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• Alvaro, CE.S.
• Savini, MC.
• Nicotra, V
• Yankelevich, JS.
• Nudelman, NS.
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• Alvaro, CE.S.
• Savini, MC.
• Nicotra, V
• Yankelevich, JS.
• Nudelman, NS.
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• Alvaro, CE.S.
• Savini, MC.
• Nicotra, V
• Yankelevich, JS.
• Nudelman, NS.

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Molecules 2000, 5(3), 401-402; doi:10.3390/50300401

Article

Reaction of 2,4-Dinitrochlorobenzene with Aromatic Amines in Toluene: Effect of Nucleophile Structure

C. E.S. Alvaro ^1,* , M. C. Savini ¹ , V. Nicotra ¹ , J. S. Yankelevich ¹  and N. S. Nudelman ^2,*

¹ Dpto. de Química, Facultad de Ingeniería, Universidad Nacional del Comahue. Buenos Aires 1400. (8300) Neuquén, Argentina ² Dpto. de Química Orgánica. Facultad de Ciencias Exactas y Naturales. Pabellón II, 3°p, Ciudad Universitaria. U.B.A., Argentina

* Authors to whom correspondence should be addressed.

Published: 22 March 2000

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Abstract: The kinetics of the reaction of 2,4-dinitrochlorobenzene (DNClB) with aniline and substituted anilines such as p-anisidine, p-toluidine and N-methylaniline have been studied in toluene. Except for N-methylaniline the reactions have shown a third order in amine rate dependence which is consistent with aggregates of the amine acting as the nucleophile. On the other hand, the reaction of DNClB with N-methylaniline under the same conditions shows a linear dependence of the second order rate coefficient, k_A, vs [amine], which is consistent with the previous mechanism.

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