THE CHEMILUMINESCENCE OF INDOLE DERIVATIVES IN DIMETHYL SULFOXIDE* |
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| Authors: | A W BERGER † J N DRISCOLL † J S DRISCOLL J A PIROG § H LINSCHITZ| |
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| Institution: | Boston Laboratory, Monsanto Research Corporation, Everett, Massachusetts and Department of Chemistry, Brandeis University, Waltham, Massachusetts 02154, U.S.A.;|Department of Chemistry, Brandeis University, Waltham, Massachusetts. |
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| Abstract: | The chemiluminescent autoxidation of over fifty indoles has been measured in dimethyl sulfoxide (DMSO). The 3-alkylindole derivatives represent the brightest and most efficient members of this group. The chemiluminescence yield (per mole) of skatole is (1·5 ± 0·6) × 10-3. The chemiluminescence spectrum of skatole is identical with the fluorescence spectrum of o-formamidoacetophenone in the same environment Similar results for 2,3-dimethylindole lead to the identification of the acylamide anion as the emitter in indole chemiluminescence. A peroxide ring cleavage excitation mechanism is proposed. |
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