The reactions of benzoate esters are impacted mechanistically by the substituents on the substrate and the identity of the nucleophile. This study examined the transesterification of para-nitrophenyl benzoates, which were prepared from the reaction between para-nitrophenol and benzoyl chlorides bearing substituents in the meta or para positions. Alkoxides varying in steric bulk were used in subsequent transesterification. The change in absorbance as a function of time was monitored by UV/Vis in order to determine the apparent rate constant. The formulation of a Hammett plot from these data gives insight into the sensitivity of transesterification to substituent effects. It also illustrates the impact of sterics on the location of the transition state on the reaction coordinate.

Hammett study of the transesterification of para-nitrophenyl benzoates

247th National Meeting (2014)

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