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"As Simple as Possible, but Not Simpler"—The Case of Dehydroascorbic Acid
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Abstract
Ascorbic acid (vitamin C) is an essential nutrient, whose metabolic roles depend on its function as a reducing agent. Textbooks routinely assign its oxidized form, dehydroascorbic acid, a tricarbonyl structure that is highly improbable in aqueous solution and inconsistent with its colorless appearance. The actual structures of the various forms of dehydroascorbic acid have been known for at least a quarter of a century so that the continued use of the oversimplified tricarbonyl structure is hard to excuse. The experimental results on studies of oxidized forms of ascorbic acid are summarized here, and a plea is entered for accurate descriptions of chemical structures in this and other cases, even at the cost of some simplicity. A group exercise based on dehydroascorbic acid, which we have used in second-semester organic chemistry, is included in the online material.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
BiochemistryKeywords (Pedagogy):
Misconceptions / Discrepant EventsKeywords (Subject):
Bioorganic ChemistryCiting Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
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Jeffrey J. Warren and James M. MayerJournal of the American Chemical Society2010 132 (22), 7784-7793Tuning of the Thermochemical and Kinetic Properties of Ascorbate by Its Local Environment: Solution Chemistry and Biochemical Implications
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- Received: August 03, 2009
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