Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents

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The kinetics of the reaction between 1-chloro-2,4-dinitrobenzene and piperidine were studied in 2-methylpropan-1-ol, propan-1-ol, propan-2-ol, butan-2-ol, benzyl alcohol, 2-phenoxyethanol, 2-methoxyethanol, and diethylene glycol at 15, 25, and 40°C. The second-order rate coefficients, k <inf>A...

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Autor principal: Martinez, R.D
Otros Autores: Mancini, P.M.E, Vottero, L.R, Nudelman, N.S
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1986
Acceso en línea:Registro en Scopus
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100 1 |a Martinez, R.D. 
245 1 0 |a Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents 
260 |c 1986 
270 1 0 |m Nudelman, N.S.; Departmento de Química Orgánica, Facultad de Ciencias Exactes y Naturales, P. 3. Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
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 Taft, R.W., Abboud, J.-L., Kamlet, M.J., (1984) J. Org. Chem, 49, p. 2001 
504 |a Kamlet, M.J., Abboud, J.-L., Abraham, M.H., Taft, R.W., (1983) J. Org. Chem, 48, p. 2877 
504 |a Swain, C.G., (1984) J. Org. Chem, 49, p. 2005 
504 |a Swain, C.G., Swain, M.S., Powell, A.L., Alunni, S., (1983) J. Am. Chem. Soc, 105, p. 502 
504 |a Kamlet, M.J., Doherty, R., Taft, R.W., Abraham, M.H., (1983) J. Am. Chem. Soc, 105, p. 6741 
504 |a Frange, B., Abboud, J.-L.M., Benamou, C., Bellon, L., (1982) J. Org. Chem, 47, p. 4553 
504 |a Reichardt, C., Harbusch-Görnert, E., (1983) Liebigs Ann. Chem, p. 721 
504 |a Reichardt, C., (1979) Angew. Chem., Int. Ed. Engl, 18, p. 98 
504 |a Nudelman, N.S., Martinez, R.D., Mancini, P.M.E., Vottero, L.R., (1981) An. Soc. Cient. Argent, 211, p. 27 
504 |a Bernasconi, C.F., Gehriger, C.L., de Rossi, R.H., (1976) J. Am. Chem. Soc, 98, p. 8451 
504 |a Bernasconi, C.F., de Rossi, R.H., Gehriger, C.L., (1977) J. Am. Chem. Soc, 99, p. 4090 
504 |a Nudelman, N.S., Palleros, D., (1981) Acta Sudamericana Quím, p. 125 
504 |a Palleros, D., Nudelman, N.S., (1979) An. Soc. Cient. Argent, 207, p. 3 
504 |a Nudelman, N.S., Brieux, J.A., (1970) An. Asoc. Quim. Argent, 58, p. 207 
504 |a Nudelman, N.S., Brieux, J.A., (1970) An. Asoc. Quim. Argent, 58, p. 217 
504 |a Bunnett, J.F., Kato, T., Nudelman, N.S., (1969) J. Org. Chem, 34, p. 785 
504 |a Kamlet, M.J., Taft, R.W., (1982) J. Org. Chem, 47, p. 1734. , references therein 
504 |a Jorgensen, W.L., (1981) J. Am. Chem. Soc, 103, p. 341 
504 |a Sinsheimer, J.E., Kecehnelian, A.N., (1974) Anal. Chem, 46, p. 89 
504 |a Prahan, S.D., Mathews, H.B., (1978) Proc. Indian Acad. Sci., Sect. A, 87, p. 23 
504 |a Pople, J.A., Bernstein, H.J., Schneider, W.G., (1969) High Resolution NMR, , McGraw-Hill, New York 
504 |a Kern, M., Servois, D., Abello, L., Ponnetier, G., (1968) Bull. Soc. Chim. Fr, p. 2763 
504 |a Ponnetier, G., Abello, L., Bull. Soc. Chim. Fr, p. 1645 
504 |a Mateos, J.L., Cetina, R., Chao, O., (1965) Chem. Commun, p. 519 
504 |a Kamlet, M.J., Kayser, E.G., Jones, M.E., Abboud, J.-L.M., Eates, J.W., Taft, R.W., (1978) J. Chem. Phys, 82, p. 2477 
504 |a Taft, R.W., (1956) Steric Effects in Organic Chemistry, , M. S. Newman, Wiley, New York, ch. 13 
504 |a Kamlet, M.J., Kayser, E.G., Eates, J.W., Gilligan, W.H., (1973) J. Am. Chem. Soc, 95, p. 5210 
504 |a Bastianser, O., Kueseth, K., Mollendal, H., (1979) Topics Current Chem, 81, p. 101 
504 |a Marstokk, K.M., Mollendal, H., (1981) Acta Chem. Scand., Ser. A, 35, p. 395 
504 |a Hanif Aslam, M., Collier, G., Shorter, J., (1981) J. Chem. Soc., Perkin Trans. 2, p. 1572 
504 |a Koppel, I.A., Palm, V.A., (1967) Org. Reactivity, 4, p. 253 
504 |a Reynolds, W.F., Topsom, R.D., (1984) J. Org. Chem, 49, p. 1989 
504 |a Hoefnagel, A.J., Oesterbeek, W., Wepster, B.M., (1984) J. Org. Chem, 49, p. 1993 
504 |a Charton, M., (1984) J. Org. Chem, 49, p. 1997 
504 |a Vogel, A.I., (1972) Practical Organic Chemistry, , Longman, London 
520 3 |a The kinetics of the reaction between 1-chloro-2,4-dinitrobenzene and piperidine were studied in 2-methylpropan-1-ol, propan-1-ol, propan-2-ol, butan-2-ol, benzyl alcohol, 2-phenoxyethanol, 2-methoxyethanol, and diethylene glycol at 15, 25, and 40°C. The second-order rate coefficients, k <inf>A</inf>, for the reaction in these solvents are not well correlated with the previously found relationship between the parameter E<inf>T</inf>(30) and the k<inf>A</inf> values for reaction in aprotic non-hydrogen-bond donor solvents. 1 Inter- and intra-molecular hydrogen-bond interactions in the pure solvent and between the solvent and the amine are relevant in determining the reaction rate. The reactivity in hydroxylic solvents is inversely proportional to the hydrogen-bond-donating ability of the solvent. Fifteen (protic and aprotic) solvents are well correlated by Swain's parameters A and B, although caution is recommended when this linear free energy relationship is used.  |l eng 
593 |a Institute de Investigaciones de Productos Naturales, Análisis y Síntesis Orgánica IPNAYS CONICET-UNL, Santiago del Estero 2829, 3000 Santa Fe, Argentina 
593 |a Departmento de Química Orgánica, Facultad de Ciencias Exactes y Naturales, P. 3. Ciudad Universitaria, 1428 Buenos Aires, Argentina 
700 1 |a Mancini, P.M.E. 
700 1 |a Vottero, L.R. 
700 1 |a Nudelman, N.S. 
773 0 |d 1986  |h pp. 1427-1431  |k n. 9  |x 1472779X  |t Journal of the Chemical Society, Perkin Transactions 2 
856 4 1 |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-37049090646&doi=10.1039%2fP29860001427&partnerID=40&md5=d143065de5d86bfb995ccb1dd150d4bf  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1039/P29860001427  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_1472779X_v_n9_p1427_Martinez  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n9_p1427_Martinez  |y Registro en la Biblioteca Digital 
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