The conformational equilibrium of N,N'-bis[(S)-1-phenylethyl]-thiourea and its solvent dependence, studied by NMR and CD spectra and by X-ray crystallography

Canadian Journal of Chemistry

Volumn 76, Issue 6, 1998, Pages 811-820

  Rang, Knut ^a   Sandström, Jan ^a   Svensson, Christer ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

Circular dichroism; Conformation; Crystal structure; Dynamic NMR spectroscopy; N,N' bis (S) 1 phenylethyl thiourea

Indexed keywords

N,N' BIS(1 PHENYLETHYL)THIOUREA; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE; PREDICTION; SOLUBILITY; ULTRAVIOLET RADIATION; X RAY CRYSTALLOGRAPHY;

EID: 0031791479     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjc-76-6-811     Document Type: Article

References (58)

1. V.V. Dunina, E.G. Rukhadze, and A.P. Terent'ev. Zh. Obshch. Khim. 40, 2278 (1970); J. Gen. Chem. U.S.S.R. 2266 (1971).
2. V.V. Dunina, E.G. Rukhadze, and A.P. Terent'ev. Zh. Obshch. Khim. 40, 2278 (1970); J. Gen. Chem. U.S.S.R. 2266 (1971).
3. V.V. Dunina, E.G. Rukhadze, and A.P. Terent'ev. Zh. Obshch. Khim. 40, 2285 (1970); J. Gen. Chem. U.S.S.R. 2273 (1971).
4. V.V. Dunina, E.G. Rukhadze, and A.P. Terent'ev. Zh. Obshch. Khim. 40, 2285 (1970); J. Gen. Chem. U.S.S.R. 2273 (1971).
5. S. Mizushima. In Structure of molecules and internal rotation. Academic Press, New York. 1954. p. 118.
6. L. La Planche and M. Rogers. J. Am. Chem. Soc. 86, 337 (1964).
7. J. Sandström and B.Uppström. Acta Chem. Scand. 21, 2254 (1967).
8. R.H. Sullivan and E. Price. Org. Magn. Reson. 7, 143 (1975).
9. W. Walter and K.-P. Ruess. Justus Liebigs Ann. Chem. 746, 54 (1971).
10. U. Berg, T. Liljefors, C. Roussel, and J. Sandström. Acc. Chem. Res. 18, 80 (1985).
11. U. Berg and J. Sandström. Adv. Phys. Org. Chem. 25, 1 (1989).
12. M. Langgård and J. Sandström. J. Chem. Soc. Perkin Trans. 2, 435 (1996).
13. J.M. Lovén and E. Ohlsson. Ber. 47, 1534 (1914).
14. S. Kallenberg. Ber. 52, 2057 (1919).
15. K. Rang, F.-L. Liao, J. Sandström, and S.-L. Wang. Chirality, 9, 568 (1997).
16. SMART Software Reference Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, U.S.A. 1996.
17. SAINT Software Reference Manual. Siemens Analytical X-ray-Instruments Inc., Madison, Wisconsin, U.S.A. 1996.
18. U. Burkert and N.L. Allinger. In Molecular mechanics. ACS Monograph 177. American Chemical Society, Washington, D.C. 1982.
19. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart. J. Am. Chem. Soc. 107, 3902 (1985).
20. I. Pettersson and J. Sandström. Acta Chem. Scand. Ser. B, 38, 397 (1984).
21. C. Guimon, D. Gombeau, and G. Pfister-Guillouzo. Tetrahedron, 29, 3399 (1973).
22. K. Nishimoto and N. Mataga. Z. Phys. Chem. (Munich), 12, 335 (1957).
23. P.M. Bayley, E.B. Nielsen, and J.A. Schellman. J. Phys. Chem. 8, 228 (1969).
24. E.B. Nielsen and J.A. Schellman. Biopolymers, 10, 1559 (1971).
25. V. Madison and J.A. Schellman. Biopolymers, 11, 1041 (1972).
26. V. Rizzo and J.A. Schellman. Biopolymers, 23, 435 (1984).
27. E.U. Condon, W. Altar, and H. Eyring. J. Chem. Phys. 5, 753 (1937).
28. I. Tinoco, Jr. Adv. Chem. Phys. 4, 113 (1962).
29. J.A. Schellman. Acc. Chem. Res. 1, 144 (1968).
30. J.G. Kirkwood. J. Chem. Phys. 5, 479 (1937).
31. N. Harada and K. Nakanishi. In Circular dichroic spectroscopy - exciton coupling in organic stereochemistry. Oxford University Press, Oxford. 1983.
32. J. Sandström. In Circular dichroism, principles and applications. Edited by K. Nakanishi, N. Berova, and R.W. Woody. VCH Publishers, New York. 1994. p. 443.
33. L. Fernholt, S. Samdal, and R. Seip. J. Mol. Struct. 72, 217 (1981).
34. J. Roschester, U. Berg, M. Pierrot, and J. Sandström. J. Am. Chem. Soc. 109, 492 (1987).
35. M.M. Elcombe and J.C. Taylor. Acta Crystallogr. Sect. A: Cryst. Phys. Diffr. Theor. Gen. Crystallogr. A24, 410 (1968)
36. A. Ramnathan, K. Sivakumar, K. Subramanian. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. C51, 2446 (1995).
37. A. Ramnathan, K. Sivakumar, K. Subramanian, N. Janarthanan, K. Ramadas, and H.-K. Fun. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. C52, 134 (1996).
38. A. Ramnathan, K. Sivakumar, K. Subramanian, D. Merarani, and H.-K. Fun. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. C52, 139 (1996).
39. W. Walter, E. Schaumann, and H. Paulsen. Justus Liebigs Ann. Chem. 727, 61 (1969).
40. C. Roussel, A. Lidén, M. Chanon, J. Metzger, and J. Sandström. J. Am. Chem. Soc. 98, 2847 (1976).
41. A. Lidén, C. Roussel, T. Liljefors, M. Chanon, R.E. Carter, J. Metzger, and J. Sandström. J. Am. Chem. Soc. 98, 2853 (1976).
42. M. Barfield and H.L. Gearhart. J. Am. Chem. Soc. 95, 641 (1973).
43. V.F. Bystrov, V.T. Ivanov, S.L. Portnov, T.A. Balashova, and Yu.A. Ovchinnikov. Tetrahedron, 29, 873 (1974).
44. A. Demarco, M. Llinás, and K. Wütrich. Biopolymers, 17, 637 (1978).
45. J. Sandström. In Dynamic NMR spectroscopy. Academic Press, New York. 1982. p. 86.
46. C.D. Freeman and D.L. Hooper. J. Phys. Chem. 78, 961 (1974).
47. W. Walter and K.-P. Ruess. Justus Liebigs Ann. Chem. 743, 167 (1971).
48. V.V. Dunina, E.G. Rukhadze, and A.P. Terent'ev. Zh. Obshch. Khim. 42, 2565 (1972); J. Gen. Chem. U.S.S.R. 2556 (1973).
49. V.V. Dunina, E.G. Rukhadze, and A.P. Terent'ev. Zh. Obshch. Khim. 42, 2565 (1972); J. Gen. Chem. U.S.S.R. 2556 (1973).
50. M. Kajtar, M. Hollosi, J. Kajtar, Z. Majer, and A. Vass-Lakatos. In F.E.C.S. Int. Conf. Circular Dichroism. Sofia, Bulgaria. Sept. 21-25, 1985. p. 126.
51. M. Hollosi, Z. Majer, M. Zewdu, F. Ruff, M. Kajtar, and K.E. Köver. Tetrahedron, 44, 195 (1988).
52. M.J. Janssen. Rec. Trav. Chim. 79, 454 (1960).
53. M.J. Janssen. Rec. Trav. Chim. 79, 1066 (1960).
54. H. Hosoya, J. Tanaka, and S. Nagakura. Bull. Chem. Soc. Jpn. 33, 850 (1960).
55. R.K. Gosavi and C.N.R. Rao. Can. J. Chem. 45, 1897 (1967).
56. R.K. Ritchie and H. Spedding. Spectrochim. Acta Part A, 26A, 9 (1970).
57. J.R.J. Platt. J. Chem. Phys. 17, 484 (1949).
58. Z. Krawczyk and C. Belzecki. Pol. J. Chem. 53, 631 (1979).