Solvent effects on aromatic nucleophilic substitutions. Part 3.1 The kinetics of the reaction of 2,4-dinitrochlorobenzene with piperidine in aprotic solvents

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The kinetics of the reaction between 2,4-dinitrochlorobenzene and piperidine were studied in nitromethane, NN-dimethylformamide, ethyl acetate, dioxane, and 1,1,1 -trichloroethane at 15, 25, and 40 °C. This reaction was chosen as the simplest example of aromatic nucleophilic substitution. Different...

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Autor principal: Mancini, P.M.E
Otros Autores: Martinez, R.D, Vottero, L.R, Nudelman, N.S
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1984
Acceso en línea:Registro en Scopus
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100 1 |a Mancini, P.M.E. 
245 1 0 |a Solvent effects on aromatic nucleophilic substitutions. Part 3.1 The kinetics of the reaction of 2,4-dinitrochlorobenzene with piperidine in aprotic solvents 
260 |c 1984 
270 1 0 |m Nudelman, N.S.; Departamento de Qulmica Organica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Pab. 2, P. 3. Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Martinez, R.D., Mancini, P.M., Vottero, L.R., Nudelman, N.S., (1981) An. Soc Cient. Argent, 211, p. 27 
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504 |a Reichardt, C., (1979) Solvent Effects in Organic Chemistry, , Verlag Chemie, Weinheim 
504 |a Amis, E.S., (1965) Solvent Effects on Reaction Rates and Mechanisms, , Academic Press, New York 
504 |a Bernasconi, C.F., (1973) MTP Int. Series in Org. Chem, 1. , For recent reviews see, Series One, ed. H. Zollinger, Butterworths, London 
504 |a Nudelman, N.S., (1980) An. Acad. Nac Cienc. Exactas, Fis. Nat. Buenos Aires, 32, p. 109 
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504 |a Vottero, L.R., Mancini, P.M., Martinez, R.D., Nudelman, N.S., (1982) Acta Sudam Quim. (Chile), 2, p. 19 
504 |a Riddick, J.A., Bunger, W.B., (1970) Organic Solvents. Physical Properties and Methods of Purification, , Wiley-Interscience, New York, 3rd. edn 
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504 |a Palleros, D., Nudelman, N.S., (1980) An. Soc. Cient. Argent, 207, p. 3 
504 |a Reichardt, C., (1979) Angew. Chem., Int. Ed. Engl, 18, p. 98 
504 |a Kamlet, M.J., Taft, R.W., (1982) J. Org. Chem, 47, p. 1734. , references therein 
504 |a Shorter, J., (1973) Correlation Analysis in Organic Chemistry, 68p. , E.g, Clarendon Press, Oxford 
504 |a Barton, A., (1975) Chem. Rev, 75, p. 731 
504 |a Hildebrand, J.H., Scott, R.L., (1964) The Solubility of Nonelectrolytes, , Dover, New York, 3rd edn 
504 |a Kagiya, T., Sumida, Y., Inoue, T., (1968) Bull. Chem. Soc Jpn, 41, p. 767 
504 |a Chapman, N.B., Dack, M.R., Newman, D.J., Shorter, J., Wilkinson, R., (1974) J. Chem. Soc, Perkin Trans, 2, p. 962 
504 |a Gutmann, V., (1977) CHEMTECH, p. 255. , references cited therein 
504 |a Kosower, E.M., (1968) An Introduction to Physical Organic Chemistry, p. 30. , Wiley, New York 
504 |a Koppel, I.A., Palm, V.A., (1971) Reakts. Sposobn. Org. Soedin, 8, p. 291 
504 |a Koppel, A., Palm, V.A., (1974) Engl. Edn, 11, p. 137 
504 |a (1972) Advances in Linear Free Energy Relationships, , N. B. Chapman and J. Shorter, Plenum Press, New York, ch. 5 
504 |a Abraham, M.H., Kamlet, M.J., Taft, R.W., (1982) J. Chem. Soc, Perkin Trans, 2, p. 923 
504 |a Kamlet, M.J., Taft, R.W., Carr, P.W., Abraham, M.H., (1982) J. Chem. Soc, Faraday Trans, 1 (78), p. 1689 
504 |a Kamlet, M.J., Jones, M.E., Taft, R.W., Abboud, J.-L.M., (1979) J. Chem. Soc, Perkin Trans, 2, p. 342 
504 |a Aslam, M.H., Gollier, G., Shorter, J., (1981) J. Chem. Soc, Perkin Trans, 2, p. 1572. , preceding papers 
504 |a Kamlet, M.J., Carr, P.W., Taft, R.W., Abraham, M.H., (1981) J. Am. Chem. Soc, 103, p. 6062 
504 |a Fowler, F.W., Katritzky, A.R., Rutherford, R.J., (1971) J. Chem. Soc. B, p. 460 
504 |a Kryogowski, T.M., Fawcett, W.R., (1975) J. Am. Chem. Soc, 97, p. 2143 
504 |a Dougherty, R.C., (1975) Tetrahedron Lett, p. 385 
504 |a Mayer, V., (1978) Monatsh. Chem, 109 (421), p. 775 
504 |a Kamlet, M.J., Taft, R.W., (1979) J. Chem. Soc, Perkin Trans, 2, p. 337 
504 |a Martin, G.J., Martin, M.L., (1964) J. Chim. Phys, 61, p. 1222 
504 |a Ross, S.D., (1958) J. Am. Chem. Soc, 80, p. 5319 
504 |a Pietra, F., Vitali, D., (1968) J. Chem. Soc B, p. 1200 
504 |a Taft, R.W., Pienta, N.J., Kamlet, M.J., Arnett, E.M., (1981) J. Org. Chem, 46, p. 661 
504 |a Burden, A.G., Chapman, N.B., Duggua, H.F., Shorter, J., (1978) J. Chem. Soc, Perkin Trans, 2, p. 296 
504 |a Fawcett, W.R., Krygowski, T.M., (1975) Aust. J. Chem, 28, p. 2115 
504 |a Knauer, B.R., Napier, J.J., (1976) J. Am. Chem. Soc, 98, p. 4395 
504 |a Bunnett, J.F., Kato, T., Nudelman, N.S., Fundamental Organic Chemistry Laboratory Manual, 112p. , K. T. Finley and J. Silson, Prentice-Hall, New Jersey 
520 3 |a The kinetics of the reaction between 2,4-dinitrochlorobenzene and piperidine were studied in nitromethane, NN-dimethylformamide, ethyl acetate, dioxane, and 1,1,1 -trichloroethane at 15, 25, and 40 °C. This reaction was chosen as the simplest example of aromatic nucleophilic substitution. Different correlations of the second-order rate coefficients KA with several solvent parameters were examined for this and earlier work combining 13 aprotic solvents in all with a range of 43 units in the dielectric constants (ε) in the series. It was found that the ET(30) parameter is the most useful available measure of the solvent influence in the present reaction if hydrogen-bond donor (HBD) solvents are excluded; the deviation from linearity of these solvents is explained as arising from the highly exposed strong negative charge on Dimroth's betaine which gives a high ET value to HBD solvents. Conversely, the correlation is remarkably successful for the hydrogen-bond acceptor (HBA) solvents since the positive charge in the present reaction is buried similarly to that in the model solute, and the amine hydrogen of the zwitterionic intermediate, ZH, is strongly involved in an intramolecular hydrogen bond. Aliphatic, aromatic, and polychlorinated aliphatic solvents are all well correlated.  |l eng 
593 |a Institute de Investigaciones de Productos Naturales, Analisis Y Slntesis Organica IPNAYS (CONICET-UNLFIQ), Santiago del Estero 2829, 3000 Santa Fe, Argentina 
593 |a Departamento de Qulmica Organica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Pab. 2, P. 3. Ciudad Universitaria, 1428 Buenos Aires, Argentina 
700 1 |a Martinez, R.D. 
700 1 |a Vottero, L.R. 
700 1 |a Nudelman, N.S. 
773 0 |d 1984  |h pp. 1133-1138  |k n. 7  |x 1472779X  |t Journal of the Chemical Society, Perkin Transactions 2 
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