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Photochemical syn-anti isomerization reaction in N4-hydroxycytosine. An experimental matrix isolation and theoretical study
Authors:Lapinski L  Nowak M J  Adamowicz L
Affiliation:Institute of Physics, Polish Academy of Sciences, Al. Lotnikow 32/46, 02-668 Warsaw, Poland.
Abstract:Infrared spectra of N4-hydroxycytosine isolated in argon and nitrogen low-temperature matrixes are reported. The compound was found to adopt the syn structure of the imino-oxo tautomeric form exclusively. A photoreaction (lambda > 250 nm) converting this form into the anti isomer was observed. The reaction is reversible and leads to a photostationary point. The initial infrared spectrum and the spectrum of the photoproduct were assigned to the syn and anti isomers, respectively. This assignment is based on a close agreement between the experimental spectra and the spectra theoretically simulated at the DFT(B3LYP)/6-31++G** level of theory.
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