N-4-（bromobutanoyl）-N＇-（o-, m- and p-tolyl）thioureas 3a, 3b and 3c respectively, were synthesized by the reaction of 4-bromobutanoylisothiocyanate with p-, m- and o-toludine. The products were characterized by IR...N-4-（bromobutanoyl）-N＇-（o-, m- and p-tolyl）thioureas 3a, 3b and 3c respectively, were synthesized by the reaction of 4-bromobutanoylisothiocyanate with p-, m- and o-toludine. The products were characterized by IR, and NMR spectroscopic techniques. The two carbonoylthiourea isomers N-（4-bromobutanoyl）-N＇-（3-methylphenyl）thiourea （3b） and N-（4-bromobutanoyl）-N＇-（4- methylphenyl）thiourea （3c） were obtained in crystalline form by recrystallization from DMSO. X- ray crystallographic studies showed that both compounds 3b and 3c crystallize in triclinic system with space group ofPi. The molecules adopt trans-cis configuration with respect to the positions of 4-bromobutanoyl and tolyl groups respectively, against the thiono C=S bond across their C-N bonds The configuration is attributed by the intrahydrogen bond between the carbonyl oxygen and amide hydrogen atoms. Both crystal structures are stabilized by N-H…S intermolecular hydrogen bonds to form dimers and arranged along the b axis.展开更多
基金the Ministry of Higher Education of Malaysia and Universiti Kebangsaan Malaysia for the research grant DIP-2014-016 and FRGS/1/2013/ST01/UKM/03/4the Ministry of Higher Education of Libya for the scholarship
文摘N-4-（bromobutanoyl）-N＇-（o-, m- and p-tolyl）thioureas 3a, 3b and 3c respectively, were synthesized by the reaction of 4-bromobutanoylisothiocyanate with p-, m- and o-toludine. The products were characterized by IR, and NMR spectroscopic techniques. The two carbonoylthiourea isomers N-（4-bromobutanoyl）-N＇-（3-methylphenyl）thiourea （3b） and N-（4-bromobutanoyl）-N＇-（4- methylphenyl）thiourea （3c） were obtained in crystalline form by recrystallization from DMSO. X- ray crystallographic studies showed that both compounds 3b and 3c crystallize in triclinic system with space group ofPi. The molecules adopt trans-cis configuration with respect to the positions of 4-bromobutanoyl and tolyl groups respectively, against the thiono C=S bond across their C-N bonds The configuration is attributed by the intrahydrogen bond between the carbonyl oxygen and amide hydrogen atoms. Both crystal structures are stabilized by N-H…S intermolecular hydrogen bonds to form dimers and arranged along the b axis.
