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On the protonated state of amidinium-like diaromatic derivatives: X-ray and UV studies

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Abstract

We present the crystal structures of the chloride salts of the mono-guanidinium 1 (–CH2CH2– linker) and the bis-isouronium 2 (–O– linker) that have been resolved by us indicating that these compounds are diprotonated in the solid state as informed by the counterions positions. To determine the pK a values of these compounds as well as those of their analogues 3 (mono-2-aminoimidazolinium with a –CH2CH2– linker) and 4 (mono-guanidinium with a –O– linker), the corresponding UV–Vis titrations were carried out. Thus, in aqueous solution compounds 1, 3 and 4 were present as mono-cationic species while derivative 2 was a bis-cation.

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Notes

  1. CCDC-contains the supplementary crystallographic data for this paper. CCDC depository numbers for compounds 1 and 2 are CCDC 733785 and CCDC 733784, respectively. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; email: deposit@ccdc.cam.ac.uk].

References

  1. Rodriguez F, Rozas I, Kaiser M, Brun R, Nguyen B, Wilson WD, Garcia RN, Dardonville C (2008) New bis(2–aminoimidazoline) and bis-guanidne DNA minor groove binders with potent in vivo antitrypanosomal and antiplasmodial activity. J Med Chem 51:909–923

    Article  CAS  Google Scholar 

  2. Nagle PS, Rodriguez F, Kahvedžić A, Quinn SJ, Rozas I (2009) Non-symmetrical diaromatic guanidinium/2-aminoimidazolinium derivatives: synthesis and DNA affinity. J Med Chem 52:7113–7121

    Article  CAS  Google Scholar 

  3. Nagle PS, Rodriguez F, Quinn SJ, O’Donovan DH, Kelly JM, Nguyen B, Wilson WD, Rozas I (2010) Biophysical studies on the DNA interaction with non-symmetrical guanidinium/2-aminoimidazolinium derivatives. Org Biomol Chem 8:5558–5567

    Article  CAS  Google Scholar 

  4. Rodriguez F, Rozas I, Ortega JE, Meana JJ, Callado LF (2007) Guanidine and 2-aminoimidazoline aromatic derivatives as α2-adrenoceptor antagonists, 1: towards new antidepressants with heteroatomic linkers. J Med Chem 50:4516–4527

    Article  CAS  Google Scholar 

  5. Rodriguez F, Rozas I, Ortega JE, Erdozain AM, Meana JJ, Callado LF (2008) Guanidine and 2-aminoimidazoline aromatic derivatives as α2-adrenoceptor antagonists, 2: exploring aliphatic linkers. J Med Chem 51:3304–3312

    Article  CAS  Google Scholar 

  6. Rodriguez F, Rozas I, Ortega JE, Erdozain AM, Meana JJ, Callado LF (2009) Guanidine and 2-aminoimidazoline aromatic derivatives as α2-adrenoceptor ligands: searching for structure-activity relationships. J Med Chem 52:601–609

    Article  CAS  Google Scholar 

  7. Kinsella GK, Watson GW, Rozas I (2006) Theoretical proton affinities of α1 adrenoceptor ligands. Bioorg Med Chem 14:1580–1587

    Article  CAS  Google Scholar 

  8. Kinsella GK, Rodriguez F, Watson GW, Rozas I (2007) Computational approach to the basicity of a series of α1 adrenoceptor ligands in aqueous solution. Bioorg Med Chem 15:2850–2855

    Article  CAS  Google Scholar 

  9. Goonan A, Kahvedžić A, Rodriguez F, Nagle P, McCabe T, Rozas I, Erdozain AM, Meana JJ, Callado LF (2008) Novel synthesis and pharmacological evaluation as α2-adrenoceptor ligands of O-phenylisouronium salts. Bioorg Med Chem 16:8210–8217

    Article  CAS  Google Scholar 

  10. Dardonville C, Goya P, Rozas I, Alsasua A, Martin I, Borrego MJ (2000) New aromatic iminoimidazolidine derivatives as alpha1-adrenoceptor antagonists: a novel synthetic approach and pharmacological activity. Bioorg Med Chem 8:1567–1577

    Article  CAS  Google Scholar 

  11. Software Reference Manual, version 5.625; Bruker Analytical X-Ray Systems Inc.: Madison, WI, 2001. Sheldrick, G. M. SHELXTL, An Integrated System for Data Collection, Processing, Structure Solution and Refinement; Bruker Analytical X-Ray Systems Inc.: Madison, WI, 2001

  12. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) Mercury CSD 2.4-new features for the visualization and investigation of crystal structures. J Appl Cryst 41:466–470

    Article  CAS  Google Scholar 

  13. Brown CJ (1949) The crystal structure of aniline hydrochloride. Acta Crystallogr 2:228–232

    Article  CAS  Google Scholar 

  14. Cambridge Structural Database (CSD) search

  15. Haas DJ, Harris DR, Mills HH (1965) The crystal structure of guanidinium chloride. Acta Crystallogr 19:676–679

    Article  CAS  Google Scholar 

  16. Palm VA (ed) (1975–1979) Tables of rate and equilibrium constants of heterolytic organic reactions, VINITI, volume II-1. Guanidines. Tartu University Publishing House, Jakobi, pp 326–328

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Acknowledgements

This research was funded by the SFI-RFP project CHE275.

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  1. School of Chemistry, Trinity College, University of Dublin, Dublin 2, Ireland

    Padraic S. Nagle, Amila Kahvedžić, Thomas McCabe & Isabel Rozas

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  1. Padraic S. Nagle
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  2. Amila Kahvedžić
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  3. Thomas McCabe
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  4. Isabel Rozas
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Correspondence to Isabel Rozas.

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Nagle, P.S., Kahvedžić, A., McCabe, T. et al. On the protonated state of amidinium-like diaromatic derivatives: X-ray and UV studies. Struct Chem 23, 315–323 (2012). https://doi.org/10.1007/s11224-011-9861-5

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  • DOI: https://doi.org/10.1007/s11224-011-9861-5

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