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Effect of anions on supramolecular architecture of benzimidazole-based ionic salts

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Abstract

The reaction of N,N,N′,N′-tetrakis-(1H,benzimidazol-2ylmethyl) propane-1,3-diamine (L) with different inorganic acids affords salts viz., LH4 4+·4ClO4 −·H2O (1), LH4 4+·4Cl−·2H2O (2), LH4 4+·2H2PO4 −·H7P3O12 2−·3H3PO4 (3), LH4 4+·4NO3 − (4), and 2LH+·2CF3COO−·5H2O (5). The X-ray crystallographic studies revealed that the proton transfer occurred from acid to the ligand. It also demonstrated that different type of hydrogen bond between protonated ligand and anions is responsible for the supramolecular framework. The colorimetric test showed color change upon the addition of acids in the solution of the ligand. The photo-physical experiments suggested the fluorescence properties of ligand in the presence of acids.

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References

  1. Steed JW (2006) Chem Commun 2637–2649

  2. Martínez-Máñez R, Sancenón F (2003) Chem Rev 103:4419–4476

    Article  CAS  Google Scholar 

  3. Caltagirone C, Gale PA (2009) Chem Soc Rev 38:520–538

    Article  CAS  Google Scholar 

  4. Gale PA, García-Garrido SE, Garric J (2008) Chem Soc Rev 37:151–190

    Article  CAS  Google Scholar 

  5. Sessler JL, Barkey NM, Pantos GD, Lynch VM (2007) New J Chem 31:646–654

    Article  CAS  Google Scholar 

  6. Rurack K, Resch-Genger U (2002) Chem Soc Rev 31:116–127

    Article  CAS  Google Scholar 

  7. Tajc SG, Miller BL (2006) J Am Chem Soc 128:2532–2533

    Article  CAS  Google Scholar 

  8. Nofal ZM, Soliman EA, Abd El-Karim SS, El Zahar Ml, Srour AM, Sethumadhavan S, Maher TJ (2011) Acta Pol Pharm 68:519–534

    CAS  Google Scholar 

  9. Tonelli M, Simone M, Tasso B, Novelli F, Boido V, Sparatore F, Paglietti G, Prid S, Gilliberti G, Blois S, Ibba C, Sanna G, Loddo R, La Colla P (2010) Biorg Med Chem 18:2937–2953

    Article  CAS  Google Scholar 

  10. Rathee PS, Dhankar R, Bhardwaj S, Gupta M, Kumar R (2011) J Appl Pharma Sci 4:127–130

    Google Scholar 

  11. Chen G, Liu Z, Zhang Y, Shan X, Jhang L, Zhao Y, He W, Feng Z, Yang S, Liang G (2013) Med Chem Lett 4:64–74

    Google Scholar 

  12. Coon T, Moore WJ, Li B, Yu J, Zarkani-Kord S, Malanv S, Santos MA, Hernandez LM, Petroshi KE, Sun A, Wen J, Sullivan S, Haelewyn J, Hedrick M, Hoare SJ, Bradbury MJ, Crowe PD, Beaton G (2009) Bioorg Med Chem Lett 19:4380–4384

    Article  CAS  Google Scholar 

  13. Arunachalam M, Chakraborty S, Marivel S, Ghosh P (2012) Cryst Growth Des 12:2097–2108

    Article  CAS  Google Scholar 

  14. Gogoi A, Das G (2012) Cryst Growth Des 12:4012–4021

    Article  CAS  Google Scholar 

  15. Singh N, Jang DO (2007) Org Lett 9:1991–1994

    Article  CAS  Google Scholar 

  16. Lee DY, Singh N, Kim MJ, Jang DO (2011) Org Lett 13:3024–3027

    Article  CAS  Google Scholar 

  17. Joo TY, Singh N, Lee GW, Janga DO (2007) Tetrahedron Lett 48:8846–8850

    Article  CAS  Google Scholar 

  18. Yu M, Lin H, Zhao G, Lin H (2007) J Mol Recognit 20:69–73

    Article  CAS  Google Scholar 

  19. Ghosh K, Kar D (2007) Beilstein J Org Chem 7:254–264

    Article  CAS  Google Scholar 

  20. Molina P, Tárraga A, Otón F (2012) Org Biomol Chem 10:1711–1724

    Article  CAS  Google Scholar 

  21. Hiscock JR, Gale PA, Lalaoui N, Lighta ME, Wells NJ (2012) Org Biomol Chem 10:7780–7788

    Article  CAS  Google Scholar 

  22. Yoon J, Kim SK, Singh NJ, Kim KS (2006) Chem Soc Rev 35:355–360

    Article  CAS  Google Scholar 

  23. Ji BM, Deng DS, Ma N, Miao SB, Yang XG, Ji LG, Du M (2010) Cryst Growth Des 10:3060–3069

    Article  CAS  Google Scholar 

  24. Perrin DD, Armarego WL, Perrin DR (1980) Purification of laboratory chemicals, 2nd edn. Pergamon, New York

    Google Scholar 

  25. Oki AR, Bommarreddy PR, Zhang H, Hosmane N (1995) Inorg Chim Acta 231:109–114

    Article  CAS  Google Scholar 

  26. Sheldrick GM (1996) SADABS. University of Göttingen, Göttingen

    Google Scholar 

  27. Sheldrick GM (1990) Acta Cryst A 46:467–473

    Article  Google Scholar 

  28. Sheldrick GM (2000) SHELXTL-NT version 6.12, reference manual. University of Göttingen, Göttingen

    Google Scholar 

  29. Brandenburg K (2000) Diamond: Visual Crystal Structure Information System (Version 2.1d). Crystal Impact GbR, Bonn

    Google Scholar 

  30. Mercury, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, United Kingdom. Available from: http://www.ccdc.cam.ac.uk/

  31. Kang SO, Llinares JM, Powell D, VanderVelde D, Bowman-James K (2003) J Am Chem Soc 125:10152–10153

    Article  CAS  Google Scholar 

  32. Ilioudis CA, Tocher DA, Steed JW (2004) J Am Chem Soc 126:12395–12402

    Article  CAS  Google Scholar 

  33. Lakshminarayanan PS, Kumar DK, Ghosh P (2005) Inorg Chem 44:7540–7546

    Article  CAS  Google Scholar 

  34. Chmielewski MJ, Charon M, Jurczak J (2004) Org Lett 6:3501–3504

    Article  CAS  Google Scholar 

  35. Lakshminarayanan PS, Ravikumar I, Suresh E, Ghosh P (2007). Chem Commun 5214–5216

  36. Etter MC (1990) Acc Chem Res 23:120–126

    Article  CAS  Google Scholar 

  37. Amendola V, Boiocchi M, Esteban-Gomez D, Fabbrizzi L, Monzani E (2005) Org Biomol Chem 3:2632–2639

    Article  CAS  Google Scholar 

  38. Sessler JL, Cho DG, Lynch V (2006) J Am Chem Soc 128:16518–16519

    Article  CAS  Google Scholar 

  39. Ju J, Park M, Suk J-M, Lah M-S, Jeong K-S (2008). Chem Commun 3546–3548

  40. Singh UP, Kashyap S, Singh HJ, Butcher RJ (2011) CrystEngComm 13:4110–4120

    Article  CAS  Google Scholar 

  41. Wu B, Huang X, Xia Y, Yang X-J, Janiak C (2007) CrystEngComm 9:676–685

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge UGC and CSIR, New Delhi, India, for financial assistance in form of SRF to RRM and RA to SK.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247 667, India

    Udai P. Singh, Radha Raman Maurya & Sujata Kashyap

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  1. Udai P. Singh
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  2. Radha Raman Maurya
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  3. Sujata Kashyap
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Correspondence to Udai P. Singh.

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Singh, U.P., Maurya, R.R. & Kashyap, S. Effect of anions on supramolecular architecture of benzimidazole-based ionic salts. Struct Chem 25, 733–743 (2014). https://doi.org/10.1007/s11224-013-0317-y

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  • DOI: https://doi.org/10.1007/s11224-013-0317-y

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