Mechanism of the reactions of substituted anilines with phenyl 2,4,6-trinitrophenyl ether in benzene: evidence for a cyclic transition state involving an eight-membered ring
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1357-1360
- https://doi.org/10.1039/p29820001357
Abstract
Rates and activation parameters have been determined for the reactions of phenyl 2,4,6-trinitrophenyl ether with substituted anilines in benzene. For some of the nucleophiles, the rates decrease with increasing temperature in the range 5–35 °C resulting in negative activation enthalpies (ΔH‡–3.1 to –27.3 kJ mol–1). This is strong evidence for a stepwise mechanism involving (at least) a pre-equilibrium. These base-catalysed nucleophilic substitution reactions are sensitive to the nature of the arylated amine as indicated by the Hammett's constant (ρ–7.7).Keywords
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