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Molecular structures of 8,8′-dithioureido-2,2′-binaphthalene derivatives and their anions recognition: an ONIOM investigation

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Abstract

The structures of 8,8′-bis(3-phenylthioureidomethyl)-2,2′-binaphthalene (1), 8,8′-bis(3-butylthioureidomethyl)-2,2′-binaphthalene (2) and their complexes with anionic guests such as carboxylate ions (acetate, oxalate, malonate, succinate, glutarate, adipate, pimelate, suberate, and azelate), inorganic oxygen-containing anions (nitrate, sulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate), and halide ions (fluoride, chloride, and bromide) were obtained using the ONIOM approach. The binding abilities of receptors 1 and 2 to anionic species in terms of binding energy, thermodynamic properties, and selectivity coefficient were obtained at the ONIOM(B3LYP/6-31G(d):AM1) and BSSE-corrected B3LYP/6-31G(d)//ONIOM(B3LYP/6-31G(d):AM1) levels of theory. The multipoint hydrogen bonding between receptors (either the receptor 1 or 2) and anionic guests were found. The hydrogen phosphate is the most preferable ion to bind with either the receptor 1 or 2.

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Acknowledgment

The authors gratefully acknowledge the Thailand Research Fund for financial support (Grant no. BRG5180016).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Center for Petroleum, Petrochemicals and Advanced Materials, Chulalongkorn University, Bangkok, 10330, Thailand

    Sirichai Piyaauksornsak, Totsaporn Tangthongkul, Raina Wanbayor & Vithaya Ruangpornvisuti

  2. Department of Chemistry, Faculty of Science, Mahasarakham University, Mahasarakham, 44150, Thailand

    Banchob Wanno

Authors
  1. Sirichai Piyaauksornsak
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  2. Totsaporn Tangthongkul
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  3. Raina Wanbayor
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  4. Banchob Wanno
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  5. Vithaya Ruangpornvisuti
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Correspondence to Vithaya Ruangpornvisuti.

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Piyaauksornsak, S., Tangthongkul, T., Wanbayor, R. et al. Molecular structures of 8,8′-dithioureido-2,2′-binaphthalene derivatives and their anions recognition: an ONIOM investigation. Struct Chem 20, 767–780 (2009). https://doi.org/10.1007/s11224-009-9466-4

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  • DOI: https://doi.org/10.1007/s11224-009-9466-4

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