Reactivity of acetates in aqueous alcohols

Scientific paper - Preliminary note / Short communication

• Author: Bernard Denegri
• Author: Olga Kronja
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of organic chemistry)
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract (english)

A series of X,Y-substituted benzhydryl acetates (1-3) were subjected to solvolysis in various binary methanol/water and ethanol/water mixtures at 25 °C. The LFER equation log k = sf(Ef + Nf) was used
to derive the nucleofuge-specific parameters (Nf and sf) for an SN1 type reaction in 60 % and 80 % aqueous methanol. It has been established that X,Y-substituted benzhydryl acetates produce almost parallel correlation lines, so the average sf = 0.9 has been taken for calculation of the nucleofugality parameters
from a single rate constant in some solvent mixtures. In comparison with other leaving groups for which
the nucleofugality has already been determined, acetates are the poorest nucleofuges.

• Keywords (english): acetate; nucleofugality; electrofugality; solvolysis; nucleophilic substitution
• Language: english
• Publication type: Scientific paper - Preliminary note / Short communication
• Publication status: Published
• Peer review: Peer review - international
• Publication version: Published version
• Journal title: Croatica Chemica Acta
• Numbering: vol. 83, no. 2, pp. 223-226
• p-ISSN: 0011-1643
• e-ISSN: 1334-417X
• URN:NBN: urn:nbn:hr:163:107556
• Publication: 2010
• Document URL: https://hrcak.srce.hr/56026
• Type of resource: Text
• Access conditions: Open access
• Created on: 2020-04-17 16:48:17