Theoretical estimation of the annular tautomerism of indazoles

Journal of Physical Organic Chemistry

Volumn 18, Issue 8, 2005, Pages 719-724

  Alkorta, Ibon ^a   Elguero, José ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

AM1; B3LYP; Free Wilson models; Indazole; Tautomerism

Indexed keywords

CORRELATION METHODS; DENSITY (SPECIFIC GRAVITY); ENERGY GAP; ENTHALPY; FREE RADICALS; HARMONIC ANALYSIS; MOLECULAR DYNAMICS;

AM1; B3LYP; FREE-WILSON MODELS; INDAZOLE; TAUTOMERISM;

AROMATIC COMPOUNDS;

EID: 22544476260     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.923     Document Type: Review

References (38)

1. Minkin VI, Garnovskii DG, Elguero J, Katritzky AR, Denisko OV. Adv. Heterocycl. Chem. 2000; 76: 157-323 (see 175-176).
2. Catalan J, de Paz JLG, Elguero J. J. Chem. Soc., Perkin Trans. 2 1996; 57-60.
3. Ögretir C, Kaypak NF. THEOCHEM 2002; 583: 137-144;
4. Ögretir C, (Kaypak) Tay NF. THEOCHEM 2002; 583: 145-153.
5. Borges F, Fernandes E, Roleira F. Curr. Med. Chem. 2002; 9: 195-217.
6. Elnagdy MH, Elmoghayar MRH. Adv. Heterocycl. Chem. 1987; 41: 319-376.
7. Korpi ER, Uusi-Oukari M, Wegelius K. Eur. J. Pharmacol. 1992; 213: 323-329.
8. Catalán J, Claramunt RM, Elguero J, Laynez J, Menéndez M, Anvia F, Quian JH, Taagepera M, Taft RW. J. Am. Chem. Soc. 1998; 110: 4105-4111.
9. García MA, López C, Claramunt RM, Kenz A, Pierrot M, Elguero J. Helv. Chim. Acta 2002; 85: 2763-2776.
10. Glaser R, Mummert CL, Horan CJ, Barnes CL. J. Phys. Org. Chem. 1993; 6: 201-214.
11. Ballesteros P, Elguero J, Claramunt RM, Faure R, Foces-Foces C, Hernández-Cano F, Rousseau A. J. Chem. Soc., Perkin Trans. 2 1986; 1677-1681;
12. Schilf W, Stefaniak L, Witanowski M, Webb GA, Braun S. Pol. J. Chem. 1986; 60: 151-155;
13. Schilf W, Stefaniak L, Webb GA. Magn. Reson. Chem. 1987; 25: 721-724.
14. Faure R, Llinares J, Elguero J, Goya P. Bull. Soc. Chim. Belg. 1987; 96: 603-617;
15. Claramunt RM, Sanz D, López C, Jiménez JA, Jimeno ML, Elguero J, Fruchier A. Magn. Reson. Chem. 1997; 35: 35-76.
16. López C, Claramunt R, Trofimenko S, Elguero J. Can. J. Chem. 1993; 71: 679-684.
17. Chem3D Pro, Version 4.0. CambridgeSoft: Cambridge, 1997.
18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98. Gaussian: Pittsburgh, PA, 1998.
19. Becke AD. J. Chem. Phys. 1993; 98: 5648-5652;
20. Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785-789.
21. Hariharan PA, Pople JA. Theor. Chim. Acta 1973; 28: 213-222.
22. Pople JA, Krishnan R, Schlegel HB, Binkley JS. Int. J. Quantum Chem. Symp. 1979; 13: 225-241;
23. Saxe P, Yamaguchi Y, Schaefer HF. J. Chem. Phys. 1982; 77: 5647-5654.
24. Frisch MJ, Pople JA, Krishnam R, Binkley JS. J. Chem. Phys. 1984; 80: 3265-3269.
25. Curtiss LA, Raghavachari K, Trucks GW, Pople JA. J. Chem. Phys. 1991; 94: 7221-7230;
26. Curtiss LA, Raghavachari K, Trucks GW, Pople JA. J. Chem. Phys. 1993; 98: 1293-1298;
27. Curtiss LA, Redfern PC, Smith BJ, Radom L. J. Chem. Phys. 1996; 104: 5148-5152.
28. Hansch C, Leo A. Exploring QSAR: Fundamentals and Applications in Chemistry and Biology. American Chemical Society: Washington, DC, 1995 (see http://www.chem.swin.edu.au/modules/mod4/qsarwebp6.html);
29. Cativiela C, Elguero J, Mathieu D, Meléndez E, Phan Tan Luu R. Eur. J. Med. Chem. 1983; 18: 359-363;
30. Cativiela C, García JI, Elguero J. An. Quím. 1987; 83C: 278-282;
31. Cativiela C, Elguero J, García JI, Mathieu D. QSAR Drug Des. Toxicol. 1987; 55-57;
32. Cativiela C, García JI, Elguero J, Mathieu D, Phan Tan Luu R. Quant. Struct.-Act. Relat. 1987; 6: 173-178;
33. Alkorta I, Elguero J, Rozas I, Balaban AT. THEOCHEM 1991; 228: 47-60.
34. Martínez A, Jimeno ML, Elguero J, Fruchier A. New J. Chem. 1994; 18: 269-277;
35. Ramos M, Alkorta I, Elguero J. Tetrahedron 1997; 53: 1403-1410;
36. Alkorta I, Elguero J. Struct. Chem. 1997; 8: 189-195.
37. Bader RFW. Atoms in Molecules: A Quantum Theory. Oxford University Press: New York, 1990.
38. Cabildo P, Claramunt RM, Elguero J. Org. Magn. Reson. 1984; 22: 603-607.