NDLI: Mechanistic aspects of superacid mediated condensation of polyphenols with ketones. Implications for polymer synthesis

Content Provider	Springer Nature Link
Author	López, Gustavo Cruz, Olivia H. Garza, Lilian I. Olvera Zolotukhin, Mikhail G. Fomine, Serguei
Copyright Year	2014
Abstract	A detailed computational study of possible reaction paths for methanesulfonic and triflic acid mediated polyhydroxyalkylation reaction between resorcinol and trifluoracetone accompanied by cyclodehydration to give 9H-xanthene containing polymers has been carried out at M06-2X/6-311+G** level of theory. A cluster solvation model was used for the calculations. The calculations revealed that the most kinetically favorable reaction path involves the cyclodehydration occurring during the polymer forming step. In this case 9H-xanthene formation is promoted by the activated phenyl ring in Wheland intermediate assisting the aromatic nucleophilic substitution of OH group which leads to the cyclization. It has been demonstrated that the inability of methanesulfonic acid to catalyze the formation of 9H-xanthene containing polymers is due to the very high barrier of the rate limiting step of the polymer forming reaction and not the cyclodehydration process.
Starting Page	1
Ending Page	9
Page Count	9
File Format	PDF
ISSN	16102940
Journal	Journal of Molecular Modeling
Volume Number	20
Issue Number	10
e-ISSN	09485023
Language	English
Publisher	Springer Berlin Heidelberg
Publisher Date	2014-10-09
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	DFT 9H-xanthene Hydroxyalkylation Protonation Superacid Trifluoromethyl group Computer Applications in Chemistry Molecular Medicine Computer Application in Life Sciences Characterization and Evaluation of Materials Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Physical and Theoretical Chemistry Computational Theory and Mathematics Catalysis Inorganic Chemistry Computer Science Applications

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