Abstract:
The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNC1B) were studied in several benzene-n-hexane mixtures at 40 °C in the presence of variable amounts of aniline. A linear dependence of the second-order rate coefficients, kA, with [B] is observed, with a null intercept. Taking into account the non-polar character of the solvent, and the excellent nucleofugacity of chlorine, this kinetic behaviour is interpreted as evidence of the aggregation of aniline, the hydrogen-bonded dimer acting as the nucleophile. Consistent with this interpretation, when the solvent is changed to THF, a good hydrogen-bond acceptor (HBA), the kA is no longer dependent on [B]. Electron donor-acceptor (EDA) molecular complexes of 2,4-DNC1B with benzene and with aniline, and also between aniline and the product, were clearly recognized and the stability constants of each one of these complexes were determined.
Registro:
| Documento: |
Artículo
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| Título: | Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| Autor: | Nudelman, N.S.; Savini, M.; Alvaro, C.E.S.; Nicotra, V.; Yankelevich, J. |
| Filiación: | Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Depto. de Quimica, Facultad de Ingeniería, Universidad Nacional del Comahue, Neuquén, Argentina
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| Año: | 1999
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| Número: | 8
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| Página de inicio: | 1627
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| Página de fin: | 1630
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| DOI: |
http://dx.doi.org/10.1039/a903559a |
| Título revista: | Journal of the Chemical Society. Perkin Transactions 2
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| Título revista abreviado: | J Chem Soc Perkin Trans 2
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| ISSN: | 03009580
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| CODEN: | JCPKB
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| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n8_p1627_Nudelman |
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Citas:
---------- APA ----------
Nudelman, N.S., Savini, M., Alvaro, C.E.S., Nicotra, V. & Yankelevich, J.
(1999)
. Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation. Journal of the Chemical Society. Perkin Transactions 2(8), 1627-1630.
http://dx.doi.org/10.1039/a903559a---------- CHICAGO ----------
Nudelman, N.S., Savini, M., Alvaro, C.E.S., Nicotra, V., Yankelevich, J.
"Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation"
. Journal of the Chemical Society. Perkin Transactions 2, no. 8
(1999) : 1627-1630.
http://dx.doi.org/10.1039/a903559a---------- MLA ----------
Nudelman, N.S., Savini, M., Alvaro, C.E.S., Nicotra, V., Yankelevich, J.
"Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation"
. Journal of the Chemical Society. Perkin Transactions 2, no. 8, 1999, pp. 1627-1630.
http://dx.doi.org/10.1039/a903559a---------- VANCOUVER ----------
Nudelman, N.S., Savini, M., Alvaro, C.E.S., Nicotra, V., Yankelevich, J. Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation. J Chem Soc Perkin Trans 2. 1999(8):1627-1630.
http://dx.doi.org/10.1039/a903559a
