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- W2053436747 abstract "Lithiation of 1,4-bis(trifluoromethyl)benzene with lithium diisopropylamide in tetrahydrofuran at −78 °C occurs under conditions at which the rates of aggregate exchanges are comparable to the rates of metalation. Under such nonequilibrium conditions, a substantial number of barriers compete to be rate limiting, making the reaction sensitive to trace impurities (LiCl), reactant concentrations, and isotopic substitution. Rate studies using the perdeuterated arene reveal odd effects of LiCl, including catalyzed rate acceleration at lower temperature and catalyzed rate inhibition at higher temperatures. The catalytic effects are accompanied by corresponding changes in the rate law. A kinetic model is presented that captures the critical features of the LiCl catalysis, focusing on the influence of LiCl-catalyzed re-aggregation of the fleeting monomer that can reside above, at, or below the equilibrium population without catalyst." @default.
- W2053436747 created "2016-06-24" @default.
- W2053436747 creator A5039594674 @default.
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- W2053436747 creator A5048433983 @default.
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- W2053436747 creator A5088398282 @default.
- W2053436747 date "2015-05-06" @default.
- W2053436747 modified "2023-10-07" @default.
- W2053436747 title "Mechanism of Lithium Diisopropylamide-Mediated Ortholithiation of 1,4-Bis(trifluoromethyl)benzene under Nonequilibrium Conditions: Condition-Dependent Rate Limitation and Lithium Chloride-Catalyzed Inhibition" @default.
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- W2053436747 doi "https://doi.org/10.1021/jacs.5b01668" @default.
- W2053436747 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4788392" @default.
- W2053436747 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25900574" @default.
- W2053436747 hasPublicationYear "2015" @default.
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