Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study

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An experimental study of the effects of intramolecular electric fields on 1J(C,H) coupling constants involving a formyl proton in a series of 5-X-salicylaldehydes is reported. The particularly large electric field component along the Cc-Hf bond, calculated for X = NO2, leads to a measured substituen...

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Autor principal: De Kowalewski, D.G
Otros Autores: Kowalewski, V.J, Peralta, J.E, Eskuche, G., Contreras, Rubén Horacio, Esteban, A.L, Galache, M.P, Díez, E.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1999
Acceso en línea:Registro en Scopus
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100 1 |a De Kowalewski, D.G. 
245 1 0 |a Intramolecular electric field effect on a 1J(C,H) NMR spin-spin coupling constant. An experimental and theoretical study 
260 |c 1999 
270 1 0 |m Esteban, A.L.; Depto. de Química Fisica, Facultad de Ciencias, Universidad de Alicante, Apartado 99, 03080-Alicante, Spain 
504 |a Vizioli, C., Ruiz De Azúa, M.C., Giribet, C.G., Contreras, R.H., Turi, L., Dannenberg, J.J., Rae, I.D., Lazzeretti, P., (1994) J. Phys. Chem., 98, p. 8858 
504 |a Giribet, C.G., Vizioli, C.V., Ruiz De Azúa, M.C., Contreras, R.H., Dannenberg, J.J., Masunov, A., (1996) J. Chem. Soc., Faraday Trans., 92, p. 3029 
504 |a Afonin, A.V., Vizioli, C., Ruiz De Azúa, M., Contreras, R.H., (1996) Bull Acad. Sci. Russia, Div. Chem. Sci., 45, p. 1362 
504 |a Afonin, A.V., Peruchena, N.M., Sosa, L., Contreras, R.H., (1997) Russ. Chem. Bull, 46, p. 251 
504 |a Satonaka, H., Abe, K., Hirota, M., (1988) Bull. Chem. Soc. Jpn., 61, p. 2031 
504 |a Afonin, A.V., Andriyankov, M.A., (1988) Zh. Org. Khim., 24, p. 1034 
504 |a Afonin, A.V., Sigalov, M.V., Korustova, S.E., Aliev, I.A., Vashchenko, V., Trofimov, B.A., (1990) Magn. Reson. Chem., 28, p. 580 
504 |a Green, R.D., (1974) Hydrogen Bonding by C-H Groups, , Macmillan, London 
504 |a Koch, U., Popelier, P.L.A., (1995) J. Phys. Chem., 99, p. 9747 
504 |a Schaefer, T., (1975) J. Phys. Chem., 79, p. 1888 
504 |a Reed, E., Curtis, L.A., Weinhold, F.A., (1988) Chem. Rev., 88, p. 899 
504 |a Frisch, M.J., Trucks, G.W., Schlegel, H.B., Gill, P.M.W., Johnson, B.G., Robb, M.A., Cheeseman, J.R., Pople, J.A., (1995) Gaussian 94, Revision D.4, , Gaussian, Pittsburgh, PA 
504 |a Pople, J.A., Beveridge, D.L., Dobosh, P.A., (1967) J. Chem. Phys., 47, p. 2026 
504 |a Pople, J.A., McIver, J.W., Ostlund, N.J., (1968) J. Chem. Phys., 49, p. 2960 
504 |a Ostlund, N.S., (1972) Quantum Chem. Prog. Exch., 9, p. 224 
504 |a Glendening, E.D., Reed, A.E., Carpenter, J.E., Weinhold, F., (1990) NBO Version 3.1 
504 |a Zürcher, R.F., (1967) Prog. Nucl. Magn. Reson. Spectrosc., 2, p. 205 
504 |a Grayson, M., Raynes, W.T., (1995) Magn. Reson. Chem., 33, p. 138 
504 |a Ernst, L., Wray, V., Chertkov, V.A., Sergeyev, N.M., (1977) J. Magn. Reson., 25, p. 123 
504 |a Bock, C.W., Hargittai, I., (1994) Struct. Chem., 5, p. 307 
504 |a Boykin, D.W., Chandrasekaran, S., Baumstark, A.L., (1993) Magn. Reson. Chem., 31, p. 489 
506 |2 openaire  |e Política editorial 
520 3 |a An experimental study of the effects of intramolecular electric fields on 1J(C,H) coupling constants involving a formyl proton in a series of 5-X-salicylaldehydes is reported. The particularly large electric field component along the Cc-Hf bond, calculated for X = NO2, leads to a measured substituent effect of 7.36 Hz. For other X substituents a linear correlation was found between the calculated substituent electric field component along the Cc-Hf bond and the substituent effect on 1J(Cc,Hf). To determine if 5-X substituents affect the intramolecular C=O⋯H-O hydrogen bond, NBO analyses were carried out on 5-NO2- and 5-H-salicylaldehyde, and they were compared with those corresponding to benzaldehyde and phenol. The effects of interactions other than the electrostatic one on 1J(Cc,Hf) couplings were ruled out. The experimental results are in agreement with theoretical predictions published previously. Copyright © 1999 John Wiley & Sons, Ltd.  |l eng 
593 |a Departamento de Física, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 1, (1428) Buenos Aires, Argentina 
593 |a Depto. de Química Fisica, Universidad de Alicante, 03080-Alicante, Spain 
593 |a Facultad de Ciencias C2-103, Univ. Autónome de Madrid, 28049-Madrid, Spain 
593 |a Depto. de Química Fisica, Facultad de Ciencias, Universidad de Alicante, Apartado 99, 03080-Alicante, Spain 
690 1 0 |a 5-X-SALICYLALDEHYDES 
690 1 0 |a 13C NMR 
690 1 0 |a 1J(C,H) 
690 1 0 |a INTRAMOLECULAR ELECTRIC FIELD 
690 1 0 |a NMR 
700 1 |a Kowalewski, V.J. 
700 1 |a Peralta, J.E. 
700 1 |a Eskuche, G. 
700 1 |a Contreras, Rubén Horacio 
700 1 |a Esteban, A.L. 
700 1 |a Galache, M.P. 
700 1 |a Díez, E. 
773 0 |d 1999  |g v. 37  |h pp. 227-231  |k n. 3  |p Magn. Reson. Chem.  |x 07491581  |w (AR-BaUEN)CENRE-972  |t Magnetic Resonance in Chemistry 
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963 |a VARI 

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