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A reducing-difference IR-spectral study of 4-aminopyridine

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Central European Journal of Chemistry

Abstract

The IR-spectra of 4-aminopyridine (4-AP) in solution and in the solid state have been analyzed, using the reducing-difference procedure. Defining a more precise band assignment of a part of the characteristic frequencies of 4-AP, the data obtained proved in particular a Fermi-resonance splitting of the symmetric NH2-stretch.

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References

  1. A. Loboda and C.M. Armstrong: “Resolving the Gating Charge Movement Associated with Late Transitions in K Channel Activation”, Biophys. Journal, Vol. 81, (2001), pp. 905–916.

    Article  CAS  Google Scholar 

  2. C. Hayes, K.C. Katz, M.A. Devane, J.G. Hsieh, J.T.C., Wolfe, D.L. Potter and P.J.A.R. Blight: “Pharmacokinetics of an Immediate-Release Oral Formulation of Fampridine (4-Aminopyridine) in normal Subjects and Patients with Spinal Cord Injury”, J. Clin. Pharmacol., Vol. 43, (2003), pp. 379–385.

    Article  CAS  Google Scholar 

  3. R. Ballardini, M.T. Gandolfi, V. Balzani, F.H. Kohnke and J.F. Stoddart: “Second-Sphere Photochemistry and Photophysics: Luminescence of the [Pt(bpy)(NH3)2]2 -Dibenzo[30]crown-10 Adduct”, Angew. Chem., Int. Ed. Engl., Vol. 27, (1988), pp. 692–701.

    Article  Google Scholar 

  4. Z. Dega-Szafran, A. Kania, B. Nowak-Widra and M. Szafran: “UV, 1H and 13C NMR spectra, and AM1 studies of protonation of aminopyridines”, J. Mol. Struct., Vol. 322, (1994), pp. 223–232.

    Article  CAS  Google Scholar 

  5. T.J. Prior and M.J. Rosseinsky: “Crystal engineering of a 3-D coordination polymer from 2-D building blocks”, Chem. Commun., (2001), pp. 495–497.

  6. E. Spiner: “The vibrational spectra and structures of the hydrochlorides of aminopyridines”, j. Chem. Soc., (1962), pp. 3119–3125.

  7. B.D. Batts and E. Spiner: “Vibration spectral and structural comparison of the 4-aminopuridine cation with the 4-hydroxypiridinium N- and C-deuterated, and N-methylated ions. Relevant NMR. spectral studies”, Aust. J. Chem., Vol. 22, (1969), pp. 2595–2610.

    Article  CAS  Google Scholar 

  8. M.G. Arnaudov, B.B. Ivanova and Sh. Dinkov: “A linear dichroic infrared (IRLD) solid state spectral study of 4-aminopyridine”, Vibrational Spectroscopy, (2004), submitted.

  9. B. Jordanov, R. Nentchovska and B. Schrader: “FT-IR linear dichroic solute spectra of nematic solutions as a tool for IR band assignment”, J. Mol. Struct., Vol. 297, (1993), pp. 401–406.

    Article  CAS  Google Scholar 

  10. B. Jordanov and B. Schrader: “Reduced IR-LD spectra of substances oriented as nematic solutions”, J. Mol. Struct., Vol. 347, (1995), pp. 389–398.

    Article  CAS  Google Scholar 

  11. M.G. Arnaudov: “The influence of the medium on the infrared spectrum of self-associated systems”, Intern. J. Vibr. Spectrosc., Vol. 5, (2001), pp. 1–18.

    Google Scholar 

  12. M.G. Arnaudov and Sh. Dinkov: “IR-LD-spectral study on the self-association effects of 2-aminopyridine”, J. Mol. Struct., Vol. 476, (1999), pp. 235–241.

    Article  CAS  Google Scholar 

  13. M.G. Arnaudov and Y. Dimitriev: “Study on the structural transition in binary tellurite glasses by means of reduced infrared spectra”, Phys. Chem. Glasses, Vol. 42, (2001), pp. 99–102.

    CAS  Google Scholar 

  14. C.L. Angyal and R.L. Werner: “The tautomerism of N-heteroaromatic Amines. Part II. Infrared spectroscopic evidence”, J. Chem. Soc., (1952), pp. 2911–2915.

  15. J.D.S. Goulden: “The structure of the aminopyridines”, J. Chem. Soc., (1952), pp. 2939–2940.

  16. S.F. Maeson: “The frequencies and intensities of the NH stretching vibrations in primary amines”, J. Chem. Soc., (1958), pp. 3619–2627.

  17. K.V. Ramiah and P.G. Puranik: “Infrared Spectroscopic Studies of Association of amino-pyridines”, J. Mol. Spectrosc., Vol. 7, (1961), pp. 89–104.

    Article  CAS  Google Scholar 

  18. W.K. Thompson: “Infrared absorbtion spectra of Dimethyl sulphoxide solutions. Part I. Heterocyclic amines”, J. Chem. Soc., (1962), pp. 617–621.

  19. S. Akyuz: “The FT-IR spectroscopic investigation of transition metal(II) 4-aminopyridine tetracyanonickelate complexes”, J. Mol. Struct., Vol. 482, (1999), pp. 171–174.

    Article  Google Scholar 

  20. Y. Buyukmurat and S. Akyuz: “Theoretical and experimental studies of IR spectra of 4-aminopyridine metal(II) complexes”, J. Mol. Struct., Vol. 651, (2003), pp. 533–539.

    Article  CAS  Google Scholar 

  21. H. Wolff and D. Staschewski: “Raman spectroskopishe Utersuchungen die fluessingen primaeren aliphatishen Aminen. 2. Mitteilung. Eingehendere Deutung der an den NH-Valenzbanden gewonnen Ergebnisse”, Ber. Bunsenges. Phys. Chem., Vol. 66, (1962), pp. 140–155.

    CAS  Google Scholar 

  22. J. Lauransan, P. Pineau and M.-T. Josier: “Etude par spectroscopie infrarouge des association moleculaires entre la parabromoaniline et divers solvents”, Ann. Chim., Vol. 9, (1964), pp. 213–227.

    CAS  Google Scholar 

  23. J. Lauransan, J. Corset and M.-T. Forel: “Application du calcul de vibration a l'etude par spectrometrie infrarouge des complexes formee par liason hydrogene entre les groupements XH2 on XH3 et divers acceptenrs de proton”, Ann. Chim., Vol. 3, (1968), pp. 109–119.

    Google Scholar 

  24. H. Wolff and D. Horn: “Ueber die Fermi-Resonanz bei der Wasserstoffbrueckenassonziation primaerer aliphatisher Amine”, Ber. Bunsenges. Phys. Chem., Vol. 72, (1968), pp. 419–429.

    CAS  Google Scholar 

  25. H. Wolff and D. Horn: “Ultrarotspektroskopishe Untersuchungen der Wasserstoffbrueckenassoziation von 2,2,2-Trifluoraethylamin. 1. Mitteilung. Die Messesgebnisse und ihre elementare Deutung”, Ber. Bunsenges. Phys. Chem., Vol. 71, (1967), pp. 467–478.

    CAS  Google Scholar 

  26. H. Wolff and D. Mathias: “Hydrogen bonding and Fermi-resonance of aniline”, J. Phys. Chem., Vol. 77, (1973), pp. 2081–2084.

    Article  CAS  Google Scholar 

  27. M.G. Arnaudov and Sh. Dinkov: “IR-spectral study of self-association effects of 2-aminopyridine in solution”, Spectroscopy Letters., Vol. 31, (1998), pp. 1687–1703.

    CAS  Google Scholar 

  28. M. Chao and E. Schempp: “An X-ray and NQR study of 4-aminopyridine and related aromatic amines”, Acta. Crystall., Vol. B33, (1977), pp. 1557–1564.

    Article  Google Scholar 

  29. H. Wolff and J. Eints: “Ultrarotutersuchungen der Assoziation von primaeren mit tertiaeren aliphatishen Amines”, Ber. Bunsenges. Phys. Chem., Vol. 70, (1966), pp. 728–733.

    CAS  Google Scholar 

  30. V.E. Borisenko, A.V. Moreva, I. Faizullina and A. Koll: “Dynamic, electrooptical and energetic nonequivalency of NH bonds in 1∶1 and 1∶2 complexes of aminopyridines with proton acceptors”, J. Mol. Struct. Vol. 560, (2001), pp. 121–136.

    Article  CAS  Google Scholar 

  31. J. Smets, L. Adomowicz and G. Maes: “Matrix-Isolation FT-IR Studies and Ab-Initio Calculations of Hydrogen-Bonded Complexes of Molecules Modeling Cytosine or Isocytosine Tautomers. 2. 4-Aminopyridine and 4-Aminopyrimidine Complexes with H2O in Ar Matrixes”, J. Phys. Chem., Vol. 99, (1995), pp. 6387–6400.

    Article  CAS  Google Scholar 

  32. G. Keresztury, F. Billes, M. Kubinyi and T. Sundius: “A Density Functional, Infrared Linear Dichroism, and Normal Coordinate Study of Phenol and its Deuterated Derivatives: Revised Interpretation of the Vibrational Spectra”, J. Phys. Chem., Vol. 102A, (1998), pp. 1371–1380.

    Google Scholar 

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Arnaudov, M.G., Ivanova, B.B. & Dinkov, S.G. A reducing-difference IR-spectral study of 4-aminopyridine. cent.eur.j.chem. 2, 589–597 (2004). https://doi.org/10.2478/BF02482723

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  • DOI: https://doi.org/10.2478/BF02482723

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