| Abstract
| - To gain knowledge on the role played by the nature of the bridge interposed between hydroxyl andcarbonyl groups in esters of the title type, in principle able to hydrolyze through dissociativepathways via the conjugate base of the substrate (E1cB mechanism), we have studied the alkalinehydrolyses of 2,4-dinitrophenyl esters in which the π-system is a biphenyl, azobenzene, benzylideneaniline, or stilbene skeleton. Kinetic data, such as reactivity comparisons and Arrheniusparameters, show that these substrates react through the usual, associative, BAc2 mechanism. Thisoutcome is discussed and interpreted from both structural and energetic standpoints. The datasuggest that a value of 0.0 is the most appropriate assignment of the σp value for thebenzylidenamino substituent (C6H5CHN−).
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