Substituent and solvent effects on the proton transfer equilibrium in anils and azo derivatives of naphthol. Multinuclear NMR study and theoretical calculations

Journal of Molecular Structure

Volumn 705, Issue 1-3, 2004, Pages 1-9

  Alarcón, Sergio H ^a   Olivieri, Alejandro C ^a   Sanz, Dionisia ^b   Claramunt, Rosa M ^b   Elguero, José ^c  

^a UNIVERSIDAD NACIONAL DE ROSARIO   (Argentina)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

2 Hydroxynaphthalene 1 carbaldehyde; Azocompounds; Hydrogen bonded; NMR spectroscopy; Tautomeric equilibrium

Indexed keywords

2 NAPHTHOL; AZO COMPOUND; NAPHTHOL DERIVATIVE; SOLVENT;

AB INITIO CALCULATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; NITROGEN NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 4444255233     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-2860(03)00208-4     Document Type: Article

References (24)

1. Rozwadowski Z., Dziembowska T. Magn. Reson. Chem. 37:1999;274-278
2. Claramunt R.M., Sanz D., Alarcón S., Pérez Torralba M., Elguero J., Foces-Foces C., Pietrzak M., Langer U., Limbach H. Angew. Chem. Int. Ed. Engl. 40:2001;420-423
3. Sanz D., Pérez Torralba M., Alarcón S., Claramunt R.M., Foces Foces C., Elguero J. J. Org. Chem. 67:2002;462-1471
4. Claramunt R.M., López C., García M.A., Otero M.D., Torres M., Pinilla E., Alarcón S., Alkorta I., Elguero J. New. J. Chem. 25:2001;1061-1068
5. Alarcón S., Olivieri A. Recent Advances in Analytical Techniques. 1998;Gordon and Breach Science, Amsterdam. pp. 263-290
6. Zhuo J. Magn. Reson. Chem. 37:1999;259-268
7. Feringa B., Jager W., Lange B. Tetrahedron Lett. 49:1993;8267-8310
8. Gilli P., Bertolasi V., Pretto L., Lycka A., Gilli G. J. Am. Chem. Soc. 124:2002;13554-13567
9. Olivieri A., Wilson R., Paul I., Curtin D. J. Am. Chem. Soc. 111:1989;5525-5532
10. Alarcón S., Olivieri A., Jonsen P. J. Chem. Soc. Perkin Trans. 2:1993;1783-1786
11. Alarcón S., Olivieri A., Gonzalez-Sierra M. J. Chem. Soc. Perkin Trans. 2:1994;1067-1070
12. Kamienski B., Schilf W., Dziembowska T., Rozwadowski Z., Szady-Chemieniecka A. Solid State NMR. 16:2000;285-289
13. Antonov L., Fabian W., Nedeltcheva D., Kamounah F. J. Chem. Soc. Perkin Trans. 2:2000;1173-1179
14. Rozwadowski Z., Majewski E., Dziembowska T., Hansen P.E. J. Chem. Soc. Perkin Trans. 2:1999;2809-2817
15. Alarcón S., Olivieri A., Nordon A., Harris R. J. Chem. Soc. Perkin Trans. 2:1996;2293-2296
16. Alarcón S., Pagani D., Bacigalupo J., Olivieri A. J. Mol. Struct. 475:1999;233
17. Vargas V., Amigo L. J. Chem. Soc., Perkin Trans. 2:2001;1124-1129
18. Dziembowska Z., Rozwadowski E., Majewski E., Ambroziak K. Magn. Reson. Chem. 39:2001;484-488
19. Alarcón S., Olivieri A., Labadie G., Cravero R., Gonzalez-Sierra M. Tetrahedron Lett. 51:(16):1994;4619-4626
20. Braun S., Kalinowski H.-O., Berger S. 150 and more Basic NMR Experiments. 1998;Wiley, New York
21. Claramunt R.M., Sanz D., Santa María M.D., Gimenez J.A., Jimeno M.L., Elguero J. Heterocycles. 47:1998;301-314
22. Spartan Version 1.0.3, Wavefunction Inc, 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
23. Martin G.J., Martin M.L., Gouesnard J.-P. 15N-NMR Spectroscopy. 1981;Springer, New York
24. Berger S., Braun S., Kalinowski H.-O. NMR Spectrosocopy of the Non-Metallic Elements. 1996;Wiley, Chichester