Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power

Organic and Biomolecular Chemistry

Volumn 2, Issue 24, 2004, Pages 3602-3607

  Giorgio, Egidio ^a   Parrinello, Nunziatina ^b   Caccamese, Salvatore ^b   Rosini, Carlo ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CORRELATION METHODS; EXCITONS; HYDROLYSIS; PHENOLS; POLYSACCHARIDES; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; PROPANE; STEREOCHEMISTRY;

ABSOLUTE CONFIGURATION (AC); CIRCULAR DICHROISM (CD); HETEROCYCLIC AMINES; NARINGIN;

AMINES;

FLAVANONE DERIVATIVE; NARINGENIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; ISOLATION AND PURIFICATION; OPTICAL ROTATION; STEREOISOMERISM;

CIRCULAR DICHROISM; FLAVANONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OPTICAL ROTATION; STEREOISOMERISM;

EID: 10944222281     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411110a     Document Type: Article

References (50)

1. W. L. Bear and R. W. Teel, Anticancer Res., 2000, 20, 3609.
2. F. V. So, N. Guthrie, A. F. Chambers, M. Moussa and K. K. Carroll, Nutr. Cancer, 1996, 26, 167.
3. M. A. Moroney, M. J. Alcaraz, R. A. Forder, F. Carey and J. R. S. Hoult, J. Pharm. Pharmacol., 1988, 40, 787.
4. R. Crossley, Tetrahedron., 1992, 48, 8155.
5. S. Caccamese, L. Manna and G. Scivoli, Chirality, 2003, 15, 661.
6. W. Gaffield, R. E. Lundin, B. Gentili and R. M. Horowitz, Bioorg. Chem., 1975, 4, 259.
7. W. Gaffield, Tetrahedron, 1970, 26, 4093.
8. (a) Treatments of the coupled-oscillator model and its application to organic stereochemistry can be found in:S. F. Mason, Q. Rev. Chem. Soc., 1963, 17, 20;
9. (b) S. F Mason, in Theory II in Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, ed. G. Snatzke, Wiley and Sons, London, 1967, ch. 4. p. 71;
10. (c) G. Gottarelli, S. F. Mason and G. Torre, J. Chem. Soc. B, 1971, 1349;
11. (d) E. Charney, in The Molecular Basis of Optical Activity Optical Rotatory Dispersion and Circular Dichroism, Wiley and Sons, New York, 1979;
12. (e) S. F. Mason, in Molecular Optical Activity and Chiral Discrimination, Cambridge University Press, Cambridge, 1982;
13. (f) Qualitative exciton treatments leading to simple chirality rules can be found in: N. Harada and K. Nakanishi, Acc. Chem. Res., 1972, 5, 257;
14. (g) N. Harada, K. Nakanishi in Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley CA, 1983;
15. (h) K. Nakanishi, N. Berova, in Circular Dichroism: Principles and Applications, ed. K. Nakanishi, N. Berova, R. W. Woody, VCH Publishers, New York, 1994, ch.13, p. 361;
16. (i) K. Nakanishi, N. Berova, in Circular Dichroism: Principles and Applications, ed. K. Nakanishi, N. Berova, R. W. Woody, Wiley-VCH Publishers, New York, 2000, ch. 12, p. 337.
17. (a) H. DeVoe, J.Chem.Phys. 1964, 41, 393;
18. (b) H. DeVoe, J.Chem.Phys. 1965, 43, 3199;
19. (c) C. Rosini, P. Salvadori and M. Zandomeneghi, Tetrahedron: Asymmetry, 1993, 4, 545;
20. (d) S. Superchi, E. Giorgio and C. Rosini, Chirality, 2004, 16, 422.
21. D has been carried out by Polavarapu; P. L. Polavarapu, Mol. Phys., 1997, 91, 551;
22. (b) R. K. Kondru, P. Wipf and D. N. Beratan, J. Am. Chem. Soc., 1998, 120, 2204;
23. (c) Stephens et al. did a systematic study about scope and limitation of this method: P. J. Stephens, F. J. Devlin, J. R. Cheeseman and M. J. Frisch, J. Phys. Chem. A, 2001, 105, 5356;
24. (d) All the papers which appeared on this subject have been recently reviewed: P. L. Polavarapu, Chirality, 2002, 14, 768.
25. D are: K. Takeshi, F. Miyako, H. Toshiyuki, C. Tominari, N. Junko, O. Yukio and H. Satoshi, Chem. Pharm. Bull., 2003, 51, 20;
26. (b)S. B. Vogensen, J. R. Greenwood, A. R. Varmin, L. Brehm, D. S. Pickering, B. Nielsen, T. Liljefors, R. P. Clausen, T. N. Johansen and P. Krogsgaard-Larsen, Org. Biomol. Chem., 2004, 2, 206.
27. For an explanation of these terms see: S. Allenmark, Chromatographic Enantioseparation: Methods and Applications, Ellis Horwood, Chichester, 2nd edn. 1991, p. 82.
28. S. Caccamese, C. Caruso, N. Parrinello and A. Savarino, J. Chromatogr., A, submitted for publication.
29. H. B. Klevens and J. Platt, in Survey of Vacuum Ultraviolet Spectra of Organic Compounds in Solution. Systematics of the electronic spectra of conjugated molecules: a source book, J. Wiley and Sons, ed. J. Platt, New York, USA, 1964, paper no. 10.
30. J. Del Bene and H. H. Jaffè, J. Chem Phys., 1968, 49, 1221.
31. (a) N. L. Allinger, J. Am. Chem. Soc. 1977, 99, 8127;
32. (b) N. L. Allinger, R. A. Kok and M. R. Imam, J. Comp. Chem. 1988, 9, 591;
33. (c) J.-H. Lii, S. Gallion, C. Bender, H. Wikstrom, N. L. Allinger, K. M. Flurchick and M. M. Teeter, J. Comput. Chem., 1989, 10, 503.
34. G. Snatzke, Angew. Chem., Int. Ed. Engl., 1979, 18, 363.
35. C. L. Cech, W. Hug and I. Tinoco, Jr., Biopolymers, 1976, 15, 131.
36. H. H. Jaffè, M. Orchin, in The Theory and Application of UV Spectroscopy, John Wiley and Sons, New York, 1962.
37. J. Sagiv, Tetrahedron, 1977, 33, 2303.
38. K. Shingu, S. Imaio, H. Kuritani, S. Hagishita and K. Kurijama, J. Am. Chem. Soc., 1983, 105, 6966.
39. G. Pescitelli, S. Gabriel, Y. Wang, J. Fleischhauer, R.W. Woody and N. Berova, J. Am. Chem. Soc., 2003, 125, 7613.
40. Gaussian98 and Gaussian03, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. F., Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J.A., Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashcnko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen,; M. W. Wong, J. L. Andres, M. Head-Gordon, H. S. Replogle, J. A. Pople, Gaussian, Inc.: Pittsburgh, PA.
41. DALTON, a molecular electronic structure program, Release 1.2 (2001), written by T. Helgaker, H. J. Aa. Jensen, P. Joergensen, J. Olsen, K. Ruud, H. Aagren, A.A. Auer, K.L. Bak, V. Bakken, O. Christiansen, S. Coriani, P. Dahle, E. K. Dalskov, T. Enevoldsen, B. Fernandez, C. Haettig, K. Hald, A. Halkier, H. Heiberg, H. Hettema, D. Jonsson, S. Kirpekar, R. Kobayashi, H. Koch, K. V. Mikkelsen, P. Norman, M. J. Packer, T. B. Pedersen, T. A. Ruden, A. Sanchez, T. Saue, S. P. A. Sauer, B. Schimmelpfennig, K. O. Sylvester-Hvid, P. R. Taylor, O. Vahtras.
42. R. Ahlrichs, M. Bar, H.-P. Baron, R. Bauernschmitt, S. Bocker, M. Ehrig, K. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Haser, H. Horn, C. Hattig, C. Huber, U. Huniar, M. Kattannek, A. Kohn, C. Kolmes, M. Kollwitz, K. May, C. Ochsenfeld, H. Öhm, A. Schafer, U. Schneider, O. Treutler, M. v. Arnim, F. Weigend, P. Weis, H. Weiss, TURBOMOLE, version 5.6; Universitat Karlsruhe, Karlsruhe, Germany, 2002.
43. (a) L. Rosenfeld, Z. Phys., 1928, 52, 161;
44. (b) E. U. Condon, Rev. Mod. Phys., 1937, 9, 432;
45. (c) A. D. Buckingham, Adv. Chem. Phys., 1967, 12, 107.
46. (a) E. Giorgio, C. Minichino, R. G. Viglione, R. Zanasi and C. Rosini, J. Org. Chem., 2003, 68, 5186;
47. (b) E. Giorgio, R. G. Viglione and C. Rosini, Tetrahedron: Asymmetry, 2004, 15, 1979.
48. P. J. Stephens, F. J. Devlin, J. R. Cheeseman, M. J. Frisch, O. Bortolini and P. Besse, Chirality, 2002, 14, 288.
49. See for instance, W. W. Wood, W. Fickett and J. G. Kirkwood, J. Chem. Phys., 1952, 20, 561.
50. W. Hug, F. Ciardelli and I. Tinoco, J. Am. Chem. Soc., 1974, 96, 3407.