Artículos de revistas
Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
Fecha
2017-02Registro en:
Saeed, Aamer; Ashraf, Zaman; Erben, Mauricio Federico; Simpson, Jim; Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas; Elsevier Science; Journal of Molecular Structure; 1129; 2-2017; 283-291
0022-2860
CONICET Digital
CONICET
Autor
Saeed, Aamer
Ashraf, Zaman
Erben, Mauricio Federico
Simpson, Jim
Resumen
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 NH⋯O and intermolecular NH⋯S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(CO) and ν(CS) 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 NH⋯OC 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.