Optical activity of benzophenone and thiobenzophenone generated by spontaneous crystallization and inclusion complexation with cholic acid

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 103-107

  Szyrszyng, Monika ^a   Nowak, Elzbieta ^b,c   Gdaniec, Maria ^b   Milewska, Maria J ^a   Połoński, Tadeusz ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

^c EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' DIMETHYLBENZOPHENONE; BENZOPHENONE; BENZOPHENONE DERIVATIVE; CHOLIC ACID; KETONE; THIOBENZOPHENONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; COMPLEX FORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENERGY; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0348048756     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.019     Document Type: Article

References (44)

1. (a) Green B.S., Lahav M., Rabinovich D. Acc. Chem. Res. 12:1979;191
2. (b) Sakamoto M. Chem. Eur. J. 3:1997;684
3. (c) Ito Y. Synthesis. 1998;1
4. (d) Tanakam K., Toda F. Chem. Rev. 100:2000;1025.
5. (a) Jacques J., Collet A., Wilen S.M. Enantiomers, Racemates, and Resolutions. 1981;Wiley, New York, Eliel E., Wilen S.H. Stereochemistry of Organic Compounds. 1994;Wiley, New York. Chapter 7.2.
6. (a) Jacques J., Collet A., Wilen S.M. Enantiomers, Racemates, and Resolutions. 1981;Wiley, New York, Eliel E., Wilen S.H. Stereochemistry of Organic Compounds. 1994;Wiley, New York. Chapter 7.2.
7. (a) Iitaka Y. Acta Cryst. 11:1958;225
8. (b) Shimon L.J.W., Lahav M., Leiserowitz L. New J. Chem. 10:1986;723.
9. (a) Brown C.J., Sadanaga R. Acta Cryst. 18:1965;158
10. (b) More M., Odou G., Lefebvre J. Acta Cryst. B43:1987;398.
11. Połoński T., Szyrszyng M., Gdaniec M., Nowak E., Herman A. Tetrahedron: Asymmetry. 12:2001;797.
12. (a) Wilson K.R., Pincock R.E. J. Am. Chem. Soc. 97:1975;1474
13. (b) Kondepundi D.K., Laudadio J., Asakura K. J. Am. Chem. Soc. 121:1999;1448.
14. Cunningham I.D., Coles S.J., Hursthouse M.B. Chem. Commun. 2000;61.
15. Feringa B.L., van Delden R.A. Angew. Chem., Int. Ed. 38:1999;3419.
16. (a) Addadi L., Lahav M. Walker D.C. Origins of Optical Activity in Nature. 1979;Elsevier, Amsterdam. Chapter 14
17. (b) Buschmann H., Thede R., Heller D. Angew. Chem., Int. Ed. 39:2000;4033.
18. Gdaniec M., Połoński T. J. Am. Chem. Soc. 120:1998;7353
19. (b) Gdaniec M., Milewska M.J., Poloński T. Angew. Chem., Int. Ed. 38:1999;392
20. (c) Szyrszyng M., Nowak E., Gdaniec M., Milewska M.J., Herman A., Poloński T. J. Org. Chem. 66:2001;7380.
21. (a) Olszewska T., Milewska M.J., Gdaniec M., Poloński T. Chem. Commun. 1999;1385
22. (b) Olszewska T., Milewska M.J., Gdaniec M., Maluszyńska H., Poloński T. J. Org. Chem. 66:2001;501.
23. Fleisher E.B., Sung N., Hawkinson S. J. Phys. Chem. 72:1968;4311.
24. (a) Ito Y., Matsuura T., Tabata K., Ii-bun M., Fukuyama K., Sasaki M., Okada S. Tetrahedron. 43:1987;1307
25. (b) Kojic-Prodic B., Bresciani-Pahor N., Horvatic D. Acta Crystallogr. C46:1990;430.
26. Kutzke H., Al.-Mansour M., Klapper H. J. Mol. Struct. 374:1996;129.
27. (a) Bosnich B. J. Am. Chem. Soc. 89:1967;6143
28. (b) Matsuura N., Takenaka S., Tokura N. J. Chem. Soc., Perkin Trans. 2. 1977;1419
29. (c) Schipper P.E., O'Brien J.M., Ridley D.D. J. Phys. Chem. 89:1985;5805.
30. Maciejewski A., Steer R.P. Chem. Rev. 93:1993;67.
31. Scheeren J.W., Ooms P.H.J., Nivard R.J.F. Synthesis. 1973;149.
32. Nakano K., Sada K., Miyata M. Chem. Lett. 1994;137.
33. (a) Abraham R.J., Haworth I.S. J. Chem. Soc., Perkin Trans. 2. 1988;1429
34. (b) Rappoport Z., Biali S.E., Kaftory M. J. Am. Chem. Soc. 112:1990;7742.
35. Snatzke G., Snatzke F. Ciardelli F., Salvadori P. Fundamental Aspects and Recent Developments in Optical Rotatory Dispersion and Circula Dichroism. 1973;Heyden, London. Chapter 3.2 and references cited therein.
36. Miyata M., Sada K. Comprehensive Supramolecular Chemistry. MacNicol D.D., Toda F., Bishop R. Comprehensive Supramolecular Chemistry. Vol. 6, Chapter 6:1996;Pergamon, Oxford.
37. Nowak E., Gdaniec M., Poloński T. J. Incl. Phenom. 37:2000;155.
38. Rindorf G., Carlsen L. Acta Crystallogr. B35:1979;1179.
39. (a) Emeis C.A., Oosterhoff L.J. J. Chem. Phys. 54:1971;4809
40. (b) Engelbrecht J.P., Anderson G.D., Linder R.E., Barth G., Bunnenberg E., Djerassi C., Seamans L., Moscowitz A. Spectrochim. Acta. A31:1975;507
41. (c) Szymanski M., Maciejewski A., Steer R.P. J. Phys. Chem. 92:1988;2485
42. (d) Lightner D.A., Bouman T.D., Wijekoon W.M.D., Hansen A.E. J. Am. Chem. Soc. 112:1990;7742.
43. Sheldrick G.M. Acta Crystallogr. A46:1990;467.
44. Sheldrick, G. M. SHELXL-97, Program for Crystal Structures Refinement from Diffraction Data, University of Göttingen, Germany, 1997.