Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan.
Spectrochim Acta A Mol Biomol Spectrosc. 2013 Feb;102:408-13. doi: 10.1016/j.saa.2012.10.043. Epub 2012 Nov 1.
1-(Adamantane-1-carbonyl)-3-(2,4-dichlorophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)-3-(2-bromo-4,6-difluorophenyl)thiourea (2) were synthesized by the reaction of adamantane-1-carbonyl chloride with ammonium thiocyanate to afford the adamantane-1-carbonylisothiocyanate in situ followed by treatment with suitable halogenated anilines. The structures of the products were established by elemental analyses, Fourier transform infrared spectroscopy (FTIR), (1)H, (13)C nuclear magnetic resonance (NMR), mass spectroscopy and single crystal X-ray diffraction study. Bond lengths and angles show the usual values. All of three condensed cyclohexane rings of the adamantane residues adopt the usual chair conformation. The molecular conformation of 1 and 2 is stabilized by an intramolecular (NH⋯OC) hydrogen bond which forms a pseudo-six-membered ring. Structural features have been complemented with the joint analysis of the FTIR and FT-Raman spectra along with quantum chemical calculations at the B3LYP/6-311++G level.
1-(金刚烷-1-羰基)-3-(2,4-二氯苯基)硫脲（1）和 1-(金刚烷-1-羰基)-3-(2-溴-4,6-二氟苯基)硫脲（2）是通过金刚烷-1-碳酰氯与硫氰酸铵反应原位生成金刚烷-1-碳异硫氰酸酯，然后用合适的卤代苯胺处理合成的。产物的结构通过元素分析、傅里叶变换红外光谱（FTIR）、（1）H、（13）C 核磁共振（NMR）、质谱和单晶 X 射线衍射研究确定。键长和键角呈现出通常的数值。金刚烷残基的所有三个稠合环己烷环均采用通常的椅式构象。1 和 2 的分子构象通过分子内（NH⋯OC）氢键稳定，形成一个拟六元环。结构特征通过 FTIR 和 FT-Raman 光谱的联合分析以及在 B3LYP/6-311++G 水平的量子化学计算得到了补充。
