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A facile synthesis of amide-based receptors under microwave conditions: investigation of their anion recognition properties by experimental and computational tools

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Abstract

Two novel amide-based receptors were synthesized under microwave irradiation. Their chemical structures were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. The binding properties of these amide-based receptors to various anions (H2PO4 −, HSO4 −, C6H5CO2 −, CH3CO2 −, ClO4 −, F−, Cl−, and Br−) were examined by UV titration in THF at 20 °C. The results indicated that the receptors form 1:1 complexes with anions and they have the strongest affinity for fluoride (F−) among the anions considered. Molecular dynamics calculations by AMBER and quantum mechanical calculations performed at the B3LYP and M062X levels of theory using the 6-31 + g(d,p) basis set provided models for the complexation mode between the receptors and anions and yielded binding energies for the complexes.

The computed interaction mode of tripodals (1a and 1b) with fluoride.

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Acknowledgements

We are grateful for the financial support from The Scientific and Technological Research Council of Turkey (TUBITAK) with project no. 109 T787 and from Dicle University Research Council (DÜBAP) with project 09-FF-67.

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Authors and Affiliations

  1. Faculty of Science, Department of Chemistry, Dicle University, 21280, Diyarbakir, Turkey

    Gülşen Öztürk, Salih Subari, Sevil Şeker, Mahmut Toğrul, Şafak Özhan Kocakay & Necmettin Pirinççioğlu

  2. Health School, Department of Nursing, Batman University, 72100, Batman, Turkey

    Selami Ercan

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  1. Gülşen Öztürk
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  2. Salih Subari
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  3. Sevil Şeker
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Correspondence to Gülşen Öztürk or Necmettin Pirinççioğlu.

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Öztürk, G., Subari, S., Şeker, S. et al. A facile synthesis of amide-based receptors under microwave conditions: investigation of their anion recognition properties by experimental and computational tools. J Mol Model 23, 249 (2017). https://doi.org/10.1007/s00894-017-3390-0

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