Flavin-related compounds: 3-Ethyl-lumiflavin. Combined DFT, NMR, X-ray and EI mass spectral study

E. Sikorska, J. Hernando, J. L. Bourdelande, I. Khmelinskii, M. Kubicki, A. Komasa, D. Prukała, M. Sikorski

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Abstract

3-Ethyl-lumiflavin was characterized by a variety of methods. Laser flash photolysis measurements in methanol solutions yielded a triplet state living 9.5 μs and a radical species living 91 μs, with steady-state photolysis quantum yields below 10-5. Fluorescence lifetime of 4.5 ns and quantum yield of 0.16 was recorded in aqueous solutions. Crystal structure determined by X-ray diffraction was quite similar to the geometry of an isolated molecule calculated using the DFT approach, with the observed differences attributable to a nonlinear hydrogen bond existing in the crystal solid. EI mass spectra revealed a fragmentation path specific to this compound and inexistent in lumiflavin or other similar compounds, due to ejection of a C 2H5-N=C=O molecule, containing the ethyl substituent of the parent molecule.
Original languageEnglish
Pages (from-to)2141-2152
JournalPolish Journal of Chemistry
Volume82
Issue number11
Publication statusPublished - 1 Nov 2008

Keywords

  • 3-Ethyl-lumiflavin
  • Crystal structure
  • Flavin
  • Photochemistry
  • Triplet state

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    Sikorska, E., Hernando, J., Bourdelande, J. L., Khmelinskii, I., Kubicki, M., Komasa, A., Prukała, D., & Sikorski, M. (2008). Flavin-related compounds: 3-Ethyl-lumiflavin. Combined DFT, NMR, X-ray and EI mass spectral study. Polish Journal of Chemistry, 82(11), 2141-2152.