13C NMR chemical shift calculations for some substituted pyridines: A comparative consideration

Journal of Chemical Information and Computer Sciences

Volumn 37, Issue 4, 1997, Pages 726-730

  Thomas, St ^a   Bruhl I ^a   Heilmann, D ^a   Kleinpeter, E ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000282350     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci970440i     Document Type: Review

References (55)

1. 13C NMR spectra of aromatic compounds. J. Chem. Inf. Comput. Sci. 1994, 34, 725-729.
2. 13C-chemischen Verschiebungen Monatsh. Chem. 1992, 123, 769.
3. Fürst, A.; Pretsen, E. A Computer Program for the prediction of C-13 NMR chemical shifts of organic compounds. Anal. Chim. Acta 1990, 229, 17-25.
4. 3-hybridized carbon atoms in organic compounds. Anal. Chim. Acta 1990, 233, 213-222.
5. 2- and sp-hybridized carbon atoms in organic compounds. Anal. Chim. Acta 1991, 248, 415-428.
6. 13C NMR spectra based on an open set of additivity rules. J. Chem. Inf. Comput. Sci. 1992, 32, 291-295.
7. Barth, A. Specinfo - An integrated spectroscopic information system. J. Chem. Inf. Comput. Sci. 1993, 33, 52-58.
8. 13C NMR spectral simulation and shift prediction. Trends Anal. Chem. 1994, 13, 95-104.
9. Cheng, H. N.; Kasehagen, L. J. Integrated approach for C nuclear magnetic resonance shift prediciton, spectral simulation and library search. Anal. Chim. Acta 1994, 285, 223-235.
10. gNMR, Version 3.6-DEMO by Cherwell Scientific Publishing (http: //www.cherwell.com). Publications are in preparation (private communication from Cherwell).
11. CNMR Version2.0-Demo from Adv. Chem. Developm., Inc (http:// www.acdlabs.com).
12. HyperNMR by Hypercube (http://www.hyper.com), evaluation copy by courtesy of science direct (http://www.sciencedirect.com).
13. 13C NMR chemical shifts. Magn. Reson. Chem. 1992, 30, 240-248.
14. Robien, W. Computer-assisted assignment of C-13 NMR spectra. Monaish. Chem. 1983, 114, 365.
15. Kalchhauser, H.; Robien, W. Csearch - A computer program for identification of organic compounds and fully automated assignment of C-13 NMR spectra. J. Chem. Inf. Comput. Sci. 1985, 25, 103-106.
16. Bax, A. Structure determination and spectral assignment by pulsed polarisation transfer via long-range proton-carbon-13 couplings. J. Magn. Reson. 1984, 57, 314-318.
17. Bax, A.; Summers, M. F. Proton and carbon-13 assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 1986, 108, 2093-2094.
18. 1 (COLOC). J. Magn. Reson. 1984, 57, 331-336.
19. 13C substitutent effects in monosubstituted benzenes. Org. Magn. Reson. 1979, 12, 499-524.
20. Bremser, W.; Franke, B.; Wagner, H. Chemical shift ranges in 13-C NMR-spectroscopy; VCH Verlag: Weinheim, 1986.
21. 13C NMR Spektren Cl- substituierter 4-Nitro-N,N-dimethylaniline. J. Prakt. Chem. 1985, 327, 161-165.
22. Ströhl, D.; Radeglia, R.; Brunn, J.; Fanghänel, E. 1,3,4,5-Tetrasubstituierte Benzene. J. Prakt. Chem. 1989, 331, 361.
23. Nyquist, R. A.; Haska, D. L. Correlation of infrared and NMR data for some substituted benzenes. Appl. Spectrosc. 1991, 45, 849.
24. 13C-NMR Spektroskopie; G. Thieme-Verlag: Stuttgart-New York, 1984.
25. Chem Window is a registred trademark of SoftShell International, Ltd.; for more information: http://www.softshell.com/.
26. Wolinski, K.; Hinton, J. F.; Pulay, P. Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical-Shift Calculations. J. Am. Chem. Soc. 1990, 112, 8251-8260.
27. Wishart, D. S.; Sykes, B. D.; Richards, F. M. The Chemical-Shift Index-aA fast and simple method for the assignment of protein secondary structure though NMR spectroscopy. Biochemistry 1992, 31, 1647-1651.
28. Pastore, A.; Saudek, V. The relationship between chemical shift and secondary structure in proteins. J. Magn. Reson. 1990, 90, 165-176.
29. Ellis, P. D.; Maciel, G. E.; McIver, J. W., Jr. INDO [intermediate neglect of differential overlap] perturbation theory of magnetic shielding constants. Carbon-13 chemical shifts. J. Am. Chem. Soc. 1972, 94, 4069-4076.
30. Blizzard, A. C.; Santry, D. P. Self-consistent perturbation theory of nuclear spin-coupling constants. Application to couplings involving carbone and fluorine. J. Phys. Chem. 1971, 55, 950-963.
31. Pople, J. A.; McIver, J. W., Jr.; Ostlund, N. S. Self-consistent perturbation theory. I. Finite perturbation methods. J. Chem. Phys. 1968, 49, 2960-2964.
32. Pople, J. A.; McIver, J. W., Jr.; Ostlund, N. S. Self-consistent perturbation theory. II. Nuclear-spin coupling constants. J. Chem. Phys. 1968, 49, 2965-2970.
33. Maciel, G. E.; McIver, J. W., Jr.; Ostlund, N. S.; Pople, J. A. Approximate self-consistent molecular orbital theory of nuclear spin coupling. II. Fermi contact contributions to coupling between carbon and directly bonded atoms. J. Am. Chem. Soc. 1970, 92, 11-18.
34. Ducasse, L.; Hoarau, J.; Pesquer, M. Extended Hueckel calculation of protein chemical shifts with the aid of gauge invariant atomic orbitals. Application to hydrocarbons. Mol. Phys. 1980, 40, 1249-1259.
35. Kondo, M.; Ando, L.; Chujo, R.; Nishioka, A. Theoretical calculation of carbon-13 NMR shielding constants and their tensors in hydrocarbons by the finite perturbation method. J. Magn. Reson. 1976, 24, 315-326.
36. Vauthier, E. C.; Odiot, S.; Tonnard, F. Calculation of chemical shifts on INDO level with GIAO and London aproximation using finite perturbation method. I. Carbon-13 and proton. Can. J. Chem. 1982, 60, 957-969.
37. Vauthier, E. C.; Fliszar, S.; Tonnard, F.; Odiot, S. Nuclear magnetic shielding calculation in the finite perturbation method involving GIAO's at the INDO level and london's approximation. II. Carbon-13 and nitrogen-15. Can. J. Chem. 1983, 61, 1417-1421.
38. Baker, J. D.; Zerner, M. C. Calculation of C-13 NMR chemical shift using the intermediate neglect of differential-overlap model. Int. J. Quantum Chem. 1992, 43, 327-342.
39. Pople, J. A.; Beveridge, D. V. Approximate Molecular Orbital Theory; McGraw-Hill: New York, 1970.
40. Anderson, W. P.; Cundari, T. R.; Zerner, M. C. An intermediate neglect of differential-overlap model for 2nd-row transition metal species. Int. J. Quantum. Chem. 1991, 39, 31-45.
41. Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. Ground states of molecules XXVI. MINDO/3 calculations for hydrocarbons. J. Am. Chem. Soc. 1975, 97, 1294-1301.
42. Li, J.; Demello, P. C.; Jug, K. Extension of Sindol to transition metal compounds. J. Comput. Chem. 1992, 13, 85-92.
43. Dewar, M. J. S.; Thiel, W. Ground states of molecules. 38. The MNDO method. Approximations and parameters. J. Am. Chem. Soc. 1977, 99, 4899-4907.
44. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
45. Stewart, J. J. P. Optimization of parameters for semiempirical methods. 2. Applications. J. Comput. Chem. 1989, 10, 221-264.
46. Fraser, M.; Hayes, D. M. Quantum Chemistry Program Exchange, QCPE Program No. 389, Indiana University.
47. Fukui, H. Magn. Reson. Rev. 1987, 11, 205.
48. Anderson, W. A. Nucleare magnetic resonance spectra of some hydrocarbons. Phys. Rev. 1956, 102, 151-167.
49. Johnson, F.; LeRoy; Jankowsky, W. C. Carbon-13 NMR Spectra; John Wiley & Sons: New York, London, Sydney, Toronto, 1972.
50. 13C Contact Shifts of σ-bonded Molecules. J. Chem. Soc., Perkin Trans. 2 1977, 809-814.
51. Cook, I. B.; Caveat, S. Regarding the use of substituent parameters in statistical analyses of molecular properties. II - case study: Carbon-13 NMR of 2-substituted pyridines and monosubstituted benzenes. Aust. J. Chem. 1989, 42, 1493-1518.
52. 1H coupling constants. IV - Methoxy-, amino- and hydroxy-pyridines Org. Magn. Reson. 1975, 7, 244-246.
53. Iddon, B.; Mack, A. G.; Suschitzky, H.; Taylor, A. J.; Wakefield, B. J. Polyhalogeno-aromatic compounds. Part 42. 13 C NMR spectra of polyhalogeno-pyridines and -pyrimidines. J. Chem. Soc., Perkin Trans. 1 1980, 1370-1380.
54. 13C NMR shift prediction program for polysubstituted benzenes and sterically defined cyclohexane derivatives. Magn. Reson. Chem. 1996, 34, 395-415.
55. Demonstration of a new calculation and database program from Bruker at the northern german nmr meeting (March 3, 1997).