Nitration and aromatic reactivity by Hoggett J.G.

By Hoggett J.G.

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A) with Ridgewell, B. J. & Viney, M. (1967). jf. chem. Soc. B, p. 1204; (b) with Viney, M. (1967). J. chem. Soc. B, p. i2i i; (c) with Shakir, N. & Viney, M. (1967). J. chem. Soc. 1213. 45. Utley, J. H. P. & Vaughan, T. A. (1968). J. chem. Soc. B, p. 196. 46. Gilow, H. M. & Walker, G. L. (1967). J. org. Chem. 32, 2580. 47. (a) Brickmann, M. & Ridd, J. H. (1965). J. chem. Soc. p. 6845. , Utley, J. H. , & Ridd, J. H. (1965). J. chem. Soc. p. 6851. (c) Modro, T. A. & Ridd, J. H. (1968). J. chem. Soc.

Phys. Chem. 53, 225. (b) Bergius, F. (1910). Z. phys. Chem. 72, 338. 24. Gillespie, R. , Hughes, E. , Ingold, C. K. & Peeling, E. R. A. (1950). J. chem. Soc. p. 2504. 25. Millen, D. J. (1950). J. chem. Soc. p. 2589. 26. Bennett, G. , Brand, J. C. D. & Williams, G. (1946). J. chem. Soc. P. 87527. Cox, E. , Jeffrey, G. A. & Truter, M. R. (1948). Nature, Lond. 162, 259. 28. Olah, G. A. & Kuhn, S. J. (1964). Friedel-Crafts and Related Reactions, vol. 3 (ed. G. A. Olah), p. 1427. New York: Interscience.

The rate equation can be written in two ways, as follows: rate = k2 [ArH][HNO3] = k'2 [ArH] [NO2+], and from the observed value546 of k2, the value of the true second-order rate coefficient, k'2, for the nitration of benzene at 25 0C in 68% sulphuric acid follows as c. 4 x io 6 1 mol"1 s"1. This value approaches quite closely the value (c. 57a In both media a limit was reached beyond which the introduction of further activating substituents did not increase the rate of nitration; this limit was identified as the rate of encounter of the nitronium ions and the aromatic molecules.

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