Kinetics,mechanism, and products of the reaction of diphenylcarbonyl oxide with carboxylic acids |
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| Authors: | Nazarov A M Khursan S L Chainikova E M Komissarov V D |
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| Institution: | (1) Ufa Scientific Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation;(2) Bashkir State University, 32 ul. Frunze, 450074 Ufa, Russian Federation |
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| Abstract: | The kinetics of the reactions of acetic, benzoic, formic, oxalic, malic, tartaric, trifluoroacetic, and hydrochloric acids with diphenylcarbonyl oxide Ph2COO was studied. The carbonyl oxide Ph2COO was generated by flash photolysis of diphenyldiazomethane Ph2CN2 in solutions of acetonitrile and benzene at 295 K. The apparent rate constants of the reaction range from 4.6·108 for (COOH)2 in MeCN to 7.5·109 L mol–1 s–1 for acetic acid in a benzene solution. The reaction mechanism was proposed, according to which at the first stage the carbonyl oxide is reversibly solvated by the solvent. Then the solvated carbonyl oxide reacts with the acid molecule by the mechanism of insertion at the O—H bond. |
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| Keywords: | carbonyl oxides flash photolysis carboxylic acids kinetics of reactions |
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