Gülten KAVAK, Süheyla ÖZBEY, Gün BİNZET, Nevzat KÜLCÜ

Synthesis and single crystal structure analysis of three novel benzoylthiourea derivatives

N,N-dimethyl-N' -(2-methylbenzoyl)thiourea, C11H14N2SO (HL1), N,N-dibutyl-N' -(2-methylben\-zoyl)thiourea, C{17}H{26}N2SO (HL2), and N,N-dihexyl-N' -(2-methylbenzoyl) thiourea, C{21}H{34}N2SO (HL3) were synthesized and characterized by elemental analysis, spectroscopic methods (FT-IR, NMR), and single crystal X-ray diffraction. Compound HL1 crystallizes in the monoclinic system, space group P21/c, Z = 4. Compound HL3 also crystallizes in the monoclinic system, space group P21/n, Z = 8 with 2 independent molecules in the asymmetric unit. Compound HL2 crystallizes in the orthorhombic system, space group Pcnn, Z = 8. In all compounds, molecules form dimers through the strong intermolecular N-H...S hydrogen bonds. Moreover, there are different types of intra- and inter-molecular interactions in the crystal structures, and so the molecules of the 3 compounds also pack differently.

Anahtar Kelimeler:

Thiourea derivatives, benzoylthioureas, single crystal X-ray structures.

Synthesis and single crystal structure analysis of three novel benzoylthiourea derivatives

Keywords:

Thiourea derivatives, benzoylthioureas, single crystal X-ray structures.,

PDF

___

1. Neucki, E. Ber 6. 1873, 598.
2. Beyer, L.; Hoyer, E.; Hartman, H.; Liebscher, J. Z. Chem. 1981, 21, 81-91.
3. M¨uhl, P.; Gloe, K.; Dietze, F.; Hoyer, E.; Beyer, L. Z. Chem. 1986, 26, 81-94.
4. K¨onig, K. H.; Schuster, M.; Steinbrech, B.; Schneeweis, G.; Schodder, R.; Fresenius, Z. Anal. Chem. 1985, 321, 457-460.
5. Vest, P.; Schuster, M.; K¨onig, K. H.; Fresenius, Z. Anal. Chem. 1991, 341, 566-568.
6. Burrows, D. A.; Mare, D.C. ; Mahon, F.M. Polyhedron 1999, 18, 2665-2671.
7. Henderson, W.; Nicholson, B. K.; Dinger, M. B.; Bennett, R. L. Inorg. Chim. Acta. 2002, 338, 210-218.
8. Campo, R.; Criado, J. J.; Gheorghe, R.; Gonzalez, F. J.; Hermosa, M. R.; Sanz, F.; Manzano, J. L.; Monte, E.; Fernandez, E. R. J. Inorg. Biochem. 2004, 98, 1307-1314.
9. Shen, X.; Shi, X.; Kang, B.; Liu, Y.; Tong, Y.; Jiang H.; Chen, K. Polyhedron 1988, 17, 4049-4058.
10. French, F. A.; Blanz, E. J.; Amaral, J. R. D.; French, D. A. J. Med. Chem. 1970, 13, 1117-1124.
11. Mohapatra, B. B.; Guru, S.; Mohapatra, K. B. J. Inorg. Nul. Chem. 1977, 39, 2291-2292.
12. Antholine, W.; Taketa, F. J. Inorg. Biochem. 1982, 16, 145-154.
13. Huebhr, O. F.; Marsh, J. L.; Mizzoni, R. H.; Mull, R. P.; Schroeder, D. C.; Troxell, H. A.; Scholz, C. R. J. Am. Chem. Soc. 1953, 75, 2274-2275.
14. Madan, V. K.; Taneja, A. D. Indian Chem. Soc. 1991, 68, 471-472.
15. French, F. A.; Blanz, E. J. Cancer Res. 1965, 25, 1454-1458.
16. Blanz, E. J.; French, F. A. Cancer Res. 1965, 28, 2419-2422.
17. French, F. A.; Blanz, E. J. J. Med. Chem. 1966, 9, 585-589.
18. Fernandes, E. R.; Manzano J. L.; Benito, J. J.; Hermosa, R.; Monte, E.; Criado, J. J. Journal of Inorganic Biochemistry 2005, 99, 1448-1572.
19. Binzet, G. PhD thesis (unpublished work), Mersin University. 20. Douglass, I. B.; Dains, F. B. J. Am. Chem. Soc. 1934, 56, 719.
21. Sheldrick, G. M. SHELXS-97, SHELXL-97 Program for crystal structure solution and refinement. University of Gottingen, G¨ottingen, Germany 1997.
22. Binzet, G.; Arslan, H.; Florke, U.; Kulcu, N.; Duran, N. J. Coord. Chem. 2006, 59, 1395-1406.
23. Arslan, H.; Fl¨orke, U.; K¨ulc¨u, N. J. Chem. Crystallogr. 2003, 33, 919-924.
24. Reichardt, C. Solvent and Solvent Effects in Organic Chemistry, second ed., VCH, Weinheim, 1988.
25. Arslan, H.; Fl¨orke, U.; K¨ulc¨u, N. Turk. J. Chem. 2004, 28, 673-678.
26. Arslan, H.; Fl¨orke, U.; K¨ulc¨u, N. Acta Cryst. 2003, E59, o641-o642.
27. Saeed, A.; Parvez, M. Central European J. Chem. 2005, 3(4), 780-791.
28. Arslan, H.; K¨ulc¨u, N.; Fl¨orke, U. Spectrochimica Acta Part A 2006, 64, 1065-1071.
29. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc. Perkin Trans, 2 1987, 12, S1-S9.
30. Khawar, R. M.; Badshah, A.; Bolte, M. Acta Cryst. 2007, E63, o1679-o1680.
31. Shanmuga, S. R. S.; Puviarasan, K.; Velmurugan, D.; Fun, K. F. Acta Cryst. 1999, C55, 1318-1320.