Effect of neighbouring amide group bulkiness on anchimerically assisted ether bond cleavage: Part 7 | Zendy

Arcelli Antonio | Zendy; Porzi Gianni | Zendy; Rinaldi Samuele | Zendy; Sandri Sergio | Zendy

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Effect of neighbouring amide group bulkiness on anchimerically assisted ether bond cleavage: Part 7

Author(s) -

Arcelli Antonio,

Porzi Gianni,

Rinaldi Samuele,

Sandri Sergio

Publication year - 2004

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.726

Subject(s) - chemistry , hydrolysis , ether , amide , ether cleavage , vicinal , peptide bond , leaving group , bond cleavage , medicinal chemistry , stereochemistry , organic chemistry , enzyme , catalysis

The effect of the bulkiness of the amide group vicinal to the ether bond on the acid hydrolysis rate of substrates 1b – d was investigated. The kinetic data showed that 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 is proposed for 1d , which is supported by the thermodynamic activation parameters values. The hydrolysis rate of 1d is about 3 × 10 5 ‐fold higher than that of the reference compound. Copyright © 2004 John Wiley & Sons, Ltd.

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