The structure of 2,4,6-tris[di(tert-butoxycarbonyl)methylidene]-hexahydro-1,3,5-triazine |
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| Authors: | A V Shastin T I Godovikova T S Pivina N I Golovina G V Shilov Yu A Strelenko B L Korsunskii V P Lodygina |
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| Institution: | (1) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow Region, Russian Federation;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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| Abstract: | The structure of 2,4,6-trisdi(tert-butoxycarbonyl)methylidene]hexahydro-1,3,5-triazine was studied by quantum chemistry, NMR and IR spectroscopy, and X-ray
diffraction. This compound exists exclusively in the hexahydro-1,3,5-triazine form both in solution and in the solid phase,
although due to the loss of the aromatization energy, this structure should be less stable than a 1,3,5-triazine structure.
The formation of strong intramolecular hydrogen bonds confirmed by NMR and IR spectroscopy and X-ray diffraction data may
be a main reason for stabilization of the hexahydro-1,3,5-triazine isomer.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1022–1026, June, 2006. |
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| Keywords: | prototropic tautomerism 2 4 6-tris[di(tert-butoxycarbonyl)methylidene]hexahydro-1 3 5-triazine structure 1H and 15N NMR spectra X-ray diffraction semiempirical quantum chemical calculations |
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