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

• Main Authors: How, F.N.F., Jamaluddin, N., Halim, S.N.A., Lee, V.S.
• Format: Article
• Published: 2015
• Subjects: QD Chemistry
• Online Access: http://eprints.um.edu.my/16313/

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.