1H and 13C NMR Determination of the β-Carbon and Proton in α,β,-Unsaturated Benzylidene Oxindoles

Abstract

<p>Determining the position of a β-carbon and proton in α,β-unsaturated benzylidene indolin-2-one molecules is complicated by various factors. E/Z isomerization is present in DMSO-d6, and resonance electronic effects are present which causes unique proton and carbon patterns to occur. Understanding the β-carbon is important for determining how relatively electrophilic the β-carbon will be when potentially undergoing a Michael attack by a cysteine sulfur atom. We also investigate how electron donating or electron withdrawing substituents on the geminal benzene ring will affect the β-carbon, and whether or not it is necessary to chromatographically isolate the isomers based on the molecules response to solution isomerization.</p><p>This presentation occurred at the Wright State University Campus-Wide Celebration of Research, Scholarship and Creative Activities on April 8, 2011</p>