Journal of Chemical Sciences

, Volume 129, Issue 5, pp 579–587 | Cite as

Inclusion complexation of tetrabutylammonium iodide by cyclodextrins

  • Biswajit Datta
  • Aditi Roy
  • Mahendra Nath Roy
Regular Article


Host-guest inclusion complex of an ionic solid (tetrabutyl ammonium iodide) with \(\upalpha \)- and \(\upbeta \)-cyclodextrin has been explored by various physicochemical and spectroscopic methods. Surface tension and conductivity studies indicated 1:1 stoichiometry of the inclusion complexes and \(^{1}\hbox {H}\) NMR and FT-IR studies substantiated the inclusion phenomenon. Density, viscosity and refractive index studies characterized the interactions of cyclodextrin with tetrabutyl ammonium iodide, which also indicated greater extent of encapsulation in \(\upbeta \)-cyclodextrin than in \(\upalpha \)-cyclodextrin. Hydrophobic effect, structural effect, electrostatic force and H-bonding interactions were mainly exploited to explicate the formation of inclusion complex.

Graphical Abstract.

Synopsis: This work shows the construction of host-guest inclusion complex of an ionic solid, tetrabutyl ammonium iodide, into the hydrophobic cavity of \(\alpha \)- and \(\beta \)-cyclodextrin. This study is based on the physicochemical parameters as well as spectroscopic data, which ascertain the efficiency of inclusion among ionic solid-cyclodextrin systems.


\(\upalpha \)- and \(\upbeta \)-Cyclodextrins ionic solid inclusion complex 



The authors are immensely grateful to SAP, Department of Chemistry, NBU under University Grants Commission (UGC), New Delhi. M. N. R. is obliged to University Grants Commission, New Delhi, Government of India for the award of one time grant under Basic Scientific Research for his dynamic service in the sophisticated research work.

Supplementary material

12039_2017_1267_MOESM1_ESM.docx (87 kb)
Supplementary material 1 (docx 87 KB)


  1. 1.
    Szejtli J 1998 Introduction and General Overview of Cyclodextrin Chemistry Chem. Rev. 98 1743CrossRefGoogle Scholar
  2. 2.
    Connors K A 1997 The Stability of Cyclodextrin Complexes in Solution Chem. Rev. 97 1325Google Scholar
  3. 3.
    Pinho E, Grootveld M, Soarse G and Henriques M 2014 Cyclodextrins as Encapsulation Agents for Plant Bioactive Compounds Carbohydr. Polym. 101 121Google Scholar
  4. 4.
    Wei B 2015 Corrigendum to “\(\upbeta \)-Cyclodextrin associated polymeric systems: Rheology, flow behavior in porous media and enhanced heavy oil recovery performance Carbohydr. Polym. 134 398Google Scholar
  5. 5.
    Yu, G, Hua B and Han C 2014 Proton Transfer in Host–Guest Complexation between a Difunctional Pillar[5]arene and Alkyldiamines Org. Lett. 16 2486Google Scholar
  6. 6.
    Li H, Chen D, Sun Y, Zheng, Y B, Tan L, Weiss P S and Yang Y 2013 Cyclodextrin-Modified Gold Nanospheres. Host-Guest Interactions at Work to Control Colloidal Properties J. Am. Chem. Soc. 135 1570CrossRefGoogle Scholar
  7. 7.
    Welton T 1999 Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 99 2071CrossRefGoogle Scholar
  8. 8.
    Winter B, Weber R, Schmidt P M and Hertel I V 2004 Photoemission from Aqueous Alkali-Metal-Iodide Salt Solutions Using EUV Synchrotron Radiation J. Phys. Chem. B  108 14558CrossRefGoogle Scholar
  9. 9.
    Bergersen H, Marinho R R T, Pokapanich W, Lindblad A, Björneholm O, Sæthre L J and Öhrwall J G 2007 The Surface Behavior of Hydrated Guanidinium and Ammonium Ions: A Comparative Study by Photoelectron Spectroscopy and Molecular Dynamics Phys.: Condens. Matter 19 326101Google Scholar
  10. 10.
    Li X, Xu X and Zhou C 2012 Visible-light induced oxidant-free oxidative cross-coupling for constructing allylic sulfones from olefins and sulfinic acids Chem. Commun. 48 12240Google Scholar
  11. 11.
    Liu Z J, Zhang J, Chen S L, Shi E, Xu Y and Wan X B 2012 Cross coupling of acyl and aminyl radicals: Direct synthesis of amides catalyzed by \(\text{ Bu }_{4}\text{ NI }\) with TBHP as an oxidant Angew. Chem. Int. Ed51 3231CrossRefGoogle Scholar
  12. 12.
    Uyanik M, Okamoto F, Yasui T and Ishihara K 2010 Quaternary ammonium (hypo)iodite catalysis for enantioselective oxidative cycloetherification Science 328 1376CrossRefGoogle Scholar
  13. 13.
    Sindelar V, Cejas M A, Raymo F M, Chen W, Parker S E and Kaifer A E 2005 Supramolecular assembly of 2,7-dimethyldiazapyrenium and cucurbit[8]uril: A new fluorescent host for detection of catechol and dopamine Chem. Eur. J. 11 7054CrossRefGoogle Scholar
  14. 14.
    Wang T, Wang M D, Ding C and Fu J 2014 Mono-benzimidazole functionalized \(\beta \)-coumaric acid Chem. Commun. 50 12469Google Scholar
  15. 15.
    Roy M N, Ekka D, Saha S and Roy M C 2014 Host–guest inclusion complexes of \(\upalpha \) -amino acids RSC Adv. 4 42383CrossRefGoogle Scholar
  16. 16.
    Roy M N, Roy A and Saha S 2016 Probing inclusion complexes of cyclodextrins with amino acids by physicochemical approach Carbohydr. Polym. 151 458Google Scholar
  17. 17.
    Saha S, Ray T, Basak S and Roy M N 2016 surface tension and conductivity studies to determine the inclusion mechanism: thermodynamics of host–guest inclusion complexes of natural amino acids in aqueous cyclodextrins New J. Chem. 40 651Google Scholar
  18. 18.
    Gao Y A, Li Z H, Du J M, Hou W G, Shen D, Zheng L Q and Zhang G Y 2005 Preparation and characterization of inclusion complexes of \(\upbeta \)-cyclodextrin with ionic liquid Chem. Eur. J.  11 5875CrossRefGoogle Scholar
  19. 19.
    Piñeiro Á, Banquy X, Pérez-Casas S, Tovar E, García A, Villa A, Amigo A, Mark A E and Costas M 2007 On the Characterization of Host-Guest Complexes: Surface Tension Calorimetry and Molecular Dynamics of Cyclodextrins with a Non-Ionic Surfactant J. Phys. Chem. B 111 4383CrossRefGoogle Scholar
  20. 20.
    Gao Y, Zhao X, Dong B, Zheng L, Li N and Zhang S 2006 Inclusion complexes of \(\upbeta \)-cyclodextrin with ionic liquid surfactants J. Phys. Chem. B 110 8576CrossRefGoogle Scholar
  21. 21.
    Roy M N, Saha S, Barman S and Ekka D 2016 Host–guest inclusion complexes of RNA nucleosides inside aqueous cyclodextrins explored by physicochemical and spectroscopic methods RSC Adv. 6 8881Google Scholar
  22. 22.
    Apelblat A, Manzurola E and Orekhova Z 2007 Electrical Conductance Studies in Aqueous Solutions with Glutamic Ions J. Solut. Chem. 36 891CrossRefGoogle Scholar
  23. 23.
    Ekka D and Roy M N 2014 RSC Adv. 4 19831Google Scholar
  24. 24.
    Masson D O 1929 Solute Molecular Volumes in Relation to The Solvation and Ionization Phil. Mag. 8 218CrossRefGoogle Scholar
  25. 25.
    Roy A, Saha S and Roy M N 2016 Study to explore host-guest inclusion complexes of cyclodextrins with biologically active molecules in aqueous environment Fluid Phase Equilib. 425 252Google Scholar
  26. 26.
    Jones G and Dole D 1929 The viscosity of aqueous solutions of strong electrolytes with special reference to barium chloride J. Am. Chem. Soc. 51 2950CrossRefGoogle Scholar
  27. 27.
    Negi J S and Singh S 2013 Spectroscopic investigation on the inclusion complex formation between amisulpride and \(\upgamma \)-cyclodextrin Carbohydr. Polym.  92 1835Google Scholar
  28. 28.
    Zhang W, Gong X, Cai Y, Zhang C, Yu X, Fan J and Diao G 2013 Investigation of water-soluble inclusion complex of hypericin with \(\upbeta \)-cyclodextrin polymer Carbohydr. Polym.  95 366Google Scholar
  29. 29.
    Milovanovic S, Markovic D, Aksentijevic K, Stojanovic D B, Ivanovic J and Zizovic I 2016 Application of cellulose acetate for controlled release of thymol Carbohydr. Polym.  147 344Google Scholar
  30. 30.
    Shamsipur M and Khayatian G 2001 Conductance Study of the Thermodynamics of Tl+ ion Complexes with Different 18-Membered Crown Ethers in Binary Dimethyl formamide-Acetonitrile Mixtures J. Inclusion Phenom. 39 109CrossRefGoogle Scholar
  31. 31.
    Barman S and Roy M N 2016 Hollow circular compound-based inclusion complexes of an ionic liquid RSC Adv. 6 76381CrossRefGoogle Scholar
  32. 32.
    Shoemaker D P and Garland C W 1967 In Experiments in Physical Chemistry (New York: McGraw-Hill) p.131Google Scholar

Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of North BengalDarjeelingIndia

Personalised recommendations