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Abstract

Chemistry

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published: February 20th, 2020

DOI:

10.3791/60745

1Department of Chemistry & Biochemistry, Loyola University Chicago

Abstract

Lewis acid-activation of carbonyl-containing substrates is a fundamental basis for facilitating transformations in organic chemistry. Historically, characterization of these interactions has been limited to models equivalent to stoichiometric reactions. Here, we report a method utilizing in situ infrared spectroscopy to probe the solution interactions between Lewis acids and carbonyls under synthetically relevant conditions. Using this method, we were able to identify 1:1 complexation between GaCl3 and acetone and a highly ligated complex for FeCl3 and acetone. The impact of this technique on mechanistic understanding is illustrated by application to the mechanism of Lewis acid-mediated carbonyl-olefin metathesis in which we were able to observe competitive binding interactions between substrate carbonyl and product carbonyl with the catalyst.

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Keywords Lewis Pairs

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