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2001
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June
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In the Laboratory
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Isolation and Spectral Analysis of Naturally Occurring Thiarubrine A
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Juan Reyes and Melita Morton
Department of Chemistry, Florida International University, Miami, FL 33199
Kelsey Downum
Department of Biology, Florida International University, Miami, FL 33199
Gary G. Hoffman and Kevin E. O'Shea
Department of Chemistry, Florida International University, Miami, FL 33199
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June 2001
Vol. 78 No. 6
p. 781
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| Abstract |
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We have designed an experiment in which students isolate and characterize thiarubrine A, a pseudo-antiaromatic 1,2-dithia-3,5-cyclohexadiene derivative. Thiarubrines are an important class of compounds which have recently received attention because of their unusual reactivity, unique biological activity, and potential medicinal applications. They possess a distinctive red color and structure features that are particularly useful for demonstrating UV-vis, NMR, and IR spectral analyses. A crude mixture containing thiarubrine A is obtained by methanol (liquid-solid) extraction of the roots of short ragweed, Ambrosia artemisiifolia. Alternatively, these compounds can be isolated from numerous taxa within the family Asteraceae. Thiarubrine A possesses alkyl, alkenyl, and alkynyl functionality, which is useful in illustrating the utility of IR and NMR in the characterization of natural products. The long wavelength UV-vis absorption band of thiarubrine is indication of the nonplanarity of dithiin ring and provides an excellent opportunity to discuss the concepts of aromaticity, conjugation, and molecular orbital theory.
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| Supplement |
A drawing and detailed description for the identification of short ragweed, a summary of the molecular modeling studies, the 13C NMR spectra, and the IR spectrum are available.
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 Contents |
JCE2001p0781W.doc (Microsoft Word)
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| Download |
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| More Information |
Citation |
Reyes, Juan; Morton, Melita; Downum, Kelsey; O'Shea, Kevin E. J. Chem. Educ. 2001 78 781.
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Keywords |
Aromaticity / Aromatics; IR Spectroscopy; Laboratory Instruction; Natural Products; NMR Spectrometry; Organic Chemistry; UV-Vis Spectroscopy
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History |
Created:
Last Updated: |
May 8, 2001
August 31, 2005
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