Skip to main content
Log in

Bisthiourea: thermal and structural investigation

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

Bisthiourea derivatives 1,1′-(ethane-1,2-diyl)bis(3-phenylthiourea), 1,1′-(propane-1,3-diyl)bis(3-phenylthiourea), and 1,1′-(butane-1,4-diyl)bis(3-phenylthiourea) have been synthesized and characterized by IR, 1H NMR, and 13C NMR. Suitable crystals of 1,1′-(propane-1,3-diyl)bis(3-phenylthiourea) were grown for single-crystal X-ray analysis and from the data it was observed that they organize into the P-1 space group. The thermal decomposition of these compounds has been studied by TG–DSC.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

References

  1. Wittkopp A, Schreiner PR. Metal-free, noncovalent catalysis of Diels–Alder reactions by neutral hydrogen bond donors in organic solvents and in water. Chem Eur J. 2003;9(2):407–14.

    Article  CAS  Google Scholar 

  2. Li X, Deng H, Luo S, Cheng J-P. Organocatalytic three-component reactions of pyruvate, aldehyde and aniline by hydrogen-bonding catalysts. Eur J Org Chem. 2008;25:4350–6.

    Article  Google Scholar 

  3. Sharma SK, Wu Y, Steinbergs N, Crowley ML, Hanson AS, Casero RA, et al. (Bis)urea and (Bis)thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators. J Med Chem. 2010;53(14):5197–212.

    Article  CAS  Google Scholar 

  4. Abdallah R, Breuzard JAJ, Bonnet MC, Lemaire M. Phosphite and thiourea ligand synergy for rhodium catalyzed enantioselective hydroformylation of styrene. J Mol Catal A. 2006;249(1–2):218–22.

    CAS  Google Scholar 

  5. Karamé I, Lorraine Tommasino M, Lemaire M. N, N- and N, S-ligands for the enantioselective hydrosilylation of acetophenone with iridium catalysts. J Mol Catal A. 2003;196(1–2):137–43.

    Google Scholar 

  6. Nan Y, Miao H, Yang Z. A new complex of palladium–thiourea and carbon tetrabromide catalyzed carbonylative annulation of o-hydroxylarylacetylenes: efficient new synthetic technology for the synthesis of 2,3-disubstituted benzo[b]furans. Org Lett. 2000;2(3):297–9.

    Article  CAS  Google Scholar 

  7. Breuzard JAJ, Tommasino ML, Touchard F, Lemaire M, Bonnet MC. Thioureas as new chiral ligands for the asymmetric hydroformylation of styrene with rhodium(I) catalysts. J Mol Catal A. 2000;156(1–2):223–32.

    CAS  Google Scholar 

  8. Park J, Lang K, Abboud KA, Hong S. Self-assembly approach toward chiral bimetallic catalysts: bis-urea-functionalized (salen)cobalt complexes for the hydrolytic kinetic resolution of epoxides. Chem Eur J. 2011;17(7):2236–45.

    Article  CAS  Google Scholar 

  9. Tommasino ML, Casalta M, Breuzard JAJ, Lemaire M. Asymmetric hydrogenation of enamides with catalysts containing chiral thiourea ligands. Tetrahedron Asymmetry. 2000;11(24):4835–41.

    Article  CAS  Google Scholar 

  10. Reinoso García MM, Verboom W, Reinhoudt DN, Malinowska E, Pietrzak M, Wojciechowska D. Heavy metal complexation by N-acyl(thio)urea-functionalized cavitands: synthesis, extraction and potentiometric studies. Tetrahedron. 2004;60(49):11299–306.

    Article  Google Scholar 

  11. Leung AN, Degenhardt DA, Bühlmann P. Effect of spacer geometry on oxoanion binding by bis- and tetrakis-thiourea hosts. Tetrahedron. 2008;64(11):2530–6.

    Article  CAS  Google Scholar 

  12. Ahmed N, Geronimo I, Hwang I-C, Singh NJ, Kim KS. Cyclo-bis(urea-3,6-dichlorocarbazole) as a chromogenic and fluorogenic receptor for anions and a selective sensor of zinc and copper cations. Chem Eur J. 2011;17(31):8542–8.

    Article  CAS  Google Scholar 

  13. Vos MRJ, Leclere PELG, Meekes H, Vlieg E, Nolte RJM, Sommerdijk NAJM. Kinetic switching between two modes of bisurea surfactant self-assembly. Chem Commun. 2010;46(33):6063–5.

    Article  CAS  Google Scholar 

  14. Dawn S, Dewal MB, Sobransingh D, Paderes MC, Wibowo AC, Smith MD, et al. Self-assembled phenylethynylene bis-urea macrocycles facilitate the selective photodimerization of coumarin. J Am Chem Soc. 2011;133(18):7025–32.

    Article  CAS  Google Scholar 

  15. Mariappan M, Madhurambal G, Ravindran B, Mojumdar S. Thermal, FTIR and microhardness studies of bisthiourea-urea single crystal. J Therm Anal Calorim. 2011;104(3):915–21.

    Article  CAS  Google Scholar 

  16. Ramamurthi K, Madhurambal G, Ravindran B, Mariappan M, Mojumdar S. The growth and characterization of a metal organic crystal, potassium thiourea thiocyanide. J Therm Anal Calorim. 2011;104(3):943–7.

    Article  CAS  Google Scholar 

  17. Madhurambal G, Mariappan M, Ravindran B, Mojumdar S. Thermal and FTIR spectral studies in various proportions of urea thiourea mixed crystal. J Therm Anal Calorim. 2011;104(3):885–91.

    Article  CAS  Google Scholar 

  18. Bruker. APEX2, SAINT and SAINT + (includes XPREP and SADABS). Bruker AXS Inc., Madison, WI, 2006.

  19. Sheldrick GM. SHELXL97. Germany: University of Göttingen; 1997.

    Google Scholar 

  20. Sheldrick G. A short history of SHELX. Acta Cryst A. 2008;64(1):112–22.

    Article  Google Scholar 

  21. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H. OLEX2: a complete structure solution, refinement and analysis program. J Appl Cryst. 2009;42(2):339–41.

    Article  CAS  Google Scholar 

  22. Mandelkern L. Crystallization of polymers. New York: Mcgraw-Hill; 1964.

    Google Scholar 

  23. Aly KI. New polymer syntheses VIII. Synthesis, characterization and morphology of new unsaturated copolyesters based on dibenzylidenecycloalkanones. Polym Int. 1998;47(4):483–90.

    Article  CAS  Google Scholar 

  24. Pansuriya PB, Friedrich HB, Maguire GEM. 1,1′-(Ethane-1,2-diyl)bis(3-phenylthiourea). Acta Cryst E. 2011;67(11):o2819.

    Article  Google Scholar 

  25. Pansuriya P, Friedrich HB, Maguire GEM. 3,3′-Diphenyl-1,1′-(butane-1,4-diyl)dithiourea. Acta Cryst E. 2011;67(9):o2380.

    Article  Google Scholar 

  26. Pansuriya P, Naidu H, Friedrich HB, Maguire GEM. 1,1′-(Propane-1,3-diyl)bis(3-phenylurea). Acta Cryst E. 2011;67(10):o2552.

    Article  Google Scholar 

  27. Roviello A, Sirigu A. Poly[oxytetradecanedioyloxy-1,4-phenylene-(2-methylvinylene)-1,4-phenylene]. A polymer showing monotropic mesomorphism. Die Makromol Chem. 1979;180(10):2543–5.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors wish to thank Dr. Hong Su from the Chemistry Department of the University of Cape Town and Dr. Manuel Fernandes from the Chemistry Department of the University of the Witwatersrand for their assistance with the X-ray data collection and refinement and the DST—National Research Foundation, Centre of Excellence in Catalysis, c*change, for financial support. PBP would like to thank UKZN for funding his post-doctorate fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Glenn E. M. Maguire.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pansuriya, P.B., Parekh, H.M., Friedrich, H.B. et al. Bisthiourea: thermal and structural investigation. J Therm Anal Calorim 111, 597–603 (2013). https://doi.org/10.1007/s10973-012-2309-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-012-2309-3

Keywords

Navigation