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.
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Bruker. APEX2, SAINT and SAINT + (includes XPREP and SADABS). Bruker AXS Inc., Madison, WI, 2006.
Sheldrick GM. SHELXL97. Germany: University of Göttingen; 1997.
Sheldrick G. A short history of SHELX. Acta Cryst A. 2008;64(1):112–22.
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.
Mandelkern L. Crystallization of polymers. New York: Mcgraw-Hill; 1964.
Aly KI. New polymer syntheses VIII. Synthesis, characterization and morphology of new unsaturated copolyesters based on dibenzylidenecycloalkanones. Polym Int. 1998;47(4):483–90.
Pansuriya PB, Friedrich HB, Maguire GEM. 1,1′-(Ethane-1,2-diyl)bis(3-phenylthiourea). Acta Cryst E. 2011;67(11):o2819.
Pansuriya P, Friedrich HB, Maguire GEM. 3,3′-Diphenyl-1,1′-(butane-1,4-diyl)dithiourea. Acta Cryst E. 2011;67(9):o2380.
Pansuriya P, Naidu H, Friedrich HB, Maguire GEM. 1,1′-(Propane-1,3-diyl)bis(3-phenylurea). Acta Cryst E. 2011;67(10):o2552.
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.
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.
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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
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DOI: https://doi.org/10.1007/s10973-012-2309-3