The theoretical determination of heats of formation, proton affinities and gas basicities of N and C-substituted pyrazoles: Analysis of the substituent effects on the gas-phase basicity

Journal of Molecular Structure: THEOCHEM

Volumn 497, Issue 1-3, 2000, Pages 241-266

  El Hammadi, A ^a   El Mouhtadi, M ^a  

^a FACULTÉ DES SCIENCES   (Morocco)

Author keywords

Ab initio; AMI; Basicity; Gas phase; Heat of formation; Proton affinity; Pyrazole; Pyridine; Pyrrole; Structure; Substitution effects

Indexed keywords

PYRAZOLE DERIVATIVE;

ALKALINITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENERGY; GAS; GEOMETRY; STRUCTURE ANALYSIS; THEORY; THERMODYNAMICS;

EID: 0034143232     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(99)00380-2     Document Type: Article

References (32)

1. J.L.M. Abboud J. Catalãn J. Elguero R.W. Taft J. Org. Chem. 53 1988 1137
2. R.W. Taft R.D. Topsom Prog. Phys. Org. Chem. 17 1990 159
3. J.L.M. Abboud P. Cabildo T. Cañada J. Catalãn R.M. Claramunt J.L. de Paz J. Elguero H. Homan R. Notario C. Toiron J.I. Yranzo J. Org. Chem. 14 1992 3939
4. R. Notario M. Herreros A. El Hammadi H. Homan J.L.M. Abboud J. Phys. Org. Chem. 7 1994 657
5. A. El Hammadi M. El Mouhtadi R. Notario J.L.M. Abboud J. Elguero J. Chem. Res. (M) 1995 1080
6. R.W. Taft R.D. Topsom Prog. Phys. Org. Chem. 16 1987 1
7. W.J. Here R. Ditchfield L. Radom J.A. Pople J. Am. Chem. Soc. 92 1970 4796
8. A. El Hammadi M. El Mouhtadi R. Notario A. Werner J. Elguero J. Chem. Soc. Perkin Trans. 2 1995 379
9. J. Catalan M. Mendez J. Laynez R.M. Claramunt M. Bruix J. de Mendoza J. Elguero J. Heterocyclic. Chem. 22 1985 997
10. D.J. De Frees A.D. Mclean J. Comp. Chem. 7 1987 321
11. J.E. De lBene I. Shavitt J. Phys. Chem. 94 1990 5514
12. A. Komornicki D.E. Dixon J. Phys. Chem. 97 1992 1087
13. M. Karapetiantz, Thermodynamique Chimique, Mir (Ed.), Mouscou, 1975.
14. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, J. Pople, gaussian 92 , Revision E.1 Gaussian, Inc., Pittsburgh, PA, 1992.
15. M.J.S. Dewar E.G. Zoebisch E.F. Healy J.J.P. Stewart J. Am. Chem. Soc. 107 1985 3902
16. ampac , version 2.15, Available from Quantum Chemistry Program Exchange (QCPE).
17. R. Fletcher M.J.D. Powell Comput. J. 6 1963 163
18. W.C. Davido Comput. J. 10 1968 406
19. J.C. Traeger R.G. McLonghlin J. Am. Chem. Soc. 103 1981 3647
20. O. Mó M. Yáñez A.L. Llamas-Saiz C. Foces-Foces J. Elguero Tetrahedron 25 1995 7045
21. L. Nygaard D. Christen J.T. Nielsen J. Pedersen O. Senerling E. Vestergaard G.O. Sorensen J. Mol. Struct. 22 1974 401
22. S. Blanco J.C. López J.L. Alonso O. Mó M. Yáñez N. Jagerovic J. Elguero J. Mol. Struct. 344 1995 241
23. A.L. Llamas-Saiz C. Foces-Foces O. Mó M. Yáñez J. Elguero J. Comput. Chem. 16 1995 263
24. J.M. Orza O. Mó M. Yáñez J. Elguero Spectrochim. Acta Part A 53 1997 1383
25. M. Begtrup P. Vedso Acta Chem. Scad. 50 6 1996 549
26. S.W. Bensen J. Phys. Chem. 85 1981 3375
27. J.A. Boatz M.S. Gordon J. Chem. Phys. 94 1981 3375
28. S.G. Lias J.E. Bartmess J.F. Liebman J.L. Holmes R.D. Levin W.G. Mallard J. Phys. Chem. Ref. Data 17 Suppl. 1 1988
29. J.E. Del Bene J. Comp. Chem 6 1985 296
30. R.M. Claramunt D. Sanz J. Catalán F. Fabiro N.A. Garcı́a C. Foces-Foces A.L. Llamas-Saiz J. Elguero J. Chem. Soc. Perkin Trans. 2 1993 1687
31. E.P. Hunter, S.G. Lias, submitted for publication.
32. M.J.S. Dewar W. Thiel J. Am. Chem. Soc. 99 1977 4907