NMR J(13C,13C) spin-spin coupling constants in pyridine-carboxaldehydes. Experimental and DFT-B3LYP studies

Journal of Molecular Structure

Volumn 754, Issue 1-3, 2005, Pages 1-9

  Taurian, Oscar E ^a,b   De Kowalewski, Dora G ^c   Pérez, Jorge E ^a   Contreras, Rubén H ^c  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

^b UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Conjugative interactions; Geminal couplings; Negative hyperconjugative interactions; Scalar couplings; Stereospecificity

Indexed keywords

ALDEHYDES; CARBON MONOXIDE; CONFORMATIONS; CONTINUUM MECHANICS;

ANTIBONDING ORBITALS; CONJUGATIVE INTERACTIONS; PYRIDINE ALDEHYDES;

MOLECULAR STRUCTURE;

EID: 27544476516     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2005.06.002     Document Type: Article

References (53)

1. V. Sychrovský, J. Gräfenstein, and D. Cremer J. Chem. Phys. 113 2000 3530
2. T. Helgaker, M. Watson, and N.C. Handy J. Chem. Phys. 113 2000 9402
3. V. Barone, J.E. Peralta, R.H. Contreras, and J.P. Snyder J. Phys. Chem., A 106 2002 5607
4. J.E. Peralta, V. Barone, G.E. Scuseria, and R.H. Contreras J. Am. Chem. Soc. 126 2004 7428
5. J.L. Marshall A.P. Marchand Methods in Stereochemical Analysis vol. 2 1983 Verlag Chemie Deerfield Beach, FL
6. L.B. Krivdin, and G.A. Kalabin Prog. NMR Spectrosc. 21 1989 293
7. L.B. Krivdin, and E.W. Della Prog. NMR Spectrosc. 23 1991 301
8. K. Kamienska-Trela Ann. Rep. NMR Spectrosc. 30 1995 131
9. L.B. Krivdin, and S.V. Zinchenko Curr. Org. Chem 2 1998 173
10. G.J. Karabastos, and F.M. Vane J. Am. Chem. Soc. 85 1963 3886
11. R. Wasylishen, and T. Schaefer Can. J. Chem. 49 1971 3216
12. I.J.P. Dorie, M.L. Martín, S. Barnier, M. Blain, and S. Odiot Org. Magn. Reson. 3 1971 661
13. M.R. Bramwell, and E.W. Randall Spectrochim. Acta, A 26 1970 1877
14. W. Danchura, T. Schaefer, J.B. Rowbotham, and D.J. Wood Can. J. Chem. 52 1974 3986
15. R.J.W. LeFevre, and P.J. Stiles J. Chem. Soc. B 1966 420
16. P.E. Hansen S. Patai The Chemistry of Double-bonded Functional Groups 1989 Wiley New York Chapter 3
17. D.G. de Kowalewski, E. Díez, A.L. Esteban, V. Barone, J.E. Peralta, and R.H. Contreras Magn. Reson. Chem. 42 2004 938
18. D.G. de Kowalewski, R.H. Contreras, E. Díez, and A.L. Esteban Mol. Phys. 102 2004 2607
19. A. Bax, R. Freeman, and T.A. Frenkiel J. Am. Chem. Soc. 103 1981 2102
20. A.D. Becke J. Chem. Phys. 98 1993 5648
21. P. Lantto, J. Vaara, and T. Helgaker J. Chem. Phys. 117 2002 1
22. S.N. Maximoff, J.E. Peralta, V. Barone, G.E. Scuseria., J. Chem. Theory Comput.,. in press
23. V. Barone J. Chem. Phys. 101 1994 6834
24. J.E. Peralta, G.E. Scuseria, J.R. Cheeseman, and M.J. Frisch Chem. Phys. Lett. 375 2003 452
25. M. Cossi, V. Barone, B. Mennuci, and J. Tomasi Chem. Phys. Lett. 286 1998 253
26. B. Mennucci, and J. Tomasi J. Chem. Phys. 106 1997 5151
27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, 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, C. Gonzalez, J.A. Pople, gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh PA, 2003.
28. A.E. Reed, L.A. Curtis, and F. Weinhold Chem. Rev. 88 1988 899
29. E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold, Included in the Gaussian 03 package of programs, NBO version 3.1.
30. A.J. Kirby The Anomeric Effect and Related Stereoelectronic Effects at Oxygen 1983 Springer Berlin pp. 1-150
31. A.E. Reed, and P.v.R. Schleyer J. Am. Chem. Soc. 112 1990 1434
32. E.L. Eliel, and G.A. Giza J. Org. Chem. 33 1968 3754
33. R.U. Lemeiux, A.A. Pavia, J.C. Marti, and K.A. Watanabe Can. J. Chem. 47 1969 4427
34. D.G. Zaccari, J.P. Snyder, J.E. Peralta, O.E. Taurian, R.H. Contreras, and V. Barone Mol. Phys. 100 2002 705
35. D. Zaccari, V. Barone, J.E. Peralta, R.H. Contreras, O.E. Taurian, E. Díez, and A.E. Esteban Int.J. Mol. Sci. 4 2003 93
36. R.H. Contreras, and E. Peralta Prog. NMR Spectrosc. 37 2000 321
37. R.H. Contreras, V. Barone, J.E. Peralta, and J.C. Facelli Ann. Rep. NMR Spectrosc. 51 2003 167
38. M.A. Watson, P. Salek, P. Macak, M. Jaszunski, and T. Helgaker Chem. Eur. J. 10 2004 4627
39. R.H. Contreras, J.E. Peralta, V. Barone, G.E. Scuseria, Adv. Quantum Chem. 48 (2005) 127.
40. W.S. Lee, and J.M. Schulman J. Chem. Phys. 70 1979 1530
41. J.E. Pérez, F.S. Ortiz, R.H. Contreras, C.G. Giribet, and M.C. Ruiz de Azúa J. Mol. Struct. (Theochem) 210 1990 193
42. H. Seel, and H. Günther J. Am. Chem. Soc. 102 1980 7051
43. V.M.S. Gil, and W.v. Philipsborn Magn. Reson. Chem. 27 1989 409
44. R.H. Contreras, J.E. Peralta, C.G. Giribet, M.C. Ruiz de Azúa, and J.C. Facelli Ann. Rep. NMR Spectrosc. 41 2000 55
45. C.F. Tormena, R. Rittner, R.H. Contreras, and J.E. Peralta J. Phys. Chem. A 108 2004 7762
46. R.H. Contreras, M.A. Natiello, M.F. Tufró, and G. de Kowalewski Z. Physik. Chem. 267 1986 289
47. M. Barfield, and B. Chakrabarti Chem. Rev. 69 1969 757
48. A.R. Engelman, G.E. Scuseria, and H. Contreras J. Magn. Reson. 50 1982 21
49. T.W. Keal, D.J. Tozer, and T. Helgaker Chem. Phys. Lett. 391 2004 374
50. O.B. Lutnæs, T.A. Ruden, and T. Helgaker Magn. Reson. Chem. 42 2004 S117
51. R.D. Wigglesworth, W.T. Raynes, S. Kirpekar, J. Oddershede, and P.A. Sauer J. Chem. Phys. 112 2000 3735
52. T.A. Ruden, O.B. Lutnæs, T. Helgaker, and K. Ruud J. Chem. Phys. 118 2003 9572
53. D.G. de Kowalewski, V.J. Kowalewski, J.E. Peralta, G. Eskuche, R.H. Contreras, A.L. Esteban, and M.P. Galache E. Díez, Magn. Reson. Chem. 37 1999 227