The effect of electron-withdrawing groups on 15N and 13C chemical shifts: A density functional study on a series of pyrroles

Molecular Physics

Volumn 103, Issue 6-8, 2005, Pages 1113-1129

  Mothana, B ^a   Ban, F ^a   Boyd, R J ^a   Thompson, A ^a   Hadden, C E ^b  

^a DALHOUSIE UNIVERSITY   (Canada)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ELECTRONIC STRUCTURE; PARAMAGNETISM; PROBABILITY DENSITY FUNCTION;

ELECTRON-WITHDRAWING GROUPS (EWG); PYRROLES;

NITROGEN;

EID: 27944469990     PISSN: 00268976     EISSN: 13623028     Source Type: Journal    
DOI: 10.1080/00268970412331333519     Document Type: Article

References (35)

1. A. Thompson, S. Gao, G. Modzelewska, D.S. Hughes, B. Patrick, D. Dolphin, Org. Lett., 2, 3587 (2000).
2. A.D. Abell, B.K. Nabbs, A.R. Battersby, J. Am. Chem. Soc., 120, 1741 (1998).
3. S. Singh, G.P. Basmadjian, Tetrahedron Lett., 38, 6829 (1997).
4. D.F. Huang, T.Y. Shen, Tetrahedron Lett., 34, 4477-4480 (1993).
5. H.M.L. Davies, E. Saikali, W.B. Young, J. Org. Chem., 56, 5696 (1991).
6. S.R. Tanny, J. Grossman, F.W. Fowler, J. Am. Chem. Soc., 94, 6495 (1972).
7. T.J. Donohoe, P.M. Guyo, J. Org. Chem., 61, 7664 (1996).
8. M. Gharpure, A. Stoller, F. Bellamy, G. Firnau, V. Snieckus, Synthesis, 1079 (1991).
9. D. Xiao, J.A. Schreier, J.H. Cook, P.G. Seybold, D.M. Ketcha, Tetrahedron Lett., 37, 1523 (1996).
10. V.H. Rawal, R.J. Jones, M.P. Cava, J. Org. Chem., 52, 19 (1987).
11. J. Wang, A.I. Scott, Tetrahedron Lett., 37, 3247 (1996).
12. L.F. Tietze, G. Kettschau, K. Heitmann, Synthesis, (7), 851 (1996).
13. A.D. Miller, F.J. Leeper, A.R. Battersby, J. Chem. Soc., Perkin Trans. 1, (11), 1943 (1989).
14. C. Hansch, A. Leo, R.W. Taft, Chem. Rev., 91, 165 (1991).
15. A.C. de Dios, E. Oldfield, Solid State Nucl. Magn. Reson., 6, 101 (1996).
16. T. Helgaker, M. Jaszunski, K. Ruud, Chem. Rev., 99, 293 (1999).
17. N.F. Ramsey, Phys. Rev., 78, 699 (1950).
18. P.J. Hore, Nuclear Magnetic Resonance, Oxford University Press, Oxford (1995).
19. J.A. Pople, Disc. Far. Soc., 34, 7 (1962).
20. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, 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, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, 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, 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.11.2, Gaussian, Inc. (2001).
21. B. Mothana, F. Ban, R.J. Boyd, Chem. Phys. Lett., 401, (2004).
22. J.D. Walsh, A. Miller, J. Phys. Chem. B, 107, 854 (2003).
23. R.J. Boyd, S.L. Boyd, J. Am. Chem. Soc., 114, 1652 (1992).
24. J.A. Bohmann, F. Weinhold, T.C. Farrar, J. Chem. Phys., 107, 1173 (1997).
25. E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, J.A. Bohmann, C.M. Morales, F. Weinhold, NBO 5.0, Theoretical Chemistry Institute, University of Wisconsin (2001).
26. J.B.Paine III, D. Dolphin, J. Org. Chem., 50, 5598 (1985).
27. J.A. Ganske, R.K. Pandey, M.J. Postich, K.M. Snow, K.M. Smith, J. Org. Chem., 54, 4801 (1989).
28. M.W. Moon, L.T. Bell, D.M. Webster, J. Org. Chem., 39, 315 (1974).
29. P.J. Wilson, R.D. Amos, N.C. Handy, Mol. Phys., 97, 757 (1999).
30. G.A. Webb, In Encyclopedia of Nuclear Magnetic Resonance, D.M. Grant, R.K. Harris (Eds), pp. 4307-4318, John Wiley, New York (1996).
31. P. Pulay, J.F. Hinton, In Encyclopedia of Nuclear Magnetic Resonance, D.M. Grant, R.K. Harris (Eds), pp. 4334-4339, John Wiley, New York (1996).
32. B. Mennucci, J.M. Martinez, J. Tomasi, J. Phys. Chem. A, 105, 7287 (2001).
33. M.S. Solum, J.C. Facelli, J. Michl, D.M. Grant, J. Am. Chem. Soc., 108, 6464 (1986).
34. M.S. Solum, K.L. Altman, M. Strohmeier, D.A. Berges, Y. Zhang, J.C. Facelli, R.J. Pugmire, D.M. Grant, J. Am. Chem. Soc., 119, 9804 (1997).
35. T. Gregor, F. Mauri, R. Car, J. Chem. Phys., 111, 1815 (1999).