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tautomer

tautomer (tôˈtəmər) [key], one of two or more structural isomers that exist in equilibrium and are readily converted from one isomeric form to another. Of the various types of tautomerism that are possible, two are commonly observed. In keto-enol tautomerism a simultaneous shift of electrons and a hydrogen atom occurs; it was first observed by K. Meyer in the ethyl ester of 3-oxobutanoic acid (ethyl acetoacetate), which occurs naturally as a mixture of the two forms. Ring-chain tautomerism, first recognized by Emil Fischer, is exhibited by glucose. It arises as a result of the aldehyde group (CHO) in a sugar chain molecule reacting with one of the hydroxy groups (OH) in the same molecule to give it a cyclic (ring-shaped) form.

The Columbia Electronic Encyclopedia, 6th ed. Copyright © 2012, Columbia University Press. All rights reserved.

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