Skip to main content
SpringerLink
Log in

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

  • Brief Communications
  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. R. H. Tale, A. T. Rodge, G. D. Hatnapure, and A. P. Keche, Bioorg. Med. Chem. Lett., 21, No. 15, 4648–4651 (2001).

    Article  Google Scholar 

  2. P. Cao, X.-F. Huang, H. Ding, H.-M. Ge, H.-Q. Li, B.-F. Ruan, and H.-L. Zhu, Chem. Biodiversity, 4, No. 5, 881–886, (2007).

    Article  CAS  Google Scholar 

  3. F. N.-F. How, K. A. Crouse, M. I. M. Tahir, M. T. H. Tarafder, and A. R. Cowley, Polyhedron, 27, No. 15, 3325–3329 (2008).

    Article  CAS  Google Scholar 

  4. S. T. Byrne, P. Gu, J. Zhou, S. M. Denkin, C. C. Chong, D. Sullivan, J. O. Liu, and Y. Zhang, Antimicrob. Agents Chemother., 51, No. 12, 4495–4497 (2007).

    Article  CAS  Google Scholar 

  5. Bruker. SAINT, SMART and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA (2007).

    Google Scholar 

  6. G. M. Sheldrick, Acta Crystallogr., A64, 112–122 (2008).

    Article  Google Scholar 

  7. Materials Modeling and Simulation Software, Release 4.3, Accelrys Software Inc., San Diego (2007).

  8. J. P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244–13249 (1992).

    Article  Google Scholar 

  9. S. Tayamon, T. B. S. A. Ravoof, M. I. M Tahir, K. A Crouse, and E. R. T. Tiekink, Acta Crystallogr., E68, o1640/o1641 (2012).

    Google Scholar 

  10. J. P. Jasinski, R. J. Butcher, S. K. Kushawaha, M. K. Bharty, and N. K. Singh, Acta Crystallogr., E66, o1899 (2010).

    Google Scholar 

  11. F. H. Allen, O Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1–S19 (1987).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Kulliyyah of Science, International Islamic University Malaysia, Jalan Sultan Ahmad Shah, Bandar Indera Mahkota, 25200, Kuantan, Pahang, Malaysia

    F. N.-F. How & N. Jamaluddin

  2. Department of Chemistry, Universiti Malaya, Kuala Lumpur, Malaysia

    S. N. Abdul Halim & V. S. Lee

Authors
  1. F. N.-F. How
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. Jamaluddin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. N. Abdul Halim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. S. Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to F. N.-F. How.

Additional information

Original Russian Text © 2015 F. N.-F. How, N. Jamaluddin, S. N. Abdul Halim, V. S. Lee.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1486-1491, November-December, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

How, F.NF., Jamaluddin, N., Abdul Halim, S.N. et al. Structure determination and tautomeric transition of 3-amino-1{[bis(benzylsulfanyl)methylidene]amino}urea. J Struct Chem 56, 1431–1436 (2015). https://doi.org/10.1134/S002247661507029X

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S002247661507029X

Keywords

Search

Navigation