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1 September 2005 Unimolecular Photochemistry of 4-Thiouracils
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Abstract

Unimolecular phototautomeric reactions in 4-thiouracil, 1-methyl-4-thiouracil and 6-aza-4-thiouracil were studied using the matrix-isolation technique combined with infrared absorption spectroscopy. For monomers of these compounds, isolated in solid argon at 10 K, an intramolecular proton-transfer photoreaction was observed. Upon UV (λ > 345 nm) irradiation, the initial oxo–thione forms of 4-thiouracils were converted into the corresponding oxo–thiol tautomers. The photogenerated oxo–thiol isomers were identified by comparing their experimental IR spectra with the spectra theoretically calculated at the DFT(B3LYP)/6-311 G(2d,p) level. Good agreement between the observed and predicted pattern of spectral bands allowed a reliable identification. This is the first report on experimental observation of isomeric forms of 4-thiouracils other than the canonical oxo–thione tautomers.

Artem Khvorostov, Leszek Lapinski, Hanna Rostkowska, and Maciej J. Nowak "Unimolecular Photochemistry of 4-Thiouracils," Photochemistry and Photobiology 81(5), 1205-1211, (1 September 2005). https://doi.org/10.1562/2005-05-19-RA-534
Received: 19 May 2005; Accepted: 1 June 2005; Published: 1 September 2005
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