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

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

Department of Chemistry, University of Washington, Seattle, Washington 98195, USA
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Author to whom correspondence should be addressed.
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
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

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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