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Structure, morphology and optical properties of chiral N-(4-X-phenyl)-N-[1(S)-1-phenylethyl]thiourea, X= Cl, Br, and NO2

Molecules. 2010 Jan 26;15(1):554-69. doi: 10.3390/molecules15010554.

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 cm(3) 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 r(333) of approximately 30 pm/V, whereas 1 and 2 (space Group P 2(1) (No. 4) exhibit much smaller effects.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Bromine / chemistry*
  • Chlorine / chemistry*
  • Crystallography, X-Ray
  • Electrons
  • Hydrogen Bonding
  • Models, Molecular
  • Nitrogen Dioxide / chemistry*
  • Optical Phenomena*
  • Refractometry
  • Rotation
  • Thioamides / chemistry
  • Thiourea / chemical synthesis
  • Thiourea / chemistry*

Substances

  • Thioamides
  • Chlorine
  • Thiourea
  • Nitrogen Dioxide
  • Bromine