Comparison of calculated DFT/B3LYP and experimental 13C and 17O NMR chemical shifts, ab initio HF/6-31G* optimised structures, and single crystal X-ray structures of some substituted methyl 5β-cholan-24-oates

Journal of Molecular Structure

Volumn 650, Issue 1-3, 2003, Pages 201-212

  Virtanen, E ^a   Valkonen, A ^a   Tamminen, J ^a   Kolehmainen, E ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

13C and 17O NMR chemical shifts; Ab initio HF optimised structures; DFT GIAO; Substituted 5 cholan 24 oates; X ray structures

Indexed keywords

METHYL 3 OXO 5BETA CHOLAN 24 OATE; METHYL 3,12 DIOXO 5BETA CHOLAN 24 OATE; METHYL 3ALPHA HYDROXY 5BETA CHOLAN 24 OATE; METHYL 3BETA HYDROXY 5BETA CHOLAN 24 OATE; METHYL GROUP; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CRYSTALLIZATION; LINEAR REGRESSION ANALYSIS; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0038665440     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(03)00156-X     Document Type: Article

References (36)

1. R.E. Wasylishen, S. Mooibroek, J.B. Macdonald, J. Chem. Phys. 81 (1984) 1057.
2. L.L. Smith, J.E. Herz, E.L. Ezell, Steroids 58 (1993) 260.
3. E. Kolehmainen, M. Kaartinen, R. Kauppinen, J. Kotoneva, K. Lappalainen, P.T. Lewis, R. Seppälä, J. Sundelin, V. Vatanen, Magn. Reson. Chem. 32 (1994) 441.
4. H. Kählig, W. Robien, Magn. Reson. Chem. 32 (1994) 608.
5. M. Filowitz, R.K.C. Rao, W.G. Klemperer, W. Shum, Inorg. Chem. 18 (1979) 93.
6. I.P. Gerothanassis, Org. Magn. Reson. 21 (1983) 719.
7. J. Koivisto, E. Kolehmainen, V. Nikiforov, M. Nissinen, K. Tuppurainen, M. Peräkylä, S.A. Miltsov, V.S. Karavan, ARKIVOC iii (2001) 95.
8. P. Cmoch, B. Kamienski, K. Kamienska-Trela, L. Stefaniak, G.A. Webb, J. Phys. Org. Chem. 13 (2000) 480.
9. G. Cerioni, A. Plumitallo, F. Mocci, Z. Rappoport, M.B. Rubin, J. Chem. Soc., Perkin Trans. 2 (2001) 774.
10. I. Chao, K.-W. Chen, T.-S. Hwang, K.-T. Liu, J. Phys. Org. Chem. 14 (2001) 591.
11. E. Virtanen, M. Nissinen, R. Suontamo, J. Tamminen, E. Kolehmainen, J. Mol. Struct. 649 (2003) 207.
12. M. Sugahara, S. Kazuki, H. Junji, M. Miyata, Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 356 (2001) 155 and references cited therein.
13. D.A. Norton, B. Haner, Acta Cryst. 19 (1965) 478.
14. J.L. Scott, J. Chem. Soc., Perkin Trans. 2 (1995) 495.
15. U. Maitra, B.G. Bag, P. Rao, D. Powell, J. Chem. Soc., Perkin Trans. 1 (1995) 2049.
16. L.J. D'Souza, U. Maitra, J. Org. Chem. 61 (1996) 9494.
17. M. Akram, J.K. Denike, F. Belanger-Gariepy, X.-X. Zhu, Acta Cryst., Sect. C 52 (1996) 2905.
18. H. Liu, F. Belanger-Gariepy, M. Akram, M. Moskova, X.-X. Zhu, Acta Cryst., Sect. C 54 (1998) 801.
19. L.F. Fieser, S. Rajagopalan, J. Am. Chem. Soc. 72 (1950) 5530.
20. F.C. Chang, J. Org. Chem. 44 (1979) 4567.
21. D. Albert, M. Feigel, Tetrahedron Lett. 35 (1994) 565.
22. D. Albert, M. Feigel, Helv. Chim. Acta 80 (1997) 2168.
23. T. Iida, T. Tamura, T. Matsumoto, F.C. Chang, Yukagaku 32 (1983) 232.
24. J.R. Dias, H. Gao, E. Kolehmainen, Spectrochim. Acta A 56 (2000) 53 and references cited therein.
25. HyperChem™, Version 4.5 for Windows, Hypercube Inc., Waterloo, Canada, 1994.
26. N.L. Allinger, J. Am. Chem. Soc. 99 (1977) 8127.
27. N.L. Allinger, Y.H. Yuh, Quantum chemistry program exchange, Bloomington, Indiana, Program No. 395, molecular mechanics, in: U. Burkert, N.L. Allinger (Eds.), ACS Monograph 177, American Chemical Society, Washington, DC, 1982.
28. J.J.P. Stewart, J. Comput. Chem. 10 (1989) 209.
29. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. 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, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, 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. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN 98, Revision A.11, Gaussian, Inc., Pittsburgh, PA, 2001.
30. K. Wolinski, J.F. Hilton, P.J. Pulay, J. Am. Chem. Soc. 112 (1990) 8251.
31. E. Kolehmainen, J. Koivisto, V. Nikiforov, M. Peräkylä, K. Tuppurainen, K. Laihia, R. Kauppinen, S.A. Miltsov, V.S. Karavan, Magn. Reson. Chem. 37 (1999) 743.
32. Z. Otwinowski, W. Minor, in: C.W. Carter Jr., R.M. Sweet (Eds.), Macromolecular Crystallography, part A, Methods of Enzymology, vol. 276, Academic Press, New York, 1997, pp. 307-326.
33. G.M. Sheldrick, Acta Cryst. A46 (1990) 467.
34. G.M. Sheldrick, SHELXL-97™ A Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
35. L.J. Farrugia, J. Appl. Cryst. 30 (1997) 565.
36. M. Sorkin, T. Reichstein, Helv. Chim. Acta 27 (1944) 1631.