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By Hoggett J.G.

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89. Proceedings of International Symposium, Warsaw (1963). London: Pergamon Press. (b) with Qureshi, E. A. & (in part) Gleghorn, J. T. (1968). J. chem. Soc. B, p. 312. 43. Gleghorn, J. , Moodie, R. B. & Schofield, K. (a) with Williamson, M. J. (1966). J. chem. Soc. B, p. 870; (b) with Qureshi, E. A. (1968). J. chem. Soc. B, p. 316. 44. Johnson, C. D. & Katritzky, A. R. (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.

Bricks, K. & de Vries, J. L. (1950). Acta crystallogr. 3, 290. 22. Hantzsch, A. (a) (1925). Ber. dt. chem. Ges. 58, 941; (1930) Z. phys. Chem. 149, 161. (6) (1908), Z. phys. Chem. 61, 257; Z. phys. Chem. 62, 178, 626; (1909), Z. phys. Chem. 65, 41; (1910), Z. phys. Chem. 68, 204. 23. (d) Saposchnikow, A. (190^), Z. phys. Chem. phys. Chem. 51, 609; (1905), Z. 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).

5. 2). 6 show that the rates of reaction of compounds such as phenol and i-napthol are equal to the encounter rate. This observation is noteworthy because it shows that despite their potentially very high reactivity these compounds do not draw into reaction other electrophiles, and the nitronium ion remains solely effective. These particular instances illustrate an important general principle: if by increasing the reactivity of the aromatic reactant in a substitution reaction, a plateau in rate constant for the reaction is achieved which can be identified as the rate constant for encounter of the reacting species, and if further structural modifications of the aromatic in the direction of further increasing its potential reactivity ultimately raise the rate constant above this plateau, then the incursion of a new ekctrophile must be admitted.

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Nitration and aromatic reactivity by Hoggett J.G.


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