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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > June  >
In the Laboratory
Advanced Chemistry Classroom and Laboratory
A Simple and Convenient Method for Generation and NMR Observation of Stable Carbanions
An Advanced Undergraduate Laboratory Experiment
Hamid S. Kasmai
Department of Chemistry, East Tennessee State University, Johnson City, TN 37614
Cover
June 1999
Vol. 76 No. 6
p. 830
Abstract
A simple and convenient method for the generation and NMR study of stable carbanions is described. Cyclopentadienide, indenide, fluorenide, xanthenide-d1, thioxanthenide-d1, 9,10-dihydroanthracenide-d3, and imidazolide anions were prepared from their corresponding conjugate acid progenitors in K+DMSYL-d6–/DMSO-d6 base/solvent system and their 1H and 13C NMR spectra were recorded. The data and sample spectra illustrate that reliable and good quality NMR spectra of stable carbanions may be obtained using simple laboratory setups and NMR instruments operating at 90 MHz or lower frequencies. The experiments described provide a good opportunity for students to apply the basic principles of 1H and 13C NMR spectrometry and the interesting topic of the exchange phenomenon in NMR. In addition, a study of acidities of carbon acids, calculations of electron and charge densities of carbanions, and the study of the correlation between the calculated charge densities and recorded NMR chemical shifts may be integrated into these activities.
More Information
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Citation
Kasmai, Hamid S. J. Chem. Educ. 1999, 76, 830.
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Keywords
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History
Created:
Last Updated:
6/11/2008
6/13/2008
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