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Crystal structure and spectroscopic properties of 4-acetaminopyridine and its protonated form

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
4-Acetaminopyridine dihydrate and its protonated form, stabilized as the hydrochloride salt have been synthesized and spectroscopic elucidated in solution and in the solid-state by means of the inear-polarized solid state IR-spectroscopy (IR-LD), UV-spectroscopy, TGA, DSC, and the positive and negative ESI MS. Quantum chemical calculations were used to obtain the electronic structure, vibrational data and the electronic spectra. The spectroscopic and theoretical data are compared with the structure of the first compound obtained by single crystal X-ray diffraction. The effect of Npy protonation on the optical and magnetic properties of a 4-acetaminopyridine is discussed.
Rocznik
Strony
35--40
Opis fizyczny
Bibliogr. 27 poz., rys., tab.
Twórcy
autor
autor
autor
autor
  • Lehrstuhl für Analytische Chemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44780 Bochum, Germany, BKoleva@chem.uni-sofia.bg
Bibliografia
  • 1. Molgo, J., Lemeignan, M., Peradejordi, F. & Lechat, P. (1985). Presynaptic effects of aminopyridines on the neuromuscular junction of vertebrates J. Pharmacol. (Paris) 16, 109-121.
  • 2. Kirsch, G. E., Yeh, J. Z. & Oxford, G. S. (1986). Modulation of aminopyridine block of potassium currents in squid axon, Biophys. J. 50, 637-644.
  • 3. Molgo, J., Lemeignan, M., Lechat, P. & Peradejordi, F. (1985). Increase in evoked transmitter release from motor nerve terminals by some amino N-heterocyclic compounds I. Comparative experimental activities and extracellular pH-dependence, Eur. J. Med. Chem. 20, 149-153.
  • 4. Carlsson, C., Rosen, I. & Nilsson, E. (1993) Can 4-Aminopyridine be Used to Reverse Anaesthesia and Muscle Relaxation? Acta Anaesthesiol. Scand., 27, 87-90.
  • 5. Schwid, S., Petrie, M., McDermott, M., Tierney, D., Maso, D. & Goodman, A. (1997). Quantitative assessment of sustained-release 4-aminopyridine for symptomatic treatment of multiple sclerosis, Neurology 48, 817-821.
  • 6. McEvoy, K. M., Windebank, A. J., Daube, J. R. & Low, P. A., (1989). 3,4-Diaminopyridine in the treatment of Lambert-Eaton myasthenic syndrome. New Engl. J. Med. 321, 1567-1571.
  • 7. Segal, J. L. & Brunnemann, S. R. (1997). 4-Aminopyridine improves pulmonary function in quadriplegic humans with long-standing spinal cord injury. Pharmacotherapy 17, 415-423.
  • 8. Sellin, L. C. (1981). The action of botulinum toxin at the neuromuscular junction. Med. Biol. 59, 11-20.
  • 9. Davidson, M., Zemishlany, J. H. & Mohs, R. C. (1988). Alzheimer's Disease: A Report of Progress in Research. Biol. Psychiatry 23, 485-490.
  • 10. Meves, H. & Pichon, H. (1979). The effects of 4-aminopyridine on the potassium current in internally profused giant axons of the squid. J. Physiol. Lond. 251, 60-63.
  • 11. Raust, J., Goulay-Dufay, S., Le Hoang, M., Pradeau, D. & Guyon, F. (2007). Stability studies of ionised and nonionised 3,4-diaminopyridine: Hypothesis of degradation pathways and chemical structure of degradation products, J. Pharmaceut. Biomed. Anal. 43, 83-88.
  • 12. Ivanova, B. & Mayer-Figge, H. (2005). Crystal structure and Solid state IR-LD spectral analysis of new mononuclear Cu(II) complex with 4-aminopyridine. J. Coord. Chem. 58, 653-659.
  • 13. Ivanova, B., Arnaudov, M. & Mayer-Figge, H. Molecular spectral analysis and crystal structure of 4-aminopyridinium tetrachloropalladate(II) complex salt. (2005). Polyhedron 24(13), 1624-1630.
  • 14. Koleva, B., Trendafilova, E., Arnaudov, M., Sheldrick, W. S. & Mayer-Figge, H. (2006). Structural analysis of a mononuclear copper(II) complex of 3-aminopyridine. Trans. Met. Chem. 31, 866-873.
  • 15. Koleva, B. B., Kolev, T., Tsanev, T., Kotov, St., Mayer-Figge, H., Seidel, R. W. & Sheldrick, W. S. (2008). Spectroscopic and structural elucidation of 3,4-diaminopyridine and its hydrogentartarate salt. Crystal structure of 3,4-diaminopyridinium hydrogentartarate dehydrate. J. Mol. Struct. 881, 146-155.
  • 16. Koleva, B. B., Kolev, T., Tsanev, T., Kotov, St., Mayer-Figge, H., Seidel, R. S. & Sheldrick, W. S. (2008). 3,4-diaminopyridine bis(perchlorate): structural and spectroscopic elucidation? Struct. Chem. 19(1), 13-20.
  • 17. Koleva, B. B., Kolev, T., Seidel, R. W., Tsanev, T., Mayer-Figge, H., Spiteller, M. & Sheldrick, W. S. (2008). Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate. Spectrochim. Acta, Part A, 71,. 695-702.
  • 18. Emsley, J., Arif, M., Bates, P. & Hursthouse, M. (1988). Bis(acetato)bis[4-(N-acetylamino)pyridine]aquacopper(II)-hydrogen fluoride-hydrate (1/2/2): X-ray structure reveals H2O·HF hydrogen bonded in the lattice. J. Chem. Soc. Dalton. Trans. 1493-1497.
  • 19. Aakeroy, C. B., Hussain, I., Forbes, S. & Desper, J. (2007). Exploring the hydrogen-bond preference of N-H moieties in co-crystals assembled via O-H(acid) N(py) intermolecular interactions. Cryst. Eng. Comm. 9, 46-55.
  • 20. Sheldrick, G. M. 1995, SHELXTL, Release 5.03 for Siemens R3 crystallographic research system. Siemens Analytical X-Ray Instruments, Inc., Madison, USA.
  • 21. Sheldrick, G. M. 1997, SHELXS97 and SHELXL97. University of Göttingen, Germany.
  • 22. Ivanova, B. B., Arnaudov, M. G. & Bontchev, P. R. (2004). Linear-dichroic infrared spectral analysis of Cu(I)-homo-cysteine complex. Spectrochim Acta 60(4)A, 855-862.
  • 23. Ivanova, B. B.; Tsalev, D. L. & Arnaudov, M. G. (2006). Validation of reducing-difference procedure for the interpretation of non-polarized infrared spectra of n-component solid mixtures. Talanta 69, 822-828.
  • 24. Ivanova, B. B., Simeonov, V. D., Arnaudov, M. G. & Tsalev, D. L. (2007). Linear-dichroic infrared spectroscopy — validation and experimental design of the orientation technique as suspension in nematic liquid crystal. Spectrochim Acta 67A, 66-75.
  • 25. Koleva, B. B., Kolev, T., Simeonov, V., Spassov, T. & Spiteller, M. (2008). Linear polarized IR-spectroscopy of partial oriented solids as a colloid suspension in nematic liquid crystal — new tool for structural elucidation of the chemical compounds. J. Incl. Phen, 61, 319-333.
  • 26. Frisch, M. J., Trucks, G. W., Schlegel, HB., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, Jr. J. A., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, Ö., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Salvador, P., Dannenberg, J. J., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Baboul, A. G., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komáromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Andres, J. L., Gonzalez, C., Head-Gordon, M., Replogle, E. S. & Pople, J. A. Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.
  • 27. Zhurko, G. A. & Zhurko, D. A., ChemCraft: Tool for treatment of chemical data, Lite version build 08 2005.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BPS2-0053-0007
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