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Photoreactions of p ‐Quinones with Dimethyl Sulfide and Dimethyl Sulfoxide in Aqueous Acetonitrile †
Author(s) -
Görner Helmut
Publication year - 2006
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 - 10.1562/2005-05-25-ra-540
Subject(s) - chemistry , dimethyl sulfoxide , dimethyl sulfide , semiquinone , quinone , acetonitrile , photochemistry , chloranil , juglone , reaction rate constant , redox , benzoquinone , hydroquinone , anthraquinone , aqueous solution , electron transfer , medicinal chemistry , sulfur , inorganic chemistry , organic chemistry , kinetics , physics , quantum mechanics
The effects of dimethyl sulfide (DMS) and dimethyl sulfoxide (DMSO) on the photoreactions of 1,4‐benzoquinone (BQ), 1,4‐naphthoquinone (NQ), 9,10‐anthraquinone (AQ) and several derivatives in acetonitrile/water were studied. The observed triplet state of the quinones is quenched and the rate constant is close to the diffusion‐controlled limit for reactions of most quinones with DMS and lower with DMSO. Semiquinone radical anions (Q *‐ ) produced by electron transfer from sulfur to the triplet quinone were detected. For both DMS and DMSO the yield of Q *‐ is similar, being generally low for BQ and NQ, substantial for AQ and largest for chloranil. The specific quencher concentrations and the effects of quinone structure and redox potentials on the time‐resolved photochemical properties are discussed.