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Kinetics and Mechanism of the Nitration of Chlorobenzene with Nitric Acid

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Abstract

The rate of homogeneous nitration of chlorobenzene with 70-90% nitric acid is proportional to the chlorobenzene concentration and activity of nitric acid. The existence of linear correlations between the rate constants k 2ap and the acidity function -H and between logk * 2ap values (calculated using NO2 + concentration) and the acidity function -(H R + logaH 2O) indicates that the nitrating species is nitronium ion generated by reaction of H3O+ with nitric acid monohydrate. Increase in the energy of activation with rise in water concentration is explained by increase of ΔH for equilibrium formation of nitronium ion.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 198013, Russia

    E. A. Veretennikov, B. A. Lebedev & I. V. Tselinskii

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  1. E. A. Veretennikov
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  2. B. A. Lebedev
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  3. I. V. Tselinskii
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Veretennikov, E.A., Lebedev, B.A. & Tselinskii, I.V. Kinetics and Mechanism of the Nitration of Chlorobenzene with Nitric Acid. Russian Journal of Organic Chemistry 37, 964–968 (2001). https://doi.org/10.1023/A:1012470315254

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