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Rapid quantification of the activating effects of hydrogen-bonding catalysts with a colorimetric sensor.

Journal of the American Chemical Society (2012-09-15)
Phuong N H Huynh, Ryan R Walvoord, Marisa C Kozlowski
ABSTRACT

A sensor has been developed to quickly and simply assess the relative reactivity of different hydrogen-bonding catalysts. Specifically, blue-shifts seen upon treatment of H-bonding catalysts with the colorimetric compound 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one correlate well to the K(eq) of binding to the sensor. The blue-shifts also show a high degree of correlation with relative rates in Diels-Alder reactions of methyl vinyl ketone and cyclopentadiene employing the H-bonding catalysts. The relevance of the sensor blue-shifts to the LUMO-lowering abilities of the H-bonding catalysts is discussed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
7-Methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one, ≥95%

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