Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation

Mostrar otras versiones (1)

The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNC1B) were studied in several benzene-n-hexane mixtures at 40 °C in the presence of variable amounts of aniline. A linear dependence of the second-order rate coefficients, kA, with [B] is observed, with a null intercept. Tak...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Savini, M., Alvaro, Cecilia Elisabeth Silvana, Nicotra, V., Yankelevich, J.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 1999
Acceso en línea:Registro en Scopus
DOI
Handle
Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
LEADER 05851caa a22006977a 4500
001 PAPER-2614
003 AR-BaUEN
005 20240927140934.0
008 190411s1999 xx ||||fo|||| 00| 0 eng|d
024 7 |2 scopus  |a 2-s2.0-0347025863 
030 |a JCPKB 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
100 1 |a Nudelman, N.S. 
245 1 0 |a Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation 
260 |b Royal Society of Chemistry  |c 1999 
270 1 0 |m Nudelman, N.S.; Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar 
504 |a Williams, D.H., Westwell, M.S., (1998) Chem. Soc. Rev., 27, p. 57 
504 |a Hobza, P., Zahradnik, R., (1988) Intermolecular Complexes, p. 25. , Elsevier, Amsterdam, Ch. I 
504 |a Nudelman, N.S., (1996) The Chemistry of Amino, Nitroso, Nitro and Related Groups, , Ch. 26, Ed. S. Patai, J. Wiley & Sons, London 
504 |a Terrier, F., (1991) Nucleophilic Aromatic Displacement: The Influence of the Nitro Group, in Organic Nitro Chemistry Series, , Ed. H. Ferrer, VCH Publishers, New York 
504 |a Nudelman, N.S., Palleros, D., (1981) Acta Sud. Am. Quim., 1, p. 125 
504 |a Nudelman, N.S., (1989) J. Phys. Org. Chem., 2, p. 1 
504 |a Nudelman, N.S., Alvaro, C.E.S., Yankelevich, J.S., (1997) J. Chem. Soc., Perkin Trans. 2, p. 2125. , and references therein 
504 |a Durantini, E., Zingaretti, L., Anunziata, J.D., Silber, J.J., (1992) J. Phys. Org. Chem., 5, p. 557 
504 |a Anunziata, J.D., Singh, J.O., Silber, J.J., (1981) Can. J. Chem., 38, p. 505 
504 |a Hirst, J., (1995) J. Phys. Org. Chem., 7, p. 68. , and references therein 
504 |a Palleros, D., Nudelman, N.S., (1985) J. Chem. Soc., Perkin Trans. 2, p. 479 
504 |a Forlani, L., (1984) J. Chem. Res (S), p. 260 
504 |a Cattana, R., Singh, J.O., Anunziata, J.D., Silber, J.J., (1987) J. Chem. Soc., Perkin Trans. 2, p. 79 
504 |a Forlani, L., Sintoni, M., Todesco, P.E., (1986) J. Chem. Res. (S), 66, p. 344 
504 |a Hirst, J., Onuoha, G.N., Onyido, I., (1988) J. Chem. Soc., Perkin Trans. 2, p. 971 
504 |a Nudelman, N.S., Marder, M., Gurevich, A., (1993) J. Chem. Soc., Perkin Trans. 2, p. 229 
504 |a Nudelman, N.S., Palleros, D.R., (1983) J. Org. Chem., 48, p. 1613 
504 |a Forlani, L., (1996) The Chemistry of Amino, Nitroso, Nitro and Related Groups, , Ch. 10, Ed. S. Patai, J. Wiley & Sons, London 
504 |a Sepulcri, P., Goumont, R., Hallé, J.-C., Buncel, E., Terrier, F., (1997) Chem. Commun., p. 789 
504 |a Bernasconi, C., Rossi, R.H., (1976) J. Org. Chem., 41, p. 44 
504 |a Kamlet, M., Abboud, J., Abraham, M., Taft, R., (1983) J. Org. Chem., 48, p. 2877 
504 |a Buncel, E., Norris, A., Russel, K., (1962) Rev. Chem. Soc., 22, p. 123 
504 |a Colter, A.K., Hui, S.H., (1968) J. Org. Chem., 33, p. 1935 
504 |a Forlani, L., Cimarelli, C., (1989) J. Phys. Org. Chem., 2, p. 653 
504 |a Singh, J.O., Anunziata, J.D., Silber, J.J., (1985) Can. J. Chem., 63, p. 903 
504 |a Chiachiera, S., Cattana, R., Singh, J.O., Anunziata, J.D., Silber, J.J., (1989) J. Phys. Org. Chem., 2, p. 631 
504 |a Mancini, P.M.E., Terenzani, A., Gasparri, M.G., Vottero, L.R., (1995) J. Phys. Org. Chem., 8, p. 617 
504 |a Forlani, L., (1982) Gazz. Chim. Ital., 112, p. 205 
504 |a Nudelman, N.S., Savino, M., Nicotra, V., Yankelevich, J.S., (1997) Anales Asoc. Quim. Argent., 85, p. 231 
506 |2 openaire  |e Política editorial 
520 3 |a The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNC1B) were studied in several benzene-n-hexane mixtures at 40 °C in the presence of variable amounts of aniline. A linear dependence of the second-order rate coefficients, kA, with [B] is observed, with a null intercept. Taking into account the non-polar character of the solvent, and the excellent nucleofugacity of chlorine, this kinetic behaviour is interpreted as evidence of the aggregation of aniline, the hydrogen-bonded dimer acting as the nucleophile. Consistent with this interpretation, when the solvent is changed to THF, a good hydrogen-bond acceptor (HBA), the kA is no longer dependent on [B]. Electron donor-acceptor (EDA) molecular complexes of 2,4-DNC1B with benzene and with aniline, and also between aniline and the product, were clearly recognized and the stability constants of each one of these complexes were determined.  |l eng 
593 |a Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina 
593 |a Depto. de Quimica, Facultad de Ingeniería, Universidad Nacional del Comahue, Neuquén, Argentina 
700 1 |a Savini, M. 
700 1 |a Alvaro, Cecilia Elisabeth Silvana 
700 1 |a Nicotra, V. 
700 1 |a Yankelevich, J. 
773 0 |d Royal Society of Chemistry, 1999  |h pp. 1627-1630  |k n. 8  |p J Chem Soc Perkin Trans 2  |x 03009580  |w (AR-BaUEN)CENRE-119  |t Journal of the Chemical Society. Perkin Transactions 2 
856 4 1 |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0347025863&doi=10.1039%2fa903559a&partnerID=40&md5=3ac595ea57b484a39c306ea10e100049  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1039/a903559a  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_Nudelman  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n8_p1627_Nudelman  |y Registro en la Biblioteca Digital 
961 |a paper_03009580_v_n8_p1627_Nudelman  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 63567 

Ejemplares similares