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Infrared study of the proton acceptor ability of metyrapone
Author(s) -
Migchels P.,
ZeegersHuyskens Th.
Publication year - 1995
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610080204
Subject(s) - chemistry , pyridine , adduct , hydrogen bond , protonation , infrared spectroscopy , photochemistry , hydrogen , steric effects , acceptor , carbon tetrachloride , ring (chemistry) , medicinal chemistry , proton , oxide , hydrogen atom , organic chemistry , molecule , group (periodic table) , ion , physics , quantum mechanics , condensed matter physics
The hydrogen bond complexes between metyrapone [methyl‐1,2‐di(3‐pyridyl)propan‐1‐one] and hydroxylic proton donors (phenols, water) were investigated by infrared spectroscopy. The thermodynamic and spectroscopic data determined in carbon tetrachloride suggest that the nitrogen atom of the pyridine ring A [bonded to the C(CH 3 ) 2 group] is the main hydrogen bond interaction site. The data are compared with di‐2‐pyridylglyoxal complexes where the hydrogen bonds are formed on the oxygen atom of the carbonyl function. In the solid adduct of metyrapone with HCl, protonation takes place on the two nitrogen atoms of the pyridine rings. The data from this work are compared with those from chemical oxidation, which leads predominantly to the formation of mono‐ N ‐oxide A and di‐ N ‐oxide.