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Abstract:

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 A, for the reaction in these solvents are not well correlated with the previously found relationship between the parameter ET(30) and the kA 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.

Registro:

Documento: Artículo
Título:Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents
Autor:Martinez, R.D.; Mancini, P.M.E.; Vottero, L.R.; Nudelman, N.S.
Filiación:Institute de Investigaciones de Productos Naturales, Análisis y Síntesis Orgánica IPNAYS CONICET-UNL, Santiago del Estero 2829, 3000 Santa Fe, Argentina
Departmento de Química Orgánica, Facultad de Ciencias Exactes y Naturales, P. 3. Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1986
Número:9
Página de inicio:1427
Página de fin:1431
DOI: http://dx.doi.org/10.1039/P29860001427
Título revista:Journal of the Chemical Society, Perkin Transactions 2
ISSN:1472779X
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n9_p1427_Martinez

Referencias:

  • Mancini, P.M.E., Martinez, R.D., Vottero, L.R., Nudelman, N.S., (1984) J. Chem. Soc., Perkin Trans. 2, p. 1133
  • Taft, R.W., Abboud, J.-L., Kamlet, M.J., (1984) J. Org. Chem, 49, p. 2001
  • Kamlet, M.J., Abboud, J.-L., Abraham, M.H., Taft, R.W., (1983) J. Org. Chem, 48, p. 2877
  • Swain, C.G., (1984) J. Org. Chem, 49, p. 2005
  • Swain, C.G., Swain, M.S., Powell, A.L., Alunni, S., (1983) J. Am. Chem. Soc, 105, p. 502
  • Kamlet, M.J., Doherty, R., Taft, R.W., Abraham, M.H., (1983) J. Am. Chem. Soc, 105, p. 6741
  • Frange, B., Abboud, J.-L.M., Benamou, C., Bellon, L., (1982) J. Org. Chem, 47, p. 4553
  • Reichardt, C., Harbusch-Görnert, E., (1983) Liebigs Ann. Chem, p. 721
  • Reichardt, C., (1979) Angew. Chem., Int. Ed. Engl, 18, p. 98
  • Nudelman, N.S., Martinez, R.D., Mancini, P.M.E., Vottero, L.R., (1981) An. Soc. Cient. Argent, 211, p. 27
  • Bernasconi, C.F., Gehriger, C.L., de Rossi, R.H., (1976) J. Am. Chem. Soc, 98, p. 8451
  • Bernasconi, C.F., de Rossi, R.H., Gehriger, C.L., (1977) J. Am. Chem. Soc, 99, p. 4090
  • Nudelman, N.S., Palleros, D., (1981) Acta Sudamericana Quím, p. 125
  • Palleros, D., Nudelman, N.S., (1979) An. Soc. Cient. Argent, 207, p. 3
  • Nudelman, N.S., Brieux, J.A., (1970) An. Asoc. Quim. Argent, 58, p. 207
  • Nudelman, N.S., Brieux, J.A., (1970) An. Asoc. Quim. Argent, 58, p. 217
  • Bunnett, J.F., Kato, T., Nudelman, N.S., (1969) J. Org. Chem, 34, p. 785
  • Kamlet, M.J., Taft, R.W., (1982) J. Org. Chem, 47, p. 1734. , references therein
  • Jorgensen, W.L., (1981) J. Am. Chem. Soc, 103, p. 341
  • Sinsheimer, J.E., Kecehnelian, A.N., (1974) Anal. Chem, 46, p. 89
  • Prahan, S.D., Mathews, H.B., (1978) Proc. Indian Acad. Sci., Sect. A, 87, p. 23
  • Pople, J.A., Bernstein, H.J., Schneider, W.G., (1969) High Resolution NMR, , McGraw-Hill, New York
  • Kern, M., Servois, D., Abello, L., Ponnetier, G., (1968) Bull. Soc. Chim. Fr, p. 2763
  • Ponnetier, G., Abello, L., Bull. Soc. Chim. Fr, p. 1645
  • Mateos, J.L., Cetina, R., Chao, O., (1965) Chem. Commun, p. 519
  • 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
  • Taft, R.W., (1956) Steric Effects in Organic Chemistry, , M. S. Newman, Wiley, New York, ch. 13
  • Kamlet, M.J., Kayser, E.G., Eates, J.W., Gilligan, W.H., (1973) J. Am. Chem. Soc, 95, p. 5210
  • Bastianser, O., Kueseth, K., Mollendal, H., (1979) Topics Current Chem, 81, p. 101
  • Marstokk, K.M., Mollendal, H., (1981) Acta Chem. Scand., Ser. A, 35, p. 395
  • Hanif Aslam, M., Collier, G., Shorter, J., (1981) J. Chem. Soc., Perkin Trans. 2, p. 1572
  • Koppel, I.A., Palm, V.A., (1967) Org. Reactivity, 4, p. 253
  • Reynolds, W.F., Topsom, R.D., (1984) J. Org. Chem, 49, p. 1989
  • Hoefnagel, A.J., Oesterbeek, W., Wepster, B.M., (1984) J. Org. Chem, 49, p. 1993
  • Charton, M., (1984) J. Org. Chem, 49, p. 1997
  • Vogel, A.I., (1972) Practical Organic Chemistry, , Longman, London

Citas:

---------- APA ----------
Martinez, R.D., Mancini, P.M.E., Vottero, L.R. & Nudelman, N.S. (1986) . Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents. Journal of the Chemical Society, Perkin Transactions 2(9), 1427-1431.
http://dx.doi.org/10.1039/P29860001427
---------- CHICAGO ----------
Martinez, R.D., Mancini, P.M.E., Vottero, L.R., Nudelman, N.S. "Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents" . Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1986) : 1427-1431.
http://dx.doi.org/10.1039/P29860001427
---------- MLA ----------
Martinez, R.D., Mancini, P.M.E., Vottero, L.R., Nudelman, N.S. "Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents" . Journal of the Chemical Society, Perkin Transactions 2, no. 9, 1986, pp. 1427-1431.
http://dx.doi.org/10.1039/P29860001427
---------- VANCOUVER ----------
Martinez, R.D., Mancini, P.M.E., Vottero, L.R., Nudelman, N.S. Solvent effects on aromatic nucleophilic substitutions. Part 4. Kinetics of the reaction of 1-chloro-2,4-dinitrobenzene with piperidine in protic solvents. 1986(9):1427-1431.
http://dx.doi.org/10.1039/P29860001427