Modeling NMR parameters by DFT methods as an aid to the conformational analysis of cis-fused 7a(8a)-methyl octa(hexa)hydrocyclopenta[d][1,3]oxazines and [3,1]benzoxazines

Journal of the American Chemical Society

Volumn 125, Issue 15, 2003, Pages 4609-4618

  Tähtinen, Petri ^a   Bagno, Alessandro ^b   Klika, Karel D ^a   Pihlaja, Kalevi ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DISCRETE FOURIER TRANSFORMS; NUCLEAR MAGNETIC RESONANCE; PROTONS;

CHEMICAL SHIFTS;

KETONES;

7A METHYLHEXAHYDROCYCLOPENTA[D][1,3]OXAZINE; 7A METHYLOCTAHYDROCYCLOPENTA[D][1,3]OXAZINE; 8A METHYLHEXAHYDRO[1,3]BENZOXAZINE; 8A METHYLHEXAHYDROCYCLOPENTA[D][3,1]BENZOXAZINE; 8A METHYLOCTAHYDROCYCLOPENTA[D][3,1]BENZOXAZINE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; ENERGY; GEOMETRY; NUCLEAR MAGNETIC RESONANCE; PROTEIN ANALYSIS; PROTEIN CONFORMATION; STEREOCHEMISTRY; TEMPERATURE;

EID: 0037448915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021237t     Document Type: Article

References (57)

1. Helgaker, T.; Jaszuński, M.; Ruud, K. Chem. Rev. 1999, 99, 293.
2. Fukui, H.; Baba, T. Nucl. Magn. Reson. 2002. 31, 122.
3. Fukui, H. Prog. Nucl. Magn. Reson. Spectrosc. 1999, 35, 267.
4. Bagno, A. Chem. Eur. J. 2001, 7, 1652.
5. Barone, G.; Gomez-Paloma, L.; Duca, D.; Silvestri, A.; Riccio, R.; Bifulco, G. Chem. Eur. J. 2002, 8, 3233.
6. Cloran, F.; Carmichael, I.; Serianni, A. S. J. Phys. Chem. A 1999. 103, 3783.
7. Cloran, F.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 1999, 121, 9843.
8. Cloran, F.; Carmichael, I.: Serianni, A. S. J. Am. Chem. Soc. 2001, 123, 4781.
9. Stenutz. R.; Carmichael, I.; Widmalm, G.; Serianni, A. S. J. Org. Chem. 2002, 67, 949.
10. Serianni, A. S.; Wu, J.; Carmichael, I. J. Am. Chem. Soc. 1995, 117, 8645.
11. Malkina, O. L.; Hricovíni, M.; Bízik, F.; Malkin, V. G. J. Phys. Chem. A 2001. 105, 9188.
12. Cloran, F.; Zhu, Y.; Osborn, J.; Carmichael, I.; Serianni, A. S. J. Am. Chem. Soc. 2000, 122, 6435.
13. Esteban, A. L.; Galache, M. P.; Mora, F.; Díez, E.; Casanueva, J.; Fabián, J. S.; Barone, V.; Peralta, J. E.; Contreras, R. H. J. Phys. Chem. A 2001, 105, 5298.
14. Wilkens, S. J.; Westler, W. M.; Markley, J. L.; Weinhold, F. J. Am. Chem. Soc. 2001, 123, 12 026.
15. Stahl, M.; Schopfer, U.; Frenking, G.; Hoffmann, R. W. J. Org. Chem. 1997, 62, 3702.
16. Perera, S. A.; Bartlett, R. J. Magn. Reson. Chem. 2001, 39, S183.
17. Case, D. A.; Scheurer, C.; Brüschweiler, R. J. Am. Chem. Soc. 2000, 122, 10 390.
18. Tähtinen, P.; Sinkkonen, J.; Klika, K. D.; Nieminen, V.; Stájer, G.; Szakonyi, Z.; Fülöp, F.; Pihlaja, K. Chirality 2002, 14, 187.
19. Fülöp, F.; Bernáth, G.; Pihlaja, K. Adv. Hererocycl. Chem. 1998, 69, 349.
20. Stájer, G.; Szabó, A. E.; Fülöp, F.; Bernáth, G.; Sohár, P. Heterocycles 1982, 19, 1191.
21. Stájer, G.; Szabó, A. E.; Fülöp, F.; Bernáth, G.; Kálmán, A.; Argay, G.; Sohár, P. Tetrahedron 1983, 39, 1829.
22. Bernáth, G.; Fülöp, F.; Kálmán, A.; Argay, G.; Sohár, P.; Pelczer, I. Tetrahedron 1984, 40, 3587.
23. Pihlaja, K.; Mattinen, J.; Bernáth, G.; Fülöp, F. Magn. Reson. Chem. 1986, 24, 145.
24. Pihlaja, K.; Mattinen, J.; Fülöp, F. Magn. Reson. Chem. 1996, 34, 998.
25. Szakonyi, Z.; Fülöp, F.; Bernáth, G.; Evanics, F.; Riddell, F. G. Tetrahedron 1998, 54, 1013.
26. Shaikhutdinov, R. A.; Klika, K. D.; Fülöp, F.; Pihlaja, K. Magn. Reson. Chem. 2001, 39, 141.
27. Danilova, O. I.; Samitov, Y. Y.; Boiko, I. P.; Yakusheva, A. D.; Unkovskii, B. V. Zh. Org. Khim. 1984, 20, 2323.
28. HyperChem Releases 4.5 and 7 for Windows, Hypercube Inc.
29. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
30. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J, A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
32. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
34. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
35. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
36. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. In Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
37. nd Ed.; Gaussian Inc.: Pittsburgh, PA, 1996; p 64.
38. Barone, G.; Duca, D.; Silvestri, A.; Gomez-Paloma, L.; Riccio, R.; Bifulco, G. Chem. Eur. J. 2002, 8, 3240.
39. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796.
40. Bagno, A. Chem. Eur. J. 2000, 6, 2925.
41. Salahub, D. R.; Fournier, R.; Mlynarski, P.; Papai, I.; St-Amant, A.; Ushio, J. In Density Functional Methods In Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer: New York, 1991.
42. St.-Amant, A.; Salahub, D. R. Chem. Phys. Lett. 1990, 169, 387.
43. Malkin, V. G.; Malkina, O. L.; Casida, M. E.; Salahub, D. R. J. Am. Chem. Soc. 1994, 116, 5898.
44. Malkin, V. G.; Malkina, O. L.; Eriksson, L. A.; Salahub, D. R. In Modern Density Functional Theory: A Tool For Chemistry; Seminario, J. M., Politzer, P., Eds.; Elsevier: Amsterdam, 1995; Vol. 2.
45. Malkin, V. G.; Malkina, O. L.; Salahub, D. R. Chem. Phys. Lett. 1994, 221, 91.
46. Malkina, O. L.; Salahub, D. R.; Malkin, V. G. J. Chem. Phys. 1996, 105, 8793.
47. Perdew, J. P.; Wang, Y. Phys. Rev. B 1986, 33, 8800.
48. Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR Basic Principles and Progress; Springer: Berlin/Heidelberg. 1991; Vol. 213, p 165.
49. Comment on the notation used for the structures: the first numeral refers to the compound. 1-8, 9a/b, or 10a/b; the following in or out refers to the chair conformation of the heteroring; a subsequent a indicates an axial orientation of the N-substituent. otherwise it is equatorially oriented; and a final numeral or numeral and letter refers to the flap atom of the envelope conformation of the cyclopentane ring. By this manner each conformational structure is well, and uniquely, described.
50. Lazzeretti, P.; Malagoli, M.; Zanasi, R.; Della, E. W.; Lochert, I. J.; Giribet, C. G.; Ruiz de Azúa, M. C.; Contreras, R. H. J. Chem. Soc., Faraday Trans. 1995, 91, 4031.
51. Onak, T.; Jaballas, J.; Barfield, M. J. Am. Chem. Soc. 1999, 121, 2850.
52. Czernek, J.; Lang, J.; Sklenář, V. J. Phys. Chem. A 2000, 104, 2788.
53. Sychrovský, V.; Gräfenstein, J.; Cremer, D. J. Chem. Phys. 2000, 113, 3530.
54. Bucourt, R. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Wiley: New York, 1974; Vol. 8, p 186.
55. Tähtinen, P.; Sillanpää, R.; Stájer, G.; Szabó, A. E.; Pihlaja, K. J. Chem. Soc., Perkin Trans. 2 1999, 2011.
56. Roversi, E.; Scopelliti, R.; Solari, E.; Estoppey, R.; Vogel, P.; Braña, P.; Menéndez, B.; Sordo, J. A. Chem. Eur. J. 2002, 8, 1336.
57. Klinot, J.; Podlaha, J.; Podlahová, J.; Malý, K.; Petříček, V. Collect. Czech. Chem. Commun. 1989, 54, 725.