A graphical tool for the prediction of vicinal proton-proton 3JHH coupling constants

Journal of Chemical Information and Computer Sciences

Volumn 44, Issue 5, 2004, Pages 1680-1685

  Navarro Vázquez, Armando ^a   Carlos, Juan Carlos ^a   Sardina, Francisco Javier ^a   Casanueva, Jorge ^b   Díez, Ernesto ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DATA REDUCTION; ETHANE; HYDROCARBONS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

COUPLING CONSTANT; ELECTRONEGATIVITY; SUBSTITUENT EFFECTS; VALENCE BONDS;

PROTONS;

EID: 5444262691     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci049913t     Document Type: Article

References (23)

1. (a) Karplus, M. Contact Electro-Spin Coupling of Nuclear Magnetic Moments. J. Chem. Phys. 1959, 30, 11-15.
2. (b) Karplus, M. Vicinal Proton Coupling in Nuclear Magnetic Resonance. J. Am. Chem. Soc. 1963, 85, 2870-2871.
3. Altona, C. Vicinal Coupling Constants & Conformation of Biomolecules. Encyclopedia of NMR; Grant, D. M., Morris, R., Eds.; Wiley: New York, 1996; pp 4909-4923.
4. Haasnoot, C. A. O.; De Leeuw, F. A. A. M.; Altona, C. The Relationship Between Proton-Proton NMR Coupling Constants and Substituent Electronegativities-I. An Empirical Generalization of the Karplus Equation. Tetrahedron 1980, 36, 2783-2792.
5. Balacco, G. A Desktop Calculator for the Karplus Equation. J. Chem. Inf. Comput. Sci. 1996, 36, 885-887.
6. 1H NMR Data. Tetrahedron Comput. Method. 1990, 3, 113-118. (c) Padrta, P.; Sklenár, V. Program Mulder - A tool for extracting torsion angles from NMR data. J. Biomol. NMR. 2002, 24, 339-349. (d) Neidig, K.-P.; Geyer, M.; Goerler, A.; Antz, C.; Saffrich, R.; Beneicke, W.; Kalbitzer, H. R. Aurelia, a program for computer aided analysis of multidimensional NMR spectra. J. Biomol. NMR. 1995, 6, 255-270.
7. 1H NMR Data. Tetrahedron Comput. Method. 1990, 3, 113-118. (c) Padrta, P.; Sklenár, V. Program Mulder - A tool for extracting torsion angles from NMR data. J. Biomol. NMR. 2002, 24, 339-349. (d) Neidig, K.-P.; Geyer, M.; Goerler, A.; Antz, C.; Saffrich, R.; Beneicke, W.; Kalbitzer, H. R. Aurelia, a program for computer aided analysis of multidimensional NMR spectra. J. Biomol. NMR. 1995, 6, 255-270.
8. 1H NMR Data. Tetrahedron Comput. Method. 1990, 3, 113-118. (c) Padrta, P.; Sklenár, V. Program Mulder - A tool for extracting torsion angles from NMR data. J. Biomol. NMR. 2002, 24, 339-349. (d) Neidig, K.-P.; Geyer, M.; Goerler, A.; Antz, C.; Saffrich, R.; Beneicke, W.; Kalbitzer, H. R. Aurelia, a program for computer aided analysis of multidimensional NMR spectra. J. Biomol. NMR. 1995, 6, 255-270.
9. Díez, E.; San-Fabian, J.; Guilleme, J.; Altona, C.; Donders L. A. Vicinal Proton-Proton Coupling Constants I. Formulation of an Equation Including Interactions Between Substituents. Mol. Phys. 1989, 68, 49-63.
10. (a) Pachler, K. G. R. Extended Hückel Theory MO Calculations of Proton-Proton Coupling Constants II. The Effect of Substituents on Vicinal Couplings in Monosubstituted Ethanes. Tetrahedron 1971, 27, 187-199.
11. (b) Pachler, K. G. R. The Dependence of Vicinal Proton-Proton Coupling Constants on Dihedral Angle and Substituents. J. Chem. Soc., Perkin Trans. 2 1972, 1936-1940.
12. Huggins, M, L. Bond Energies and Polarities. J. Am. Chem. Soc. 1953, 75, 4123-4126.
13. Marshall, J. L.; Walter, S. R.; Barfield, M.; Marchand, A. P.; Marchand N. W.; Segre, A. L. Reasons for the non equivalence of exo-exo and endo-endo vicinal NMR coupling constants in norbornanes. Tetrahedron 1976, 32, 537-542.
14. Donders, L. A.; de Leeuw, F. A. A. M.; Altona, C. Relationship Between Proton-Proton NMR Coupling Constants and Substituent Electronegativities IV. An Extended Karplus Equation Accounting for Interactions Between Substituents and its Application to Coupling Constant Data Calculated by the Extended Hückel Method. Magn. Reson. Chem. 1989, 27, 556-563.
15. Allinger, N. L. Quantum Chemistry Program Exchange MMP(85). Indiana State University. 1985.
16. (a) Colucci, W. J.; Jungk, S. J.; Gandour, R. D. An Equation Utilizing Empirically Derived Substituent Constants for the Prediction of Vicinal Coupling Constants in Substituted Ethanes, Magn. Reson. Chem. 1985, 23, 335-343.
17. (b) Colucci, W. J.; Gandour, R. D.; Mooberry, E. A. Conformational Analysis of Charged Flexible Molecules in Water by Application of a New Karplus Equation Combined with MM2 Computations: Conformations of Carnitine and Acetylcarnitine. J. Am. Chem. Soc. 1986, 108, 7141-7147.
18. 1H Coupling Constants. J. Am. Chem. Soc. 1992, 114, 1574-1581.
19. 3 equation. Magn. Reson. Chem. 1993, 31, 696-697.
20. Gil, V. M. S.; Varandas A. J. C. The Use of Vicinal H-H Coupling Constants in Rotational Isomerism Studies, I. J. Magn. Reson. 1981, 43, 28-39.
21. It is possible however, to run efficiently MestRe-J under 1386-Linux using the wine emulator: http://www.winehq.com.
22. Microsoft. Microsoft Visual C++ Class Library Reference.
23. http://www.codeproject.com.