https://doi.org/10.1351/goldbook.N04142
The
In enzymatic reactions the NIH shift is generally thought to derive from 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. ![Not defined](/img/inline/N04142.png)
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.)