Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents

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The kinetics of reactions of 1-chloro-2,4-dinitrobenzene with aniline and several substituted aromatic amines, B, in toluene shows a quadratic dependence of the second-order rate constant, kA, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reactio...

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Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Alvaro, Cecilia Elisabeth Silvana, Savini, M., Nicotra, V., Yankelevich, J.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1999
Acceso en línea:Registro en Scopus
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100 1 |a Nudelman, N.S. 
245 1 0 |a Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents 
260 |c 1999 
270 1 0 |m Nudelman, N.S.; Depto. de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar 
504 |a Nudelman, N.S., (1996) The Chemistry of Amino, Nitroso, Nitro and Related Groups, , (S. Patai, Ed.), Chap. 26. Wiley, Chichester 
504 |a Terrier, F., (1991) Organic Nitro Chemistry Series, , (H. Ferrer, Ed.) VCH Publishers, New York 
504 |a Bunnett, J.F., Cartano, A.V., (1981) J. Am. Chem. Soc., 103, p. 4861 
504 |a Bunnett, J.F., Sekiguchi, S., Smith, L.A., (1981) J. Am. Chem. Soc., 103, p. 4865 
504 |a Sekiguchi, S., Bunnett, J.F., (1981) J. Am. Chem. Soc., 103, p. 4871 
504 |a Forlani, L., (1996) The Chemistry of Amino, Nitroso, Nitro and Related Groups, , (S. Patai, Ed.), Chap. 10. Wiley, Chichester 
504 |a Durantini, E., Zingaretti, L., Anunziata, J.D., Silber, J.J., (1992) J. Phys. Org. Chem., 5, p. 557. , and references therein 
504 |a Nudelman, N.S., (1989) J. Phys. Org. Chem., 2, p. 1 
504 |a Reichardt, C.F., (1988) Solvents and Solvent Effects in Organic Chemistry, 2nd Ed., , VCH, Weinheim 
504 |a Headley, A.D., Strarness, S.D., Cheung, E.T., Malone, P.L., (1995) J. Phys. Org. Chem., 8, p. 26 
504 |a Gupta, S., (1987) Chem. Rev., 87, p. 1183 
504 |a Nudelman, N.S., Alvaro, C.E.S., Yankelevich, J.S., (1997) J. Chem. Soc., Perkin Trans. 2, p. 2125 
504 |a Nudelman, N.S., Palleros, D.R., (1983) J. Org. Chem., 48, p. 1613 
504 |a Nudelman, N.S., Savini, M., Alvaro, C.E.S., Nicotra, V., Yankelevich, J.S., (1999) J. Chem. Soc., Perkin Trans. 2, , in press 
504 |a Forlani, L., (1982) Gazz. Chim. Ital., 112, p. 205 
504 |a Nudelman, N.S., Marder, M., Gurevich, G., (1993) J. Chem. Soc., Perkin Trans. 2, p. 229. , and references therein 
504 |a Mancini, P.M.E., Martinez, R.D., Vottero, L.R., Nudelman, N.S., (1984) J. Chem. Soc., Perkin Trans. 2, p. 1133 
504 |a Martinez, R.D., Mancini, P.M.E., Vottero, L.R., Nudelman, N.S., (1986) J. Chem. Soc., Perkin Trans. 2, p. 1427 
504 |a Nudelman, N.S., Monserrat, J.M., (1990) J. Chem. Soc., Perkin Trans. 2, p. 1073 
504 |a Nudelman, N.S., Palleros, D.R., (1983) J. Org. Chem., 48, p. 1607 
504 |a Nagy, O.A., (1985) Bull. Soc. Chim. Belg., 94, p. 11 
504 |a Bernasconi, C.F., Zollinger, H., (1966) Helv. Chim. Acta, 49, p. 2570 
504 |a Bernasconi, C.F., Kaufmann, M., Zollinger, H., (1966) Helv. Chim. Acta, 49, p. 2563 
504 |a Ross, S.D., (1969) Tetrahedron, 25, p. 4427 
504 |a Wade L.G., Jr., (1993) Organic Chemistry, 2nd. Ed., , Prentice Hall, México 
504 |a Cattana, R.I., Singh, J.O., Anunziata, J., Silber, J.J., (1987) J. Chem. Soc., Perkin Trans. 2, p. 79 
504 |a Hirst, J., Onuoha, G.N., Onyido, I., (1988) J. Chem. Soc., Perkin Trans. 2, p. 971 
504 |a Hirst, J., (1995) J. Phys. Org. Chem., 7, p. 68 
506 |2 openaire  |e Política editorial 
520 3 |a The kinetics of reactions of 1-chloro-2,4-dinitrobenzene with aniline and several substituted aromatic amines, B, in toluene shows a quadratic dependence of the second-order rate constant, kA, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reaction with N-methylaniline shows a linear dependence of kA vs [B]. All these results are interpreted by the "dimer nucleophile" mechanism, and confirmed by the effects of a non-nucleophilic hydrogen bond acceptor tertiary amine which show the relevance of the structure of the nucleophile and the role of mixed aggregates in defining the mechanisms of aromatic nucleophilic substitutions with amines in aprotic solvents.  |l eng 
593 |a Depto. de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina 
593 |a Departamento de Quimica, Facultad de Ingeniería, Universidad Nacional del Comahue, Neuquén, Argentina 
690 1 0 |a AMINE AGGREGATION STATES 
690 1 0 |a APROTIC SOLVENTS 
690 1 0 |a AROMATIC NUCLEOPHILIC SUBSTITUTIONS 
690 1 0 |a DIMER NUCLEOPHILE MECHANISM 
690 1 0 |a NUCLEOPHILE STRUCTURE 
690 1 0 |a REACTION KINETICS 
690 1 0 |a REACTION MECHANISM 
700 1 |a Alvaro, Cecilia Elisabeth Silvana 
700 1 |a Savini, M. 
700 1 |a Nicotra, V. 
700 1 |a Yankelevich, J. 
773 0 |d 1999  |g v. 64  |h pp. 1583-1593  |k n. 1  |p Collect. Czech. Chem. Commun.  |x 00100765  |w (AR-BaUEN)CENRE-3052  |t Collection of Czechoslovak Chemical Communications 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00100765_v64_n1_p1583_Nudelman  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00100765_v64_n1_p1583_Nudelman  |y Registro en la Biblioteca Digital 
961 |a paper_00100765_v64_n1_p1583_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 63469 

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