کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1409347 | 1501751 | 2014 | 10 صفحه PDF | دانلود رایگان |
• Three 1-(adamantane-1-carbonyl)-3-substituted thioureas were prepared for the first time.
• Crystal and molecular structures were determined.
• Both intra- and inter-molecular hydrogen bonds are found in the crystal.
• Conformational aspects are discussed in terms of the vibrational spectra.
• The role of the substituent attached to the thiourea group is discussed.
Three novel 1-(adamantane-1-carbonyl) thioureas were synthesized by the reaction of adamantyl isothiocyante with corresponding amines and fully characterized by spectroscopy methods. Two isomeric species, i.e. 1-(adamantane-1-carbonyl)-3-(3-nitrophenyl)thiourea (1) and 1-(adamantane-1-carbonyl)-3-(4-nitrophenyl)thiourea (2), are structurally characterized and a third related compound, namely 1-(adamantane-1-carbonyl)-3,3-(methyl-phenyl)thiourea (3) has been also included for assessing the role of the nitrogen substitution on the structural properties. As determined by X-ray analysis, compounds 1 and 2 exhibit the S conformation with the CO and CS double bonds in a pseudo-antiperiplanar orientation, whereas the U form is found for compound 3. These conformational features are mainly dictated by the substitution degree on the thiourea core and the ability of forming an intra-molecular NH⋯OC hydrogen bond for mono-substituted analogues 1 and 2. These dissimilar interactions affect the vibrational properties, which have been determined by infrared and Raman spectroscopies and quantum chemical calculations at the B3LYP/6-311++G** level of approximation.
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Journal: Journal of Molecular Structure - Volumes 1065–1066, 22 May 2014, Pages 150–159