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tautomerism

Isomerism of the general form:
T06252-1
where the isomers (called tautomers) are readily interconvertible; the atoms connecting the groups X, Y, Z are typically any of C, H, O or S, and G is a group which becomes an electrofuge or nucleofuge during isomerization. The commonest case, when the electrofuge is H+, is also known as 'prototropy'. Examples, written so as to illustrate the general pattern given above, include: Keto-enol tautomerism, such as:
T06252-2
T06252-3
The grouping Y may itself be a three-atom (or five-atom) chain extending the conjugation, as in:
T06252-4
The double bond between Y and Z may be replaced by a ring, when the phenomenon is called ring-chain tautomerism, as in:
T06252-5
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1171
InChI=1/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)/f/h7H
GCNTZFIIOFTKIY-QDQILVOLCT
InChI=1/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)/f/h6H
GCNTZFIIOFTKIY-BRMMOCHJCN
InChI=1/C8H12O5/c1-4-5(9)13-8(12,6(10)11)7(4,2)3/h4,12H,1-3H3,(H,10,11)/f/h10H
XCVUQMYEBSBXPN-KZFATGLACO
InChI=1/C8H12O5/c1-4(6(10)11)8(2,3)5(9)7(12)13/h4H,1-3H3,(H,10,11)(H,12,13)/f/h10,12H
QOGCXTXBWCCNTB-QIQUEDJNCN
InChI=1/C9H14O4/c1-5-6(10)13-9(4,7(11)12)8(5,2)3/h5H,1-4H3,(H,11,12)/f/h11H
AUFHUNBTRGWGCF-WXRBYKJCCI
InChI=1/C6H10O3/c1-3-9-6(8)4-5(2)7/h4,7H,3H2,1-2H3/b5-4+
ROBJRQHNPKJRFH-SNAWJCMRBC
InChI=1/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
XYIBRDXRRQCHLP-UHFFFAOYAP
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.T06252.
Original PDF version: http://www.iupac.org/goldbook/T06252.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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