Skip to main content
SpringerLink
Log in

Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

To the memory of Professor G.I. Koldobskii

Abstract

It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite layers normal to the c axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the b axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present.

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

Similar content being viewed by others

References

  1. Maly, R. Lieb. Ann. 1877, vol. 189, p. 380.

    Article  Google Scholar 

  2. Ray, P.C. and Fernandes, F.V. J. Chem. Soc., 1914, vol. 105, p. 2159.

    Article  CAS  Google Scholar 

  3. Desai, R.D., Hunter, R.F., and Koppar, L.G., Rec. Trav. Chim., 1935, vol. 54, p. 118.

    Article  CAS  Google Scholar 

  4. Lazarev, D.B., Ramsh, S.M., and Ivanenko, A.G., Zh. Org. Khim., 2000, vol. 70, p. 475.

    Google Scholar 

  5. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A. G., and Taylor, R., J. Chem. Soc., Perkin Trans. II, 1987, S1.

    Google Scholar 

  6. Brand, H., Hubrich, C., Polborn, K., Schulz, A., and Villinger, A., Acta Cryst., Sect. E: Struct. Rep. Online., 2007, 63, no. 12, o4733.

    Article  CAS  Google Scholar 

  7. Kushakova, P.M., Ramsh, S.M., and Garabadzhiu, A.V., Khim. Geterotsikl. Soedin., 2006, p. 250.

    Google Scholar 

  8. Roothaan, C.C., J. Rev. Mod. Phys., 1951, vol. 23, no. 2, p. 69.

    Article  CAS  Google Scholar 

  9. Stewart, J.J.P., J. Mol. Model., 2007, vol. 13, p. 1173.

    Article  CAS  Google Scholar 

  10. Mulliken, R.S., J. Chem. Phys., 1955, vol. 23, p. 1833.

    Article  CAS  Google Scholar 

  11. Pal’m, V.A., Vvedenie v teoreticheskuyu organicheskuyu khimiyu (Introduction on Theoretical Organic Chemistry), Moscow: Vysshaya Shkola, 1974, p. 168.

    Google Scholar 

  12. Altomare, A., Camalli, M., Cuocci, C., Giacovazzo, C., Moliterni, A., and Rizzi, R., J. Appl. Cryst., 2009, vol. 42, p. 1197.

    Article  CAS  Google Scholar 

  13. Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P.A., McCabe, P., Pidcock, E., Rodrigues-Monge, L., Taylor, R., van de Streek, J., and Wood, P.A., J. Appl. Cryst., 2008, vol. 41, p. 466.

    Article  CAS  Google Scholar 

  14. Stewart, J.J.P., Program package MOPAC2009. http://OpenMOPAC.net

  15. Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, p. 1347; http://molecularmodelingbasics.blogspot.com/search/label/gamess.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Technological Institute, St. Petersburg, 190013, Russia

    V. S. Fundamenskii, S. M. Ramsh, V. A. Brouskov & A. V. Smirnova

  2. Latvian Institute of Organic Synthesis, Riga, Russia

    A. Yu. Yanichev, M. B. Fleisher & S. V. Belyakov

Authors
  1. V. S. Fundamenskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. M. Ramsh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Brouskov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Smirnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. Yu. Yanichev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. B. Fleisher
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. V. Belyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. M. Ramsh.

Additional information

Original English Text © V.S. Fundamenskii, S.M. Ramsh, V.A. Brouskov, A.V. Smirnova, A.Yu. Yanichev, M. B. Fleisher, S.V. Belyakov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 5, pp. 690–696.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fundamenskii, V.S., Ramsh, S.M., Brouskov, V.A. et al. Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods. Russ J Org Chem 49, 672–677 (2013). https://doi.org/10.1134/S1070428013050060

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428013050060

Keywords

Search

Navigation