Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents

Mostrar otras versiones (1)

The kinetics of the reaction of 2,4-dinitrochlorobenzene with aniline have been studied in toluene and in toluene-methanol binary solvents and compared with the reactions in benzene and chloroform. The reactions in aprotic solvents exhibit a rate dependence that is third-order in amine consistent wi...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Alvaro, Cecilia Elisabeth Silvana, Yankelevich, J.S
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 1997
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 08038caa a22008657a 4500
001 PAPER-3179
003 AR-BaUEN
005 20240927140959.0
008 190411s1997 xx ||||fo|||| 00| 0 eng|d
024 7 |2 scopus  |a 2-s2.0-0009305317 
030 |a JCPKB 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
100 1 |a Nudelman, N.S. 
245 1 0 |a Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents 
260 |b Royal Society of Chemistry  |c 1997 
270 1 0 |m Nudelman, N.S.; Depto. de Química, Facultad de Ingeniería, Universidad Nacional del Comahue, Neuquén, Argentina 
504 |a Lambert, C., Von Schleyer, P.R., (1952) Methoden Org. Chem. (Houben-Weyl), 4th Ed, E19D, p. 1 
504 |a Trost, B.M., Fleming, I., (1991) Comprehensive Organic Synthesis, 1. , Pergamon Press, Oxford 
504 |a Nudelman, N.S., Lewkowicz, E., Furlong, J.J.P., (1993) J. Org. Chem., 58, p. 1847 
504 |a Decouzon, M., Gal, J.F., María, P.C., Raczynska, E.D., (1993) Rapid Commun. Mass Spectrom., 7, p. 599 
504 |a Koppel, I.A., Anvia, F., Taft, R.W., (1994) J. Phys. Org. Chem., 7, p. 717 
504 |a Berthelot, M., Helbert, M., Laurence, C., LeQuestel, J.Y., Anvia, F., Taft, R.W., (1993) J. Chem. Soc., Perkin Trans. 2, p. 625 
504 |a Koppel, I.A., Molder, U.H., Pikver, R.J., (1991) Electron and Proton Affinities of Molecules, pp. 5-112. , URSS Academy of Sciences Press, Ufa 
504 |a Meot-Ner, M., Sieck, L.W., (1991) J. Am. Chem. Soc., 113, p. 4448 
504 |a Bordwell, F.G., Hughes, D.L., (1986) J. Am. Chem. Soc., 108, p. 5991 
504 |a Gandler, J.R., Setiarahardjo, I.U., Tufon, C., Chen, C., (1992) J. Org. Chem., 57, p. 4169 
504 |a Reichardt, C.F., (1988) Solvents and Solvent Effects in Organic Chemistry, 2nd Edn., , VCH, Weinheim 
504 |a Koppel, I.A., Taft, R.W., Anvia, F., Zhu, S.Z., Hu, L.Q., Sung, K.S., DesMarteau, D.D., Maria, P.C., (1994) J. Am. Chem. Soc., 116, p. 3047 
504 |a Chechick, V.O., Bobylev, V.A., (1993) Zh Obshch, Khim., 63, p. 1502 
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 Jeffrey, G.A., Saenger, W., (1991) Hydrogen Bonding in Biological Molecules, , Springer-Verlag, Berlin-Heidelberg 
504 |a Tamaru, K., Ichikama, M., (1975) Catalysis by Electron-Donor-Acceptor Complexes, , Wiley, New York 
504 |a Nudelman, N.S., (1996) SNAr by Amines in Dipolar Aprotic Solvents in the Chemistry of Amino, Nitroso, Nitro and Related Groups, , ed. S. Patai, Wiley, Chichester, in press 
504 |a Forlani, L., Bosi, M., (1992) J. Phys. Org. Chem., 5, p. 429. , and references therein 
504 |a Durantini, E., Zingaretti, L., Anunziata, J.D., Silber, J.J.J., (1992) Phys. Org. Chem., 5, p. 557. , and references therein 
504 |a Forlani, L., (1982) Gazz. Chim. Ital., 112, p. 205 
504 |a Nudelman, N.S., Palleros, D.R., (1983) J. Org. Chem., 48, p. 1613 
504 |a Nudelman, N.S., Palleros, D.R., (1985) J. Chem. Soc., Perkin Trans. 2, p. 479 
504 |a Bunnett, J.F., Kato, T., Nudelman, N.S., (1974) Fundamental Organic Chemistry Laboratory Manual, p. 112. , ed. K. T. Finley and J. Wilson, Prentice-Hall, New Jersey 
504 |a Nudelman, N.S., Marder, M., Gurevich, A., (1993) J. Chem. Soc., Perkin Trans. 2, p. 229. , and references therein 
504 |a Nudelman, N.S., (1989) J. Phys. Org. Chem., 2, p. 1. , and references therein 
504 |a Hirst, J., (1995) J. Phys. Org. Chem., 7, p. 68. , and references therein 
504 |a Dixon, J.E., Bruice, T.C., (1972) J. Am. Chem. Soc., 94, p. 2052 
504 |a Nudelman, N.S., Palleros, D.R., (1983) J. Org. Chem., 48, p. 1607 
504 |a Nudelman, N.S., Montserrat, J., (1990) J. Chem. Soc., Perkin Trans. 2, p. 1073 
504 |a Terrier, F., Nucleophilic Aromatic Displacement: The influence of the nitro group (1991) Organic Nitro Chemistry Series, , ed. H. Ferrer, VCH Publishers, New York 
504 |a Chiacchiera, S.M., Singh, J.O., Anunziata, J.D., Silber, J.J., (1988) J. Chem. Soc., Perkin Trans. 2, p. 1585 
504 |a Bunnett, J.F., Morath, (1955) J. Am. Chem. Soc., 77, p. 5051 
504 |a Mancini, P.M., 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., Vottero, L.R., Nudelman, N.S., (1986) J. Chem. Soc., Perkin Trans. 2, p. 1427 
504 |a Mancini, P.M., Terenzani, A., Gasparri, M.G., Vottero, L.R., (1995) J. Phys. Org. Chem., 8, p. 617 
504 |a Nudelman, N.S., Savini, M., Nicotra, V., Yankelevich, J., unpublished work; Hirst, J., Onuoha, G.N., Onyido, Y., (1988) J. Chem. Soc., Perkin Trans. 2, p. 971 
504 |a Forlani, L., Todesco, P.E., (1980) Gazz. Chim. Ital., 100, p. 561 
504 |a V. Frena, G. Vivona, G. Consiglio and D. Spinelli, 1985, 2, 1865; Nudelman, N.S., Mancini, P.M., Martinez, R.D., Vottero, L.R., (1987) J. Chem. Soc., Perkin Trans. 2, p. 951 
504 |a Persson, J., Axelsson, S., Matsson, O., (1996) J. Am. Chem. Soc., 118, p. 20 
504 |a Johnson, J.E., Dutson, S.M., Dolliver, D.D., Todd, S.L., Hotema, M., (1995) J. Phys. Org. Chem., 8, p. 344 
504 |a Gesser, J.C., Zucco, C., Nome, F., (1995) J. Phys. Org. Chem., 8, p. 97 
504 |a Perepichka, I.F., Popov, A.F., (1995) J. Chem. Soc., Perkin Trans. 2, p. 3 
504 |a Perepichka, I.F., Popov, A.F., Kostenko, L.I., Artyomova, T.V., Kovac, J., (1988) Chemistry of Heterocyclic Compounds, p. 462. , ed. J. Kovác and P. Zálupsky, Elsevier, Amsterdam 
504 |a Perepichka, I.F., Kostenko, L.I., Popov, A.F., Chervinskii, A.Yu., (1988) Zh. Org. Khim., 24, p. 822 
506 |2 openaire  |e Política editorial 
520 3 |a The kinetics of the reaction of 2,4-dinitrochlorobenzene with aniline have been studied in toluene and in toluene-methanol binary solvents and compared with the reactions in benzene and chloroform. The reactions in aprotic solvents exhibit a rate dependence that is third-order in amine consistent with aggregates of the aniline acting as the nucleophile. Molecular complexes between the aniline and the substrate were also detected spectrophotometrically. Additionally, an inhibitory effect of toluene complexes was observed, which is similar to the previously reported effect of benzene in the reaction of the same substrate with n-butylamine. The reaction in the presence of pyridine shows an amine dependence which indicates formation of 'mixed aggregates' between aniline and pyridine. All the above results, as well as recently reported studies of other reactions different from SNAr, are fully interpreted within the 'dimer nucleophile' mechanism.  |l eng 
593 |a Depto. de Química, Facultad de Ingeniería, Universidad Nacional del Comahue, Neuquén, Argentina 
593 |a Depto. Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, P. 3, 1428 Buenos Aires, Argentina 
700 1 |a Alvaro, Cecilia Elisabeth Silvana 
700 1 |a Yankelevich, J.S. 
773 0 |d Royal Society of Chemistry, 1997  |h pp. 2125-2130  |k n. 10  |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-s2.0-0009305317&doi=10.1039%2fa607108b&partnerID=40&md5=5c0c16ae881ebc6138e7d430d9f17f9b  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1039/a607108b  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_03009580_v_n10_p2125_Nudelman  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n10_p2125_Nudelman  |y Registro en la Biblioteca Digital 
961 |a paper_03009580_v_n10_p2125_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 64132 

Ejemplares similares