PM3 Studies on the Acid-Catalyzed Hydrolysis of 1-Phenoxyethyl Propionate

Title
PM3 Studies on the Acid-Catalyzed Hydrolysis of 1-Phenoxyethyl Propionate
Authors
Kim, C.K.; Lee, B.S.
Keywords
CARBONYL GROUP, MECHANISM
Issue Date
1998-06-26
Publisher
Bulletin of the Korean Chemical Society
Abstract
Acid catalyzed hydrolysis of 1-phenoxyethyl propionate, I, has been studied using the PM3 method in the gas phase. The first step of the reaction is the protonation of basic sites, three different oxygens in I, producing three protonated species II, III and IV. Al possible reaction pathways have been studied from each protonated structure. Changes in the reaction mechanisms have also been discussed from the results obtained by varying a nucleophile from a water monomer to a water dimer to a complex between one water molecule and an intermediate product (propionic acid or phenol) produced in the preceding unimolecular dissociation processes. Minimum energy reaction pathway is 2-W among the possible pathways, in which water dimer acts as an active catalyst and therefore facilitates the formation of a six-membered cyclic transition state. Lower barrier of 2-W is ascribed to an efficient bifunctional catalytic effect of water molecules. PM3-SM3.1 single point calculations have been done at the gas-phase optimized structure (SM3.1/PM3//PM3) to compare theoretical results to those of experimental work.
URI
http://dspace.inha.ac.kr/handle/10505/20158
ISSN
0253-2964
Appears in Collections:
College of Natural Science(자연과학대학) > Chemistry (화학) > Journal Papers, Reports(화학 논문, 보고서)
Files in This Item:
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