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Crystal associates of 18-crown-6 and polyfluoro(het)arylenediamines: structure, properties, and selectivity of formation

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Abstract

The new group of objects in crystal engineering, namely, 1 : 1 associates of polyfluoro(het)arylenediamines and 18-crown-6, being supramolecular 1D assemblies, is considered. Diamine isomerism is shown to serve as a design tool for control of the supramolecular architecture, and the nature of the aromatic framework and location and volume of substituents determine linear dimensions of the elementary unit in an assembly. A linear dependence of the enthalpy of melting of co-crystals on the length of the assembly unit is observed in the series of the meta-(het)arylenediamine and 18-crown-6 associates. The effect of selective co-crystallization of polyfluoroarylenediamines with crown ether is used in practice for the isolation of high-purity compounds from mixtures of products of the non-selective amination of basic polyfluoroarenes.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent´eva, 630090, Novosibirsk, Russian Federation

    T. A. Vaganova, Yu. V. Gatilov & E. V. Malykhin

  2. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    Yu. V. Gatilov

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  1. T. A. Vaganova
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  2. Yu. V. Gatilov
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  3. E. V. Malykhin
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Correspondence to T. A. Vaganova.

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Based on the materials of the V International Conference on Physical Chemistry of Crown Compounds, Porphyrins, and Phthalocyanines (September 15—19, 2014, Tuapse).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1746—1756, August, 2015.

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Vaganova, T.A., Gatilov, Y.V. & Malykhin, E.V. Crystal associates of 18-crown-6 and polyfluoro(het)arylenediamines: structure, properties, and selectivity of formation. Russ Chem Bull 64, 1746–1756 (2015). https://doi.org/10.1007/s11172-015-1069-1

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  • DOI: https://doi.org/10.1007/s11172-015-1069-1

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