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Updated: Apr 14, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Coextraction of water into nitrobenzene with organic ions
Yasuhiro Naito1, Wataru Murakami1, Kazuo Eda1
1†Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe 657-8501, Japan.
Abstract:
Various organic anions (sulfonates (RSO3(-)), carboxylates (RCO2(-)), and phenolates (RO(-))) and ammonium cations (RNH3(+), R2NH2(+), and R3NH(+)) were distributed in the nitrobenzene (NB)-water system by using Crystal Violet and dipicrylaminate, respectively. The number of water molecules (n) being coextracted into NB with an ion was then determined by the Karl Fischer method. The n values determined and those reported previously showed the variation from 0.51 to 3.4, depending on not only the charged groups but also the noncharged R-groups. In this study, we focused our attention to the strong electric field on the charged group and its facilitation effect for binding water molecules in NB. The local electric field (Ei) on the surface of an organic ion was evaluated by using Gaussian09 program with a subprogram developed in our recent study. It was found that the n values showed a clear dependence on the average value of Ei on oxygen or hydrogen atoms, respectively, of an anionic or cationic group.
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