The intramolecular hydrogen migration which can be observed in enzymatic and chemical hydroxylations of aromatic rings. It is evidenced by appropriate deuterium labelling, i.e.
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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 (https://doi.org/10.1351/pac199466051077)