Premium
PHOTOCHEMICAL FORMATION OF NITROXIDE RADICALS FROM CARCINOGENIC N ‐METHYL‐ N '‐NITRO‐ N ‐NITROSOGUANIDINE AND RELATED COMPOUNDS
Author(s) -
Ioki Y.,
Imamura A.,
Nagata C.,
Nakadate M.
Publication year - 1975
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1975.tb06693.x
Subject(s) - nitroxide mediated radical polymerization , chemistry , nitroso compounds , nitroso , radical , photochemistry , nitro , electron paramagnetic resonance , carcinogen , methyl radical , nitro compound , alkyl , medicinal chemistry , organic chemistry , radical polymerization , nuclear magnetic resonance , physics , copolymer , polymer
— Potent carcinogenic N ‐methyl‐ N '‐nitro‐ N ‐nitrosoguanidine (MNNG) was found to be converted into a free radical by photoirradiation in organic solvents. The structure of the free radical produced was investigated by means of the electron paramagnetic resonance (EPR) method using isotope‐replaced compounds and also considering the results of the molecular orbital calculations. Upon illumination, release of the nitroso group and oxygen attack at the N ‐methyl nitrogen occurred, and the radical was identified as a nitroxide radical. Similar types of nitroxide radical were obtained from other N ‐alkyl‐ N ‐nitroso compounds, such as N ‐ethyl‐, N ‐propyl‐, and N ‐butyl‐ N '‐nitro‐ N ‐nitroso‐guanidine.