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1999
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February
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In the Laboratory
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Microscale Synthesis and 1H NMR Analysis of Tetraphenylporphyrins
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RaeAnne E. Falvo, and Larry M. Mink
Department of Chemistry, California State University, San Bernardino, CA 92407
Diane F. Marsh
Department of Chemistry, Riverside Community College, Riverside, CA 92506
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February 1999
Vol. 76 No. 2
p. 237
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| Abstract |
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The synthesis of tetraphenylporphyrin, H2[TPP], and para-substituted tetraphenylporphyrins, H2[(p-X)4TPP], where X = CN, CH3, and OCH3, is easily accomplished using microscale glassware. The compounds are synthesized from inexpensive starting reagents. The synthesis of the porphyrins involves the condensation of pyrrole with the appropriate benzaldehydes, producing purple solids. It is accomplished within one 2 1/2 hour laboratory period. These porphyrin systems generate simple 1H NMR spectra. The compounds provide an excellent introduction into the effects that aromaticity and electron donating/withdrawing groups have on 1H NMR chemical shifts. The porphyrin ring systems' extensive electron "clouds" provide excellent examples of diamagnetic anisotropy due to the circulation of the electrons within their molecular orbitals. Furthermore, the 1H NMR spectra of the para-substituted compounds, H2[(p-X)4TPP], provide an excellent example of spin coupling systems (between the ortho and meta protons on the phenyl rings) with a range of Dv/J ratios.
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| More Information |
 Citation |
Falvo, RaeAnne E.; Mink, Larry M.; Marsh, Diane F. J. Chem. Educ. 1999 76 237.
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Keywords |
Instrumental Methods; Organic Chemistry; Microscale; NMR Spectrometry; Synthesis; Organic Synthesis
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History |
Created:
Last Updated: |
June 15, 1999
June 22, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1999
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February
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237
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