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

• Authors: Michail Arnaudov , Bojidarka Ivanova , Shishman Dinkov
• Languages of publication: EN

Abstracts

EN

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.

Keywords

EN

4-aminopyridine; difference IR spectral analysis

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2004
• Volume: 2
• Issue: 4
• Pages: 589-597

Dates

published

1 - 12 - 2004

online

1 - 12 - 2004

Contributors

author

Michail Arnaudov

• Department of Chemistry, University of Sofia, 1164, Sofia, Bulgaria

author

Bojidarka Ivanova

• Department of Chemistry, University of Sofia, 1164, Sofia, Bulgaria

author

Shishman Dinkov

• Department of Chemistry, University of Sofia, 1164, Sofia, Bulgaria

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. http://dx.doi.org/10.1016/S0006-3495(01)75750-5[Crossref]
• [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. http://dx.doi.org/10.1177/0091270003251388[Crossref]
• [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. http://dx.doi.org/10.1002/anie.198806921
• [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. http://dx.doi.org/10.1016/0022-2860(94)87039-X[Crossref]
• [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. [Crossref]
• [6] E. Spiner: “The vibrational spectra and structures of the hydrochlorides of aminopyridines”, j. Chem. Soc., (1962), pp. 3119–3125. [Crossref]
• [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. http://dx.doi.org/10.1071/CH9692595[Crossref]
• [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. http://dx.doi.org/10.1016/0022-2860(93)80195-2[Crossref]
• [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. http://dx.doi.org/10.1016/0022-2860(95)08561-9[Crossref]
• [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.
• [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. http://dx.doi.org/10.1016/S0022-2860(98)00584-5[Crossref]
• [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.
• [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. [Crossref]
• [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. [Crossref]
• [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. http://dx.doi.org/10.1016/0022-2852(61)90345-9[Crossref]
• [18] W.K. Thompson: “Infrared absorbtion spectra of Dimethyl sulphoxide solutions. Part I. Heterocyclic amines”, J. Chem. Soc., (1962), pp. 617–621. [Crossref]
• [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. http://dx.doi.org/10.1016/S0022-2860(98)00638-3[Crossref]
• [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. http://dx.doi.org/10.1016/S0022-2860(02)00674-9[Crossref]
• [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.
• [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.
• [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.
• [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.
• [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.
• [26] H. Wolff and D. Mathias: “Hydrogen bonding and Fermi-resonance of aniline”, J. Phys. Chem., Vol. 77, (1973), pp. 2081–2084. http://dx.doi.org/10.1021/j100636a010[Crossref]
• [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.
• [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. http://dx.doi.org/10.1107/S0567740877006487[Crossref]
• [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.
• [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. http://dx.doi.org/10.1016/S0022-2860(00)00740-7[Crossref]
• [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. http://dx.doi.org/10.1021/j100017a018[Crossref]
• [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.

Identifiers

DOI

10.2478/BF02482723