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Conformational and configurational diversity of solvent inclusion complexes of some calix[4]pyrroles and their anion recognition properties

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Abstract

Sterically hindered meso-tetramethyl-meso-tetraarylcalix[4]pyrroles 1-4 where aryl is p-fluorophenyl 1, p-chlorophenyl 2, and p-methylphenyl 3, 4 (configurational isomers) are synthesized and purified by the recrystallization technique. They are characterized by IR, 1H and 13C NMR, and mass spectroscopy. Configurational isomers ααββ (3) and αααα (4) of meso-tetramethyl-meso-tetramethylphenylcalix[ 4]pyrroles are assigned by the 1H NMR studies and confirmed by the X-ray diffraction analysis. The single crystal X-ray diffraction analysis reveals that the ethanol adduct of 1, the acetone adduct of 2 and 3 adopt the 1,2-conformation while the acetone-water adduct of 1 and the acetone adduct of 4 adopt partial cone and cone conformations respectively. The conformational diversity is due to non-covalent interactions among the encapsulated guest, pyrrolic NH protons, and meso- substituents. Anion binding studies (F–, Cl–, CH3COO–, HSO −4 ) are carried out through 1H NMR titrations; the binding constants are evaluated using the EQNMR program, displaying that they are more selective towards fluoride rather than other anions with the 1:1 stoichiometry. The configuration of compounds drastically influences the ion-recognition processes.

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Authors and Affiliations

  1. Department of Chemistry, Hans Raj Mahila Maha Vidyalaya, Jalandhar, Punjab, India

    A. Sharma

  2. Department of Chemistry, Dr. B. R. Ambedkar National Institute of Technology, Jalandhar, Punjab, India

    S. Obrai

  3. Department of Chemistry, Lyallpur Khalsa College of Engineering, Jalandhar, Punjab, India

    R. Kumar

  4. Department of Chemistry, Guru Nanak Dev University, Amritsar, Punjab, India

    A. Kaur & M. S. Hundal

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  1. A. Sharma
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Correspondence to A. Sharma.

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Original Russian Text © 2015 A. Sharma, S. Obrai, R. Kumar, A. Kaur, M. S. Hundal.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1439-1448, November-December, 2015.

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Sharma, A., Obrai, S., Kumar, R. et al. Conformational and configurational diversity of solvent inclusion complexes of some calix[4]pyrroles and their anion recognition properties. J Struct Chem 56, 1379–1389 (2015). https://doi.org/10.1134/S0022476615070203

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