Abstract
Composition and structure of crystals of unknown origin, crystallizing spontaneously from ethylenediamine on standing, has been determined by elemental analysis, FTIR, 1H and 13C NMR spectroscopy and X-ray diffraction. The crystal with molecular formula C6H14N4 has been found to be a highly symmetric saturated imino compound with double-ring structure, and unambiguously identified as trans-1,4,5,8-tetraazodecalin by 1H NMR and powder X-ray diffraction based on both its specific AA'BB' spin coupling system and simulated XRD pattern calculated from available data of previous single crystal structure determination, respectively. Simultaneous TG/DTA measurement shows one-step degradation of this compound. The volatile decomposition products have been followed by both TG/DTA-MS and TG-FTIR. Group of the largest fragments (m/z=80, 81 and 82) observed by TG/DTA-MS corresponds to an aromatic 1,4-diazine (pyrazine). In the EGA-FTIR spectrum of released gaseous species measured at the highest evolution rate by TG-FTIR, ethylenediamine can be identified as another decomposition product.
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References
Medicines Commission, British Pharmacopoeia 1993, Vol. I., London: HMSO.
W. Martindale, The Extra Pharmacopoeia, 29 th Edition (1989) London, The Pharmaceutical Press.
J. Nishijo, K. Ohno and K. Nishimura, Chem. Pharm. Bull., 30 (1982) 2219.
M. F. Garbauskas, R. P. Goehner and A. M. Davis, Acta Crystallogr., C39 (1983) 1684.
M. C. Rezende, E. L. Dall'Oglio and C. Zucco, Tetrahedron Lett., 30 (1996) 5265.
M. C. Rezende, C. A. Marques, E. L. Dall'Oglio and C. Zucco, Liebigs Ann. Recl., 5 (1997) 925.
C. Castellani-Bisi, S. Facchetti, H. Knöppel and A. Copet, Chim. Ind. (Milan), 52 (1970) 1110.
H. Baganz, L. Domaschike and G. Kirchner, Chem. Ber., 94 (1961) 2676.
B. Fuchs and A. Ellencweig, Recl. Trav. Chim. Pays-Bas, 98 (1979) 326.
R. Müller, W. von Philipsborn, L. Schleifer, P. Aped and B. Fuchs, Tetrahedron, 6 (1991) 1013.
M. Ferrari, G. B. Giovenzana, G. Palmisano and M. Sisti, Synth. Commun., 30 (2000) 15.
M. Antoine, H. Bernard, N. Kervarec and H. Handel, J. Chem. Soc., Perkin Trans. 2., 3 (2002) 552.
W. May and H. G. von Schnering, Z. Naturforsch. B Anorg. Chem. Org. Chem., 33 (1978) 881.
P. Böttcher, H. Buchkremer-Hermanns, W. Hönle and H. G. von Schnering, Z. Kristallogr., 181 (1987) 223.
M. Bán, J. Madarász, G. Pokol and S. Gál, Solid State Ionics (2004) (In press, Ms. No.: SOSI 9434)
J. Madarász, P. Bombicz, K. Jármi, M. Bán, G. Pokol and S. Gál, J. Therm. Anal. Cal., 69 (2002) 281.
M. Bán, J. Madarász, P. Bombicz, G. Pokol and S. Gál, Thermochim. Acta, 420 (2004) 105.
Cambridge Structural Database (CSD), I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Perason and R. Taylor, Acta Crystallogr., B58 (2002) 389.
Beilstein Database of Organic Chemistry, Institute zur Förderung der Chemischer Wissenschaften, 2003 release.
NIST Chemistry WebBook, Standard Database No. 69, March, 2003 release, EPA Vapor Phase Library, http://webbook.nist.gov/chemistry.
Integrated Spectral Data Base System for Organic Compounds, March 2004 release, http://www.aist.go.jp/RIODB/SDBS/menu-e.html.
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Bán, M., Madarász, J., Bombicz, P. et al. TRANS-1,4,5,8-tetraazodecalin crystals occurring in ethylenediamine. Journal of Thermal Analysis and Calorimetry 78, 545–555 (2004). https://doi.org/10.1023/B:JTAN.0000046118.95640.d9
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DOI: https://doi.org/10.1023/B:JTAN.0000046118.95640.d9