Kinetic and Theoretical Consideration of 3,4-and 3,5-Dimethoxybenzoyl Chlorides Solvolyses
- Authors
- Park, Kyoung-Ho; Kevill, Dennis N.
- Issue Date
- Oct-2013
- Publisher
- 대한화학회
- Keywords
- Dimethoxybenzoyl chloride; Extended Grunwald-Winstein equation; Resonance effect; Kinetic solvent isotope effect; Activation parameters
- Citation
- Bulletin of the Korean Chemical Society, v.34, no.10, pp 2989 - 2994
- Pages
- 6
- Indexed
- SCI
SCIE
SCOPUS
KCI
- Journal Title
- Bulletin of the Korean Chemical Society
- Volume
- 34
- Number
- 10
- Start Page
- 2989
- End Page
- 2994
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/26693
- DOI
- 10.5012/bkcs.2013.34.10.2989
- ISSN
- 0253-2964
1229-5949
- Abstract
- The solvolysis rate constants of 3,4- (1) and 3,5-dimethoxybenzoyl (2) chlorides were measured in various pure and binary solvents at 25.0 degrees C, and studied by application of the extended Grunwald-Winstein (G-W) equation, kinetic solvent isotope effect in methanolysis and activation parameters. The solvolysis of 1 was interpreted as the unimolecular pathway due to a predominant resonance effect from para-methoxy substituent like 4-methoxybenzoyl chloride (3), while that of 2 was evaluated as the dual mechanism, with unimolecular or bimolecular reaction pathway according to the character of solvent systems (high electrophilic/nucleophilic) chosen, caused by the inductive effect by two meta-methoxy substituents, no resonance one. In the solvolyses of 1 and 2 with two -OCH3 groups, the resonance effect of para-methoxy substituent is more important to decide the mechanism than the inductive effect with other corresponding evidences.
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