Structural Chemistry

, Volume 9, Issue 3, pp 187–202 | Cite as

Ab Initio (GIAO) Calculations of Absolute Nuclear Shieldings for Representative Compounds Containing 1(2)H, 6(7)Li, 11B, 13C, 14(15)N, 17O, 19F, 29Si, 31P, 33S, and 35Cl Nuclei

Abstract

Two kinds of ab initio calculations (B3LYP and HF) using the GIAO approach have been carried out for fifteen H, three Li, three B, eleven C, seven N, nine O, four F, three Si, four P, six S and five Cl containing derivatives. The calculated absolute nuclear shieldings have been compared with experimental absolute values (either measured or estimated from relative chemical shifts) when available or with relative chemical shifts (11B, 35Cl). The correlations range from good to excellent and only three compounds (PN, P2H2, SO2) deviate significantly.

GIAO DFT HF/6-311 + +G** absolute nuclear shieldings 

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REFERENCES

  1. 1.
    Ditchfield, R. Mol. Phys. 1974, 27, 789. Chesnut, D. B. Ab initio calculations of NMR chemical shielding, in Annu. Rep. NMR Spectrosc. 1994, 29, 1. Iuliucci, R. J.; Facelli, J. C.; Alderman, D. W.; Grant, D. M. J. Am. Chem. Soc. 1995, 117, 2336. Pulay, P.; Hinton, J. F. Encyclopedia of Nuclear Magnetic Resonance, vol. 7; Wiley: New York, p. 4337.Google Scholar
  2. 2.
    Becke, A. D. J. Chem. Phys. 1993, 98, 5648.CrossRefGoogle Scholar
  3. 3.
    Hehre, W. J.; Radom, L.; Schleyer, P. von R.; Pople, J. A. Ab Initio Molecular Theory; Wiley: New York, 1986. Krishnam, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1984, 80, 3265.Google Scholar
  4. 4.
    Kutzelnigg, W.; Wüllen, Ch. V.; Fleischer, U.; Franke, R.; Mourik, T. V. Nuclear Magnetic Shieldings and Molecular Structure; Tossell, J. A., ed.; Kluwer Academic Publishers: Dordrecht, 1993.Google Scholar
  5. 5.
    Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortíz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andrés, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; González, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.Google Scholar
  6. 6.
    Chesnut, D. B.; Wright, D. W. J. Comput. Chem. 1991, 12, 546.Google Scholar
  7. 7.
    Schreckenbach, G.; Ziegler, T. J. Phys. Chem. 1995, 99, 606.Google Scholar
  8. 8.
    Rauhut, G.; Puyear, S.; Wolinski, K.; Pulay, P. J. Phys. Chem. 1996, 100, 6310.Google Scholar
  9. 9.
    Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497.Google Scholar
  10. 10.
    Chesnut, D. B. Chem. Phys. 1997, 214, 73.Google Scholar
  11. 11.
    Jameson, C. J. Theoretical and physical aspects of nuclear shielding, Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1994, 23, 47.Google Scholar
  12. 12.
    Jameson, C. J. Understanding NMR chemical shifts, Annu. Rev. Phys. Chem. 1996, 47, 135. See also Günther, H. Encyclopedia of Nuclear Magnetic Resonance, vol. 5; Wiley: New York, 1996, p. 2807.Google Scholar
  13. 13.
    Liu, F.; Phung, C. G.; Alderman, D. W.; Grant, D. M. J. Am. Chem. Soc. 1996, 118, 10629. See also Reed, D. Encyclopedia of Nuclear Magnetic Resonance, vol. 2; Wiley: New York, 1996, p. 1002.Google Scholar
  14. 14.
    Barszczewicz, A.; Janzunski, M.; Jackowski, K. Chem. Phys. Lett. 1993, 203, 404.Google Scholar
  15. 15.
    Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Tabellen zur Strukturaufklärung Organischer Verbindungen mit Spektroskopischen Methoden; Springer-Verlag: Berlin, 1976.Google Scholar
  16. 16.
    Nöth, H.; Vahrenkamp, H. J. Organomet. Chem. 1968, 12, 23, 281.Google Scholar
  17. 17.
    Pople, J. A.; Schneider, W. G.; Bernstein, H. J. Highresolution Nuclear Magnetic Resonance; McGraw-Hill: New York, 1959.Google Scholar
  18. 18.
    Jackman, L. M.; Sternhell, S. Applications of NMR Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon Press: Oxford, 1969.Google Scholar
  19. 19.
    Emsley, J. W.; Feeney, J.; Sutcliffe, L. H. High Resolution NMR Spectroscopy, vol. 2; Pergamon Press: Oxford, 1966, p. 667.Google Scholar
  20. 20.
    Fritz, H.; Kristinsson, H.; Mollenkopf, M.; Winkler, T. Magn. Reson. Chem. 1990, 28, 331.Google Scholar
  21. 21.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1983, 12, 1.Google Scholar
  22. 22.
    Seitz, L. M.; Brown, T. L. J. Am. Chem. Soc. 1966, 88, 2174.Google Scholar
  23. 23.
    Scherr, P. A.; Hogan, R. J.; Oliver, J. P. J. Am. Chem. Soc. 1974, 96, 6055.Google Scholar
  24. 24.
    Wrackmeyer, B. Annu. Rep. NMR Spectrosc. 1988, 20, 61.Google Scholar
  25. 25.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1995, 24, 44.Google Scholar
  26. 26.
    Jameson, A. K.; Jameson, C. J. Chem. Phys. Lett. 1987, 134, 461.Google Scholar
  27. 27.
    Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley and Sons: Chichester, 1984.Google Scholar
  28. 28.
    Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic Press: New York, 1972.Google Scholar
  29. 29.
    Olsson, L.; Cremer, D. J. Phys. Chem. 1996, 100, 16881.Google Scholar
  30. 30.
    Gauss, J.; Stanton, J. F. J. Chem. Phys. 1995, 103, 3561.Google Scholar
  31. 31.
    Schreckenbach, G.; Ziegler, T. J. Phys. Chem. 1995, 99, 606.Google Scholar
  32. 32.
    Somayajulu, G. R.; Kennedy, J. R.; Vickrey, T.; Zwolinski, B. J. J. Magn. Reson. 1979, 33, 559.Google Scholar
  33. 33.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1996, 25, 39.Google Scholar
  34. 34.
    Witanowski, M.; Stefaniak, L.; Webb, G. A. Annu. Rep. NMR Spectrosc. 1986, 18, 68.Google Scholar
  35. 35.
    Witanowski, M.; Stefaniak, L.; Szymanski, S.; Januszewski, H. J. Magn. Reson. 1977, 28, 217.Google Scholar
  36. 36.
    Claramunt, R. M.; Sanz, D.; López, C.; Jiménez, J. A.; Jimeno, M. L.; Elguero, J.; Fruchier, A. Magn. Reson. Chem. 1997, 35, 35.Google Scholar
  37. 37.
    Hayashi, S.; Hayamizu, K. Bull. Chem. Soc. Jpn. 1991, 64, 688.Google Scholar
  38. 38.
    Chesnut, D. B. Annu. Rep. NMR Spectrosc. 1994, 29, 71.Google Scholar
  39. 39.
    Malkin, V. G.; Malkina, O. L.; Salahub, D. R. Chem. Phys. Lett. 1993, 204, 87.Google Scholar
  40. 40.
    Kintzinger, J.-P. Oxygen NMR. Characteristic parameters and applications, in NMR Basic Principles and Progress, vol. 17, P. Diehl, E. Fleck, and R. Kosfeld, eds.; Springer-Verlag: Berlin, 1981, p. 1.Google Scholar
  41. 41.
    Cavalli, Ł. Annu. Rep. NMR Spectrosc. 1976, 6B, 43.Google Scholar
  42. 42.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1989, 18, 1.Google Scholar
  43. 43.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1990, 19, 1.Google Scholar
  44. 44.
    Mallion, R. B. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1975, 4, 1.Google Scholar
  45. 45.
    Williams, E. A. Annu. Rep. NMR Spectrosc. 1983, 15, 235.Google Scholar
  46. 46.
    Raynes, W. T. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1973, 2, 1.Google Scholar
  47. 47.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1991, 20, 48.Google Scholar
  48. 48.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1992, 21, 36.Google Scholar
  49. 49.
    Jameson, C. J. Nucl. Magn. Reson. Specialist Periodical Reports Chem. Soc. 1986, 15, 1.Google Scholar
  50. 50.
    Hinton, J. F. Annu. Rep. NMR Spectrosc. 1987, 19, 1.Google Scholar
  51. 51.
    Faure, R.; Vincent, E.-J.; Ruiz, J. M.; Léna, L. Org. Magn. Reson. 1981, 15, 401.Google Scholar
  52. 52.
    Lindman, B.; Forsén, S. Chlorine, bromine and iodine NMR. Physico-chemical and biological applications, in NMR Basic Principles and Progress, vol. 12, P. Diehl, E. Fluck, and R. Kosfeld, eds.; Springer-Verlag: Berlin, 1976, p. 1.Google Scholar
  53. 53.
    Fowler, P. W.; Legon, A. C.; Peebles, S. A.; Steiner, E. Chem. Phys. Lett. 1995, 238, 163.Google Scholar
  54. 54.
    Legon, A. C. Personal communication.Google Scholar
  55. 55.
    Lambert, J. B.; Wharry, S. M.; Block, E.; Bazzi, A. A. J. Org. Chem. 1983, 48, 3982.Google Scholar
  56. 56.
    Ruostesuo, P.; Pirilä-Honkanen, P.; Heikkinen, L. J. Phys. Org. Chem. 1989, 2, 565.Google Scholar
  57. 57.
    Chesnut, D. B. The ab initio computation of nuclear magnetic resonance chemical shielding, in Reviews of Computational Chemistry, vol. 8, K. B. Lipkowitz and D. B. Boyd, eds.; VCH Publishers: New York, 1996, pp. 245–297.Google Scholar
  58. 58.
    Suárez, C.; True, N. S.; Weiss, B. E. Bol. Soc. Chil. Quím. 1989, 34, 15 (Chem. Abstr. 1989, 111, 193987u).Google Scholar
  59. 59.
    Wasylishen, R. E.; Mooibroaek, S.; Macdonald, J. B. J. Chem. Phys. 1984, 81, 1057.Google Scholar
  60. 60.
    Jameson, C. J.; Jameson, A. K.; Burrell, P. M. J. Chem. Phys. 1980, 73, 6013.Google Scholar
  61. 61.
    Jameson, C. J.; Jameson, A. K.; Honarbakhsh, J. J. Chem. Phys. 1984, 81, 5266.Google Scholar
  62. 62.
    Jameson, C. J.; De Dios, A. C.; Jameson, A. K. Chem. Phys. Lett. 1990, 167, 575.Google Scholar
  63. 63.
    Wasylishen, R. E.; Connor, C.; Friedrich, J. O. Can. J. Chem. 1984, 62, 981.Google Scholar
  64. 64.
    Jameson, C. J.; Jameson, A. K.; Oppusunggu, D.; Wille, S.; Burrell, P. M.; Mason, J. J. Chem. Phys. 1981, 74, 81.Google Scholar
  65. 65.
    De Dias, A. C.; Jameson, C. J. Annu. Rep. NMR Spectrosc. 1994, 29, 1.Google Scholar
  66. 66.
    Alei, M.; Florin, A. E.; Litchman, W. M.; O'Brien, J. F. J. Phys. Chem. 1971, 75, 932.Google Scholar

Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  1. 1.Instituto de Química MédicaCSICMadridSpain

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