Structure determination and tautomeric transition of 3-amino-1{[bis(benzylsulfanyl)methylidene]amino}urea

• Main Authors: How, Fiona Ni Foong, Jamaluddin, N., Abdul Halim, S. N., Lee, V. S.
• Format: Article
• Language: English
• Published: Pleiades Publishing, Ltd. 2015
• Subjects: QD Chemistry
• Online Access: http://irep.iium.edu.my/46442/1/how2015.pdf; http://irep.iium.edu.my/46442/; http://www.springer.com/chemistry/inorganic+chemistry/journal/10947

The single crystal X-ray analysis of 3-amino-1{[bis(benzylsulfanyl)methylidene]amino}urea shows that the compound crystallizes in the triclinic system with the space group P-1 and Z = 4. The asymmetric unit contains two independent molecules of 3-amino-1{[bis(benzylsulfanyl)methylidene]amino}urea. Both bis(benzylsulfanyl)methylidene groups are in a trans configuration with respect to the C16/O1/N3/N4 and C32/O2/N7/N8 fragments, respectively. The tautomeric transition energies of the three tautomeric forms are calculated at the generalized gradient approximation (GGA) level by the BLYP/DND method to estimate the kinetic and thermodynamic barriers. The keto form has a lower energy than the other two forms. Relatively lower values of kinetic barriers (about 58 kcal/mol for the transition between (a) and (b) forms) are found.