1H, 13C and 15N NMR study and molecular modelling of 2,3-di-substituted quinoxalines with sterically hindered aromatic and heteroaromatic substituents

Journal of Molecular Structure

Volumn 444, Issue 1-3, 1998, Pages 199-211

  Hilfert, L ^a   Sarodnick, G ^a   Kempter, G ^a   Kleinpeter, E ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

2,3 Disubstituted quinoxalines; Ab initio calculations; Conformational isomerism; NMR spectroscopy; Semi empirical calculations

Indexed keywords

EID: 0032536830     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(97)00381-5     Document Type: Article

References (34)

1. [1] K. Pihlaja, E. Kleinpeter: C-13 NMR Chemical Shifts in Structural and Stereochemical Analysis, VCH, New York, 1994.
2. [2] M. Begtrup, Acta Chem. Scand. 27 (1973) 3101.
3. [3] M. Begtrup, J. Elguero, R. Faure, P. Camps, C. Estopa, D. Ilavsky, A. Fruchier, C. Marzin, J. de Mendoza. Magn. Reson. Chem. 26 (1988) 134.
4. [4] M. Begtrup, Acta Chem. Scand. Sect. B 28 (1974) 61.
5. [5] C.W. Fong, Aust. J. Chem. 33 (1974) 1703.
6. [6] D. Leibfritz, Chem. Ber. 108 (1975) 3024.
7. [7] E. Kolehmainen, K. Laihia, R. Kauppinen, J. Phys. Org. Chem. 8 (1995) 577.
8. [8] M.A. Khadim, L.D. Colebrook, J. Magn. Reson. 23 (1985) 259.
9. [9] D.M. Grant, V.B. Cheney, J. Am. Chem. Soc. 89 (1967) 5315.
10. [10] C. Avendano, M. Espada, B. Ocana, S. Garcia-Granda, R. Diaz, B. Tejerina, F. Gómez-Beltrán, A. Martínez, J. Elguero, J. Chem. Soc., Perkin Trans. 2 (1993) 1547.
11. [11] P.J. Black, M.L. Heffernan, Aust. J. Chem. 18 (1965) 707.
12. [12] T.F. Page Jr., , T. Alger, D.M. Grant, J. Am. Chem. Soc. 87 (1965) 5333.
13. [13] M. Witanowski, L. Stefaniak, G.A. Webb, Org. Magn. Reson. 16 (1981) 309.
14. [14] L. Stefaniak, J.D. Roberts, M. Witanowski, G.A. Webb, Org. Magn. Reson. 22 (1984) 215.
15. [15] W.v. Philipsborn, R. Müller, Angew. Chem. 98 (1986) 331.
16. [16] H. Kessler, M. Gehrke, C. Griesinger, Angew. Chem 100 (1988) 507.
17. ® Molecular Modelling Software, Vision 6.1, TRIPOS, Inc., St.Louis/Missouri, USA (1994); J.J.P. Stewart, Frank J. Seiler, Research Laboratory, U.S. Air Force Academy, Colorado Springs, USA, QCPE No.455.
18. ® Molecular Modelling Software, Vision 6.1, TRIPOS, Inc., St.Louis/Missouri, USA (1994); J.J.P. Stewart, Frank J. Seiler, Research Laboratory, U.S. Air Force Academy, Colorado Springs, USA, QCPE No.455.
19. [18] Hehre, W.J., Radom, L., Schleyer, P.v.R., Pople, J.A., Ab-Initio Molecular Orbital Theory, Wiley and Sons, New York (1986); GAUSSIAN 94, Revision C.2, M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Ciosloski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
20. [18] Hehre, W.J., Radom, L., Schleyer, P.v.R., Pople, J.A., Ab-Initio Molecular Orbital Theory, Wiley and Sons, New York (1986); GAUSSIAN 94, Revision C.2, M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Ciosloski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
21. [19] J.B. Stothers, Carbon-13 NMR Spectroscopy. Academic Press, New York, 1972.
22. [20] S.P. Singh, D. Kumar, D. Kumar, A. Martinez, J. Elguero, J. Heterocycl. Chem. 33 (1996) 323.
23. [21] J.I. Kroschwitz, M. Winokur, H.J. Reich, J.D. Roberts, J. Am. Chem. Soc. 91 (1969) 5927.
24. [22] S.H. Grover, J.P. Guthrie, J.B. Stothers, C.T. Tan, J. Magn. Reson. 10 (1973) 227.
25. [23] R. Gallo, C. Roussel, U. Berg, Adv. Heterocycl. Chem. 43 (1988) 173.
26. [24] Y. Iwanami, T. Inagaki, J. Hetercycl. Chem. 13 (1976) 681.
27. [25] Y. Kurasawa, A. Ishikura, K. Ikeda, T. Hosaka, Y. Matsumoto, A. Takada, H.S. Kim, Y. Okamoto, J. Heterocycyl. Chem. 31 (1994) 233.
28. [26] R.A. More O'Ferrall, B.A. Murray. J. Chem. Soc. Perkin Trans. 2 (1994) 2461.
29. [27] A.R.E. Carey, R.A. More O'Ferrall, M.G. Murphy, B.A. Murray, J. Chem. Soc. Perkin Trans. 2 (1994) 2471.
30. [28] A.R. Katritzky, P. Barczynski, G. Musumarra, D. Pisano, M. Szafran, J. Am. Chem. Soc. 111 (1989) 7.
31. [29] G. Sarodnick, G. Kempter, A. Jumar, DD-Pat. 276479 (28.02.90); C.A. 114 (1991) 6543y.
32. [30] G. Sarodnick, G. Kempter, DD-Pat. 292001 (18.07.91); C.A. 115 (1991) 232294v.
33. [31] G. Sarodnick, G. Kempter, S. Kühne, DD-Pat. 276478 (28.02.90); C.A. 113 (1990) 231410b.
34. [32] G. Sarodnick, G. Kempter, A. Jumar, DD-Pat. 265896 (15.03.89); C.A. 111 (1989) 214507e.