empirical classical model calculations of refractive indices, optical rotation and the electro-optic effect were performed with OPTACT on the basis of experimentally determined refractive indices. Compound 3 (space group P 1 (No. 1)) was estimated to possess a large electro-optic coefficient r333 of approximately 30 pm/V, whereas 1 and 2 (space Group P 21 (No. 4) exhibit much smaller effects.
Keywords: aryl ureas; enantiopure crystals; X-ray diffraction; thioamide dimer; non-linear optical properties; Hirshfeld surfaces; OPTACT; dipole-dipole interaction; Bravais-Friedel; Donnay-Harker aryl ureas; enantiopure crystals; X-ray diffraction; thioamide dimer; non-linear optical properties; Hirshfeld surfaces; OPTACT; dipole-dipole interaction; Bravais-Friedel; Donnay-Harker
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kaminsky, W.; Responte, D.; Daranciang, D.; Gallegos, J.B.; Ngoc Tran, B.-C.; Pham, T.-A. Structure, Morphology and Optical Properties of Chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2. Molecules 2010, 15, 554-569.

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