The 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO) was used
as a probe to study the changes in hydrogen bonding between the pheno
lic OH group and the ON group of the radical by means of NMR and EPR.
C-13 NMR contact shifts induced by TEMPO were measured for five phenol
s. Formation of intermolecular hydrogen bond between a phenol and TEMP
O molecule causes noticeable increase of N-14 hyperfine coupling const
ant in the radical and appearance of negative spin density on carbon n
uclei of C-OH fragment in the phenol.