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By C.H. Bamford and C.F.H. Tipper (Eds.)

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By C.H. Bamford and C.F.H. Tipper (Eds.)

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E. equivalent to the conditions above, gave almost the same rate, much slower than that obtained in the absence of the anhydride; addition of further amounts of anhydride produced a regular decrease in the rate. No satisfactory analysis has been made with acetyl nitrate but the qualitative retarding effect of addition of acetic anhydride' O 0 has been likewise interpreted as resulting from the preformation of dinitrogen pentoxide. 7 The kinetic importance of nitrous acid Nitrous acid can have both a catalytic and an anticatalytic effect on aromatic nitration, the former being appropriate in dilute (ca.

ArH ("C) 25 25 25 24 24 ? HNOj 30 25 25 25 25 24 24 25 25 25 25 25 25 24 24 ? 25 25 25 25 25 25 25 a Data refers to a 30 % solution of acid. Data refers to a 75 % solution of acid. 0b 28". 60b 24". lb 3 REACTIONS W I T H ELECTROPHILIC NITROGEN 35 all other conditions nitration involves “the formation of the active nitrating agent as the rate-determining step, and the interaction of aromatic substrates with the nitrating agent involves not free NO:, but a weaker electrophilic precursor of it, probably H’NO;”.

0 wt. 5 wt. % 3 25 REACTIONS W I T H ELECTROPHILIC NITROGEN H,S04). For the former compound the chloro substituent should increase the amount of free amine in solution and hence speed up the rate so that a significant difference in the relative rates in the two acid media should be observed if reaction occurs on the free amine; the relative rates were, however, 40 and 37. Hartshorn and Ridd4* showed that there is a negligible solvent isotope effect on nitrating anilinium ions in sulphuric acid and deuterated sulphuric acid (cf.

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