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

Molecules

Werner Kaminsky¹  Donald Responte¹  Dan Daranciang¹  Jose B. Gallegos¹  Bao-Chau Ngoc Tran¹ 

[1] Department of Chemistry, University of Washington, Seattle, Washington 98195, USA

关键词: aryl ureas;    enantiopure crystals;    X-ray diffraction;    thioamide dimer;    non-linear optical properties;    Hirshfeld surfaces;    OPTACT;    dipole-dipole interaction;    Bravais-Friedel;    Donnay-Harker;   

DOI  :  10.3390/molecules15010554

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.