A DFT study of the formation of xanthydrol motifs during electrophilic poly(aryl ether ketone) synthesis
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- 作者：Sigismund T. A. G. Melissen ; Vincent Tognetti…
- 关键词：Friedel–Crafts reactions ; Density functional theory ; Poly(aryl ether ketones) ; ωB97X ; D ; Electrophilic aromatic substitution ; Stacking ; Xanthydrol ; Polymer defect ; Chain termination
- 刊名：Journal of Molecular Modeling
- 出版年：2016
- 出版时间：January 2016
- 年：2016
- 卷：22
- 期：1
- 全文大小：2,693 KB
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78.Anslyn EV, Dougherty DA (2006) Modern Physical Organic Chemistry. University Science, Sausalito (CA, USA) - 作者单位：Sigismund T. A. G. Melissen (1) (2) (3)
Vincent Tognetti (1)
Georges Dupas (1)
Julien Jouanneau (2)
Guillaume Lê (2)
Laurent Joubert (1)
1. Normandy University, COBRA UMR 6014 & FR 3038, Université de Rouen, INSA Rouen, CNRS, 1 rue Tesniére, 76821 Mont St Aignan, Cedex, France
2. Arkema CERDATO Laboratories, Route du Rilsan, 27470, Serquigny, France
3. Laboratoire de Chimie, UMR ENSL-CNRS 5182Université de Lyon, Université Claude Bernard Lyon 1, Ecole Normale Supérieure de Lyon, CNRS, 46 allée d’Italie, 69007, Lyon Cedex, France - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Computer Applications in Chemistry
Biomedicine
Molecular Medicine
Health Informatics and Administration
Life Sciences
Computer Application in Life Sciences - 出版者：Springer Berlin / Heidelberg
- ISSN：0948-5023
文摘
The reaction pathway of the cyclization of 2-phenoxybenzophenone into 9-phenyl-9H-xanthen-9-ol in the presence of acid and an excess of AlCl33 was studied using density functional theory. This type of reaction is known to occur during the Friedel–Crafts polycondensation of poly(aryl ether ketones) following the undesired benzoylation of nucleophilic positions ortho- to the growing polymer’s ether groups. The formed defect acts as an undesired terminator of the polymer chain, causing severe problems in the polymer’s melt state. A branched, multistep mechanism reminiscent of the Friedel–Crafts acylation reaction is discovered; the reaction starts with the protonation of the carbonyl oxygen, followed by intramolecular electrophilic attack on the carbonyl carbon that determines the turnover frequency of the catalytic cycle and ends by deprotonation of the Wheland intermediate.