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Bambus[6]uril as a novel example of a ditopic ion-pair molecular receptor for sodium iodide

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Abstract

By using quantum mechanical DFT calculations, the most probable structure of the bambus[6]uril-Na+I− electroneutral complex species was derived. In this complex with a plane of symmetry, the considered anion I−, included in the macrocyclic cavity, is bound by 12 weak hydrogen bonds between methine hydrogen atoms on the convex face of glycoluril units and the I− anion, while the sodium cation Na+ interacts only with two carbonyl oxygen atoms of the parent macrocyclic receptor. The interaction energy of the resulting complex, involving the Boys-Bernardi counterpoise corrections of the basis set superposition error, was found to be −593.8 kJ mol−1.

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References

  1. Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L (2005) Angew Chem Int Ed 44:4844

    Article  CAS  Google Scholar 

  2. Lee JW, Samal S, Selvapalam N, Kim HJ, Kim K (2003) Acc Chem Res 36:621

    Article  CAS  Google Scholar 

  3. Liu S, Ruspic C, Mukhopadhyay P, Chakrabarti S, Zavalij PY, Isaacs L (2005) J Am Chem Soc 127:15959

    Article  CAS  Google Scholar 

  4. Freeman WA, Mock WL, Shih NY (1981) J Am Chem Soc 103:7367

    Article  CAS  Google Scholar 

  5. Mock WL, Shih NY (1983) J Org Chem 48:3618

    Article  CAS  Google Scholar 

  6. Mock WL, Shih NY (1986) J Org Chem 51:4440

    Article  CAS  Google Scholar 

  7. Mock WL, Shih NY (1988) J Am Chem Soc 110:4706

    Article  CAS  Google Scholar 

  8. Mock WL, Shih NY (1989) J Am Chem Soc 111:2697

    Article  CAS  Google Scholar 

  9. Isobe H, Tomita N, Lee JW, Kim HJ, Kim K, Nakamura E (2000) Angew Chem Int Ed 39:4257

    Article  CAS  Google Scholar 

  10. Isobe H, Sota S, Lee JW, Kim HJ, Kim K, Nakamura E (2005) Chem Commun 1549

  11. Tan Y, Choi S, Lee JW, Ko YH, Kim K (2002) Macromolecules 35:7161

    Article  CAS  Google Scholar 

  12. Márquez C, Hudgins RR, Nau WM (2004) J Am Chem Soc 126:5806

    Article  CAS  Google Scholar 

  13. Buschmann HJ, Mutihac L, Mutihac RC, Schollmeyer E (2005) Thermochim Acta 430:79

    Article  CAS  Google Scholar 

  14. Buschmann HJ, Schollmeyer E, Mutihac L (2003) Thermochim Acta 399:203

    Article  CAS  Google Scholar 

  15. Svec J, Necas M, Sindelar V (2010) Angew Chem Int Ed 49:2378

    Article  CAS  Google Scholar 

  16. Toman P, Makrlík E, Vaňura P (2011) Monatsh Chem 142:881

    Article  CAS  Google Scholar 

  17. Toman P, Makrlík E, Vaňura P (2011) Comput Theor Chem 989:97

    Article  CAS  Google Scholar 

  18. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  19. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision C.02, Gaussian Inc, Wallingford

    Google Scholar 

  21. Kříž J, Dybal J, Makrlík E (2006) Biopolymers 82:536

    Article  CAS  Google Scholar 

  22. Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2008) Supramol Chem 20:487

    Article  CAS  Google Scholar 

  23. Kříž J, Dybal J, Makrlík E, Budka J (2008) J Phys Chem A 112:10236

    Article  CAS  Google Scholar 

  24. Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2009) J Phys Chem A 113:5896

    Article  CAS  Google Scholar 

  25. Kříž J, Toman P, Makrlík E, Budka J, Shukla R, Rathore R (2010) J Phys Chem A 114:5327

    Google Scholar 

  26. Kříž J, Dybal J, Makrlík E, Vaňura P, Moyer BA (2011) J Phys Chem B 115:7578

    Article  CAS  Google Scholar 

  27. Toman P, Makrlík E, Vaňura P (2011) Acta Chim Slov 58:846

    CAS  Google Scholar 

  28. Makrlík E, Toman P, Vaňura P (2012) Monatsh Chem 143:199

    Article  CAS  Google Scholar 

  29. Makrlík E, Toman P, Vaňura P (2013) Monatsh Chem 144:919

    Article  CAS  Google Scholar 

  30. Boys SF, Bernardi F (1970) Mol Phys 19:553

    Article  CAS  Google Scholar 

  31. van Duijneveldt FB, van Duijneveldt-van de Rijdt JGCM, van Lenthe JH (1994) Chem Rev 94:1873

  32. Hobza P, Šponer J (1999) Chem Rev 99:3247

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No.: 42900/1312/3114 “Environmental Aspects of Sustainable Development of Society”, by the Czech Ministry of Education, Youth, and Sports (Project MSM 6046137307), and by the Czech Science Foundation (Project P 205/10/2280).

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Authors and Affiliations

  1. Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Czech Republic

    Emanuel Makrlík

  2. Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    Petr Toman

  3. Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Czech Republic

    Petr Vaňura

Authors
  1. Emanuel Makrlík
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  2. Petr Toman
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  3. Petr Vaňura
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Correspondence to Emanuel Makrlík.

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Makrlík, E., Toman, P. & Vaňura, P. Bambus[6]uril as a novel example of a ditopic ion-pair molecular receptor for sodium iodide. Monatsh Chem 145, 721–724 (2014). https://doi.org/10.1007/s00706-014-1154-4

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  • DOI: https://doi.org/10.1007/s00706-014-1154-4

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