Natural bond orbitals analysis of C-H ··· O interactions in NCH/H2O and NCH/OCH2, and their effect on nuclear magnetic shielding constants

Journal of Molecular Structure: THEOCHEM

Volumn 491, Issue 1-3, 1999, Pages 23-31

  Peralta, J E ^a   Ruiz De Azua M C ^a   Contreras, R H ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Bond orbitals; Oxygen atoms; Shielding constants

Indexed keywords

CARBON; HYDROGEN; OXYGEN; WATER;

ARTICLE; CHEMICAL BINDING; CHEMICAL INTERACTION; COMPLEX FORMATION; ENERGY; GEOMETRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY;

EID: 0033584882     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(99)00027-5     Document Type: Article

References (55)

1. R.D. Green, Hydrogen Bonding by C-H Groups, Macmillan, London, 1974.
2. A. Jeffrey, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991.
3. G.R. Desiraju, Acc. Chem. Res. 24 (1991) 290.
4. T. Steiner, J.v.d. Maas, B. Lutz, J. Chem. Soc. Perkin Trans. 2 (1997) 1287.
5. G. Felcy Fabiola, S. Krishnaswamy, V. Nagarajan, V. Pattabhi, Acta Cryst. D53 (1997) 316.
6. T. Steiner, E.B. Starikov, M. Tamm, J. Chem. Soc. Perkin Trans. 2 (1996) 67.
7. T. Steiner, J.A. Kanters, J. Kroon, J. Chem. Soc. Chem. Commun. (1996) 1277.
8. J.D. Chaney, C.R. Gross, K. Folting, B.D. Santarsiero, M.D. Hollingsworth, J. Am. Chem. Soc. 118 (1996) 9432.
9. L. Turi, J.J. Dannenberg, J. Phys. Chem. 99 (1995) 639.
10. F.P.S.C. Gil, J.J.C. Teixeira-dias, J. Mol. Struct. Theochem 363 (1996) 311.
11. T. Steiner, B. Lutz, J.v.d. Maas, N. Veldman, A.M.M. Schreurs, J. Kroon, J.A. Kanters, J. Chem. Soc. Chem. Commun. (1997) 191.
12. G. Müller, M. Lutz, S. Harder, Acta Cryst. B52 (1996) 1014.
13. B. Shulz, P. Botschwina, Chem. Phys. Lett. 243 (1995) 378.
14. B. Shulz, P. Botschwina, Mol. Phys. 89 (1996) 1553 (just to quote a few of the most recent papers) and references cited therein.
15. T. Steiner, Cryst. Rev. 6 (1996) 1.
16. T. Steiner, J. Chem. Soc. Chem. Commun. (1997) 727.
17. C. Vizioli, M.C. Ruiz de Azúa, C.G. Giribet, R.H. Contreras, L. Turi, J.J. Dannenberg, I.D. Rae, J.A. Weigold, M. Malagoli, R. Zanasi, P. Lazzeretti, J. Phys. Chem. 98 (1994) 8858.
18. C.G. Giribet, C.V. Vizioli, M.C. Ruiz de Azúa, R.H. Contreras, J.J. Dannenberg, A. Masunov, J. Chem. Soc. Faraday Trans. 92 (17) (1996) 3029.
19. A.V. Afonin, C. Vizidi, M.C. Ruiz de Azúa, R.H. Contreras, Bull. Acad. Sci. Russia, Div. Chem. Sci. 45 (6) (1996) 1362-1365.
20. A.V. Afonin, N.M. Peruchena, L. Sosa, R.H. Contreras, Russ. Chem. Bull. 46 (1997) 251.
21. G.L. Sosa, N.M. Peruchena, R.H. Contreras, E.A. Castro, J. Mol. Struct. Theochem 401 (1997) 77.
22. J. Cai, A.G. Davies, C.H. Schiesser, J. Chem. Soc. Perkin Trans. 2 (1994) 1151.
23. S.N. Vinograd, R.H. Linnell, Hydrogen bonding, Nostrand Reinhold (Van), New York, 1971, p. 47.
24. T. Steiner, J. Chem. Soc. Perkin Trans. 2 (1995) 1315.
25. I.D. Brown, Acta Cryst. B48 (1992) 553.
26. A.V. Afonin, M.A. Andriyankov, Zh. Org. Khim. 24 (1988) 1034.
27. A.V. Afonin, M.V. Sigalov, S.E. Korustova, I.A. Aliev, A.V. Vashchenko, B.A. Trofimov, Magn. Reson. Chem. 28 (1990) 580.
28. H. Satonaka, K. Abe, M. Hirota, Bull. Chem. Soc. Jpn. 61 (1988) 2031.
29. L. Turi, J.J. Dannenberg, J. Phys. Chem. 97 (1993) 7899.
30. R.F.W. Bader, Atoms in Molecules. A Quantum Theory, Clarendon, Oxford, 1990.
31. U. Koch, P.L.A. Popelier, J. Phys. Chem. 99 (1995) 9747.
32. I.C. Hayes, A.J. Stone, Mol. Phys. 53 (1984) 83.
33. B. Jeziorski, R. Moszynski, A. Ratkiewicz, S. Rybak, in: E. Clementi (Ed.), METECC94, B, STEF, Cagliari, 1993, p. 79.
34. A.E. Reed, L.A. Curtis, F.A. Weinhold, Chem. Rev. 88 (1988) 899.
35. F.A. Weinhold, J. Mol. Struct. Theochem 398/399 (1997) 181.
36. J.E. Del Bene, I. Shavitt, Molecular Interactions Ch. 5, in: S. Scheiner (Ed.), Wiley, New York, 1997.
37. K. Wolinski, J.F. Hinton, P. Pulay, J. Am. Chem. Soc. 112 (1990) 8251.
38. NBO version 3.1, E.D. Glendening, A.E. Reed, J.E. Carpenter, F. Weinhold.
39. A.D. Becke, J. Chem. Phys. 98 (1993) 5648.
40. A. Meunier, B. Levy, G. Berthier, Theoret. Chim. Acta 29 (1973) 49.
41. S.F. Boys, F. Bernardi, Mol. Phys. 19 (1970) 553.
42. I. Mayer, P.R. Surjan, Chem. Phys. Lett. 191 (1992) 497.
43. L. Turi, J.J. Dannenberg, J. Phys. Chem. 97 (1993) 2488.
44. GAUSSIAN 94, Revision D.4, 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. Cioslowski, 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, J.A. Pople, Gaussian Inc., Pittsburgh, PA, 1995.
45. M.J.S. Dewar, R.C. Dougherty, The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975.
46. T.A. Albright, J.K. Burdett, M.H. Whangbo, Orbital Interactions in Chemistry, Wiley, New York, 1985.
47. R.K. Harris, Nuclear Magnetic Resonance Spectroscopy, Pitman, London, 1983.
48. G. Jaccard, P.A. Carrupt, L. Lautervein, Magn. Reson. Chem. 26 (1988) 239.
49. T. Schaefer, J. Phys. Chem. 79 (1975) 1888.
50. P.E. Hansen, The Chemistry of Double-bonded Functional Groups Ch. 3, in: S. Patai (Ed.), Wiley, 1989 Ch.
51. B.L. Shapiro, R.M. Kopchic, S.J. Ebersole, J. Chem. Phys. 39 (1963) 3154.
52. A.L. Esteban, M.P. Galache, E. Díez, D.G. de Kowalewski, V.J. Kowalewski, J.E. Peralta, G. Eskuche, R.H. Contreras, Magn. Reson. Chem. (1999) in press.
53. P.E. Hansen, Prog. NMR Spectrosc. 14 (1981) 175.
54. A.S. Perlin, Pure App. Chem. 50 (1978) 1401.
55. 17O NMR Spectroscopy in Organic Chemistry Ch. 5, in: D.W. Boykin (Ed.), CRC Press, Boca Raton, 1991.