title: Rapid quantification of the activating effects of hydrogen-bonding catalysts with a colorimetric sensor.
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.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Phuong N H
authors.initials: PN
authors.lastname: Huynh
authors.forename: Ryan R
authors.initials: RR
authors.lastname: Walvoord
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D002384:Catalysis; D003124:Colorimetry / Q000295:instrumentation*; D006860:Hydrogen Bonding