Aromatic nucleophilic substitution. XV. Stopped-flow kinetics of the formation and decomposition of 1,3- and 1,1-disubstituted Meisenheimer complexes in the reactions of 1-dialkylamino-2,4-dinitronaphthalenes with potassium methoxide in dimethyl sulfoxide

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概要

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• The formation of 1,3-disubstituted anionic σ complexes, followed by 1,1-disubstituted ones was confirmed by means of absorption and NMR spectra in the reactions of 1-dialkylamino-2,4-dinitronaphthalenes with potassium methoxide in DMSO-CH<SUB>3</SUB>OH. The rates and activation parameters were determined by kinetic studies with use of stopped-flow and conventional spectrophotometers. The rate constants for the formation of 1,3-disubstituted one decreased in the order 1-dimethylamino->1-(<I>N</I>-methylbutyl)amino->1-piperidino->1-diethylamino-2,4-dinitronaphthalenes, those for its decomposition being comparable with each other. On the other hand, the rate constant for the formation of 1,1-disubstituted one decreased in the same order as above while that for its decomposition decreased in the order 1-dimethylamino->1-(<I>N</I>-methylbutyl)amino->1-diethylamino->1-piperidino-2,4-dinitronaphthalenes. The mechanism was discussed from activation parameters.

• 公益社団法人 日本化学会の論文

著者

• Sekiguchi Shizen

  Department of Chemistry, Faculty of Engineering, Gunma University

• Matsui Kohji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Tomoto Noboru

  Faculty of Engineering, Miyazaki University

• Takei Toshio

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

• Takei Toshio

  Department of Synthetic Chemistry, Gunma University

• Tone Noboru

  Department of Synthetic Chemistry, Gunma University

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