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Host: Guest chemistry of diaza-18-crown-6: Selective precipitation from mixtures of oligohydroxy phenols and the structures of five host: Guest complexes

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Abstract

Diaza-18-crown-6 (1,4,10,13-tetraoxa-7,16-diaza-cyclo-octadecane) selectively precipitates as a 1,4-dihydroxybenzene-complex from a mixture of isomeric phenols and as a 2,6-dihydroxynapthalene-complex from mixtures of isomeric diols. These selective precipitations are discussed in terms of structure and solubility of the host-guest complexes and phenol acidity. The crystal structures of diaza-18-crown-6 with guestsp-nitrophenol (2: 1), 2,4-dinitroaniline (2: 1), 5,5-diethylbarbituric acid (2: 1), salicylaldoxime (2: 1) and 1,4-dihydroxybut-2-yne (1: 1) are reported.

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Authors and Affiliations

  1. Department of Chemistry, Texas Christian University, 76129, Fort Worth, Texas, USA

    William H. Watson

  2. Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-5300, Bonn 1, Germany

    F. Vögtle & W. M. Müller

Authors
  1. William H. Watson
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  2. F. Vögtle
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  3. W. M. Müller
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Additional information

Supplementary Data relating to this article are deposited with the British Library as Supplementary Publication No. SUP 82065 (74 pages).

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Watson, W.H., Vögtle, F. & Müller, W.M. Host: Guest chemistry of diaza-18-crown-6: Selective precipitation from mixtures of oligohydroxy phenols and the structures of five host: Guest complexes. Journal of Inclusion Phenomena 6, 491–505 (1988). https://doi.org/10.1007/BF00660747

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  • DOI: https://doi.org/10.1007/BF00660747

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