The effect connected of the bulkiness of the amide group vicinal to the ether bond on the acid hydrolysis rate of some substrates was investigated. The kinetic data showed that the increased bulkiness of the acyl group has a considerable effect on the reaction rate, accelerating the anchimerically assisted hydrolytic process of the ether bond. A different mechanism, supported by the thermodynamic activation parameters values, is proposed for the pivaloyl amdide derivative. The hydrolysis rate of this compound is about 3.105 fold higher than that of the reference compound.
A. Arcelli, G. Porzi, S. Rinaldi, S. Sandri (2004). Effect of neighbouring amide group bulkiness on anchimerically assisted ether bond cleavage: Part 7. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 17, 289-293 [10.1002/poc.726].
Effect of neighbouring amide group bulkiness on anchimerically assisted ether bond cleavage: Part 7
ARCELLI, ANTONIO;PORZI, GIANNI;SANDRI, SERGIO
2004
Abstract
The effect connected of the bulkiness of the amide group vicinal to the ether bond on the acid hydrolysis rate of some substrates was investigated. The kinetic data showed that the increased bulkiness of the acyl group has a considerable effect on the reaction rate, accelerating the anchimerically assisted hydrolytic process of the ether bond. A different mechanism, supported by the thermodynamic activation parameters values, is proposed for the pivaloyl amdide derivative. The hydrolysis rate of this compound is about 3.105 fold higher than that of the reference compound.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
