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Issue 8, 1999
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Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation

Abstract

The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNClB) 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-DNClB 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.

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Article type: Paper
DOI: 10.1039/A903559A
Citation: J. Chem. Soc., Perkin Trans. 2, 1999,0, 1627-1630

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    Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation

    N. Sbarbati Nudelman, M. Savini, C. E. Silvana Alvaro, V. Nicotra and J. Yankelevich, J. Chem. Soc., Perkin Trans. 2, 1999, 0, 1627
    DOI: 10.1039/A903559A

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