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CHEMILUMINESCENCE FROM THE OXIDATION OF AUXIN DERIVATIVES
Author(s) -
Durán Nelson,
Zinner Klaus,
Baptista Roberto Casadei de,
Vidigal Carmen C. C.,
Cilento Giuseppe
Publication year - 1976
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.1751-1097.1976.tb06841.x
Subject(s) - chemistry , dioxetane , indole test , acetonitrile , aldehyde , photochemistry , chemiluminescence , indole 3 acetic acid , acetic anhydride , acetic acid , organic chemistry , auxin , catalysis , biochemistry , gene
— The thiophenyl ester of indole‐3‐acetic acid and indole‐3‐acetonitrile produce chemiluminescence in aerated dimethylsulfoxide in the presence of potassium t ‐butoxide. The emitter is the aromatic aldehyde. In the case of acetonitrile, the other product expected from the cleavage of an intermediate dioxetane, cyanate/isocyanate, has also been identified. Other auxins also chemiluminesce under similar conditions, but the emitters have not been properly identified. These systems are models for the peroxidase catalyzed oxidation of indole‐3‐acetic acid to indole‐3‐carboxaldehyde and as such support the earlier inference (Vidigal et al , 1975) that the excited aldehyde is generated in the enzymic process. An additional result is the observation of an exciplex between excited indole‐3‐carboxaldehyde and the thiophenylester of indole‐3‐acetic acid. This appears to be the first case of chemical generation of an exciplex by a route other than radical ion reaction, presumably by the dioxetane route.