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NIH shift

The intramolecular hydrogen migration which can be observed in enzymatic and chemical hydroxylations of aromatic rings. It is evidenced by appropriate deuteriumlabelling, i.e.
N04142
In enzymatic reactions the NIH shift is generally thought to derive from the rearrangement of arene oxide intermediates, but other pathways have been suggested. (NIH stands for U.S. National Institutes of Health where the shift was discovered.)
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1145
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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. https://doi.org/10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: https://doi.org/10.1351/goldbook.N04142.
Original PDF version: http://www.iupac.org/goldbook/N04142.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 The PDF version is out of date and is provided for reference purposes only.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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