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

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

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 us...

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Veröffentlicht in:Journal of chemical education 1996-06, Vol.73 (6), p.A124
Hauptverfasser: Manfredi, K. P, McGrew, L. A
Format: Artikel
Sprache:eng
Schlagworte:
Carbon
Carbon 13
Chloride
Climate
Hydrochloric acid
Inhalants
NMR
Nuclear magnetic resonance
Organic chemistry
Research Methodology
Steam
Vacuum distillation
Water
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Zusammenfassung: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed073pA124