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GIAO-DFT-NMR characterization of fullerene-cucurbituril complex: the effects of the C60@CB[9] host-guest mutual interactions

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Abstract

Magnetic shielding constants for an isolated fullerene C60, cucurbituril CB[9], and the host-guest complex C60@CB[9] were calculated as a function of separation of the monomers. Our results in the gas phase and water indicate a significant variation of the magnetic properties for all atoms of the monomers in the complex and after liberation of fullerene C60 from the interior of the CB[9] cavity. The interaction between the two monomers results in a charge transfer that collaborates with a redistribution of electron density to deshield the monomers.

NMR spectroscopy alteration on C60@CB[9] host-guest mutual interactionsᅟ

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References

  1. Zalesskiy SS, Danieli E, Blumich B, Ananikov VP (2014) Miniaturization of NMR systems: desktop spectrometers, microcoil spectroscopy, and “NMR on a Chip” for chemistry, biochemistry, and industry. Chem Rev 114:5641–5694

    Article  CAS  PubMed  Google Scholar 

  2. Toukach FV, Ananikov VP (2013) Recent advances in computational predictions of NMR parameters for the structure elucidation of carbohydrates: methods and limitations. Chem Soc Rev 42:8376–8415

    Article  CAS  PubMed  Google Scholar 

  3. Gancheff JS, Denis PA (2015) Relative affinity of bambus[6]uril towards halide ions: a DFT/GIAO approach in the gas phase, and in the presence of the solvent employing discrete and discrete-continuum models. Comput Theor Chem 1064:35–44

    Article  CAS  Google Scholar 

  4. Colherinhas G, Fonseca TL, Georg HC, Castro MA (2011) Isomerization effects on chemical shifts and spin-spin coupling constants of polyacetylene chains: a GIAO-DFT study. Int J Quantum Chem 111:1616–1625

    Article  CAS  Google Scholar 

  5. Colherinhas G, Fonseca TL, Castro MA (2011) 13C chemical shifts of polyacetylene chains with charged conformational defects: a GIAO–DFT study. Chem Phys Lett 503:191–196

    Article  CAS  Google Scholar 

  6. Simoes SM, Rey-Rico A, Concheiro A, Alvarez-Lorenzo C (2015) Supramolecular cyclodextrin-based drug nanocarriers. Chem Commun (Camb) 51:6275–6289

    Article  CAS  Google Scholar 

  7. Kang Y, Guo K, Li BJ, Zhang S (2014) Nanoassemblies driven by cyclodextrin-based inclusion complexation. Chem Commun (Camb) 50:11083–11092

    Article  CAS  Google Scholar 

  8. Nimse SB, Kim T (2013) Biological applications of functionalized calixarenes. Chem Soc Rev 42:366–386

    Article  CAS  PubMed  Google Scholar 

  9. Zadmard R, Alavijeh NS (2014) Protein surface recognition by calixarenes. RSC Adv 4:41529–41542

    Article  CAS  Google Scholar 

  10. Assaf KI, Nau WM (2015) Cucurbiturils: from synthesis to high-affinity binding and catalysis. Chem Soc Rev 44:394–418

    Article  CAS  PubMed  Google Scholar 

  11. Masson E, Ling X, Joseph R, Kyeremeh-Mensah L, Lu X (2012) Cucurbituril chemistry: a tale of supramolecular success. RSC Adv 2:1213–1247

    Article  CAS  Google Scholar 

  12. Zhao W, Wang C, Zhang Y, Xue S, Zhu Q, Tao Z (2015) Supramolecular assembly of a methyl-substituted cucurbit[6]uril and its potential applications in selective sorptio. New J Chem 39:2433–2436

    Article  CAS  Google Scholar 

  13. Kubota R, Hamachi I (2015) Protein recognition using synthetic small-molecular binders toward optical protein sensing in vitro and in live cells. Chem Soc Rev 44:4454–4471

    Article  CAS  PubMed  Google Scholar 

  14. Ghale G, Nau WM (2014) Dynamically analyte-responsive macrocyclic host–fluorophore systems. Acc Chem Res 47:2150–2159

    Article  CAS  PubMed  Google Scholar 

  15. Yang H, Yuan B, Zhang X, Scherman OA (2014) Supramolecular chemistry at interfaces: host-guest interactions for fabricating multifunctional biointerfaces. Acc Chem Res 47:2106–2015

    Article  CAS  PubMed  Google Scholar 

  16. Pinjari RV, Gejji SP (2008) Electronic structure, molecular electrostatic potential, and NMR chemical shifts in cucurbit[n]urils (n = 5-8), ferrocene, and their complexes. J Phys Chem A 112:12679–12686

    Article  CAS  PubMed  Google Scholar 

  17. Gobre VV, Pinjari RV, Gejji SP (2010) Density functional investigations on the charge distribution, vibrational spectra, and NMR chemical shifts in cucurbit[n]uril (n = 5-12) hosts. J Phys Chem A 114:4464–4470

    Article  CAS  PubMed  Google Scholar 

  18. Barooah N, Sundararajan M, Mohanty J, Bhasikuttan AC (2014) Synergistic effect of intramolecular charge transfer toward supramolecular pKa shift in cucurbit[7]uril encapsulated coumarin dyes. J Phys Chem B 118:7136–7146

    Article  CAS  PubMed  Google Scholar 

  19. Fileti E, Colherinhas G, Malaspina T (2014) Predicting the properties of a new class of host–guest complexes: C60 fullerene and CB[9] cucurbituril. Phys Chem Chem Phys 16:22823–22829

    Article  CAS  PubMed  Google Scholar 

  20. Buschmann HJ, Zielesny A (2013) Geometric, electronic and NMR properties of hemicucurbit[n]urils and their anionic complexes. Comput Theor Chem 1022:14–22

    Article  CAS  Google Scholar 

  21. Buschmann HJ, Wego A, Zielesny A, Schollmeyer E (2006) Structure, electronic properties and NMR-shielding of cucurbit[n]urils. J Incl Phenom Macrocycl Chem 54:85–88

    Article  CAS  Google Scholar 

  22. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  23. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785

    Article  CAS  Google Scholar 

  24. Ditchfield R (1974) Self-consistent perturbation theory of diamagnetism. Mol Phys 27:789–807

    Article  CAS  Google Scholar 

  25. Wolinski K, Hinton JF, Pulay P (1990) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc 112:8251–8260

    Article  CAS  Google Scholar 

  26. Pascual-Borras M, Lopez X, Poblet JM (2015) Accurate calculation of (31)P NMR chemical shifts in polyoxometalates. Phys Chem Chem Phys 17:8723–8731

    Article  CAS  PubMed  Google Scholar 

  27. Gerber IC, Jolibois F (2015) Theoretical gas to liquid shift of (15)N isotropic nuclear magnetic shielding in nitromethane using ab initio molecular dynamics and GIAO/GIPAW calculations. Phys Chem Chem Phys 17:12222–12227

    Article  CAS  PubMed  Google Scholar 

  28. Vahakangas J, Ikalainen S, Lantto P, Vaara J (2013) Nuclear magnetic resonance predictions for graphenes: concentric finite models and extrapolation to large systems. Phys Chem Chem Phys 15:4634–4641

    Article  CAS  PubMed  Google Scholar 

  29. Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3094

    Article  CAS  PubMed  Google Scholar 

  30. Miertuš S, Scrocco E, Tomasi J (1981) Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects. Chem Phys 55:117–129

    Article  Google Scholar 

  31. Frisch MJ et al (2009) Gaussian 09. Gaussian, Inc., Wallingford

    Google Scholar 

  32. Mulder FA, Filatov M (2010) NMR chemical shift data and ab initio shielding calculations: emerging tools for protein structure determination. Chem Soc Rev 39:578–590

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

This work was supported by grants from Brazilian agencies FAPEG, FAPESP, and CNPq.

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Authors and Affiliations

  1. Departamento de Física - CEPAE and Instituto de Física, Universidade Federal de Goiás, Goiânia, GO, 74690-900, Brazil

    Guilherme Colherinhas

  2. Instituto de Ciência e Tecnologia, Universidade Federal de São Paulo, São José dos Campos, SP, 12231-280, Brazil

    Eudes Eterno Fileti & Thaciana Malaspina

Authors
  1. Guilherme Colherinhas
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  2. Eudes Eterno Fileti
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  3. Thaciana Malaspina
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Correspondence to Guilherme Colherinhas.

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Colherinhas, G., Fileti, E.E. & Malaspina, T. GIAO-DFT-NMR characterization of fullerene-cucurbituril complex: the effects of the C60@CB[9] host-guest mutual interactions. J Mol Model 24, 181 (2018). https://doi.org/10.1007/s00894-018-3719-3

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  • DOI: https://doi.org/10.1007/s00894-018-3719-3

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