A. Saeed, Z. Ashraf, M. Erben
Feb 5, 2017
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0
Influential Citations
24
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract 1-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1 , and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2 , were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular N H⋯O and intermolecular N H⋯S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(C O) and ν(C S) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular N H⋯O C hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl⋯Cl halogen bond.