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Preparation and Properties of a Stable Organic Cation: A Microscale Experiment for Organic Chemistry

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K. P. Manfredi and L. A. McGrew

University of Northern Iowa, Cedar Falls, IA 50614

J. Chem. Educ., 1996, 73 (6), p A124

DOI: 10.1021/ed073pA124

Publication Date (Web): June 1, 1996

Section:

History, Education, and Documentation

Abstract

This article describes the microscale synthesis and characterization of the flavylium cation. It is a suitable experiment for students in the second semester of organic chemistry laboratory. Crossed-Aldol condensation of salicylaldehyde with acetophenone, follwed by acid-catalyzed cyclization, is used to prepare the cation. It is characterized using 13C NMR spectroscopy. Students are assisted in assigning the resonances by the Mulliken charge distribution, obtained by semi-empirical MO calculations using SPARTAN (Wavefunction, Inc.). The cation is isolated as the stable ferrichloride salt.