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Amino–imino Tautomerization Reaction of the 4-Aminopyrimidine/acetic Acid System by Teruyoshi Kitamura; Masahiro Okita; Yutaka Sasaki; Hironori Ishikawa; Akira Fujimoto is a Chemistry article available to read on EtoBox.

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The amino-imino tautomerization of the 4-aminopyrimidine (4APM)/acetic acid (AcOH) system through dual hydrogen bonding in n-hexane at room temperature was investigated using UV absorption and fluorescence spectroscopies, fluorescence time-profile measurements, and molecular orbital calculations, with those of the imino-model compound of 3-methyl-4(1H)-pyrimidinimine (3M4PMI). From the experimental results, it was confirmed that the imino-tautomer was formed in the first excited singlet state (S1) state through the double-proton transfer of the dual hydrogen-bonded complex of 4APM with AcOH. The fluorescences of the free 4APM monomer (band maximum at 353 nm), imino-tautomer (at 414 nm), and 3M4PMI monomer (at 437 nm) exhibit the single-exponential decays of 98, 73, and 19 ps time constants, respectively. The shorter decay time of the imino-tautomer fluorescence compared with the free monomer one is suggestive of the low activation energy process in the S1 state. From the result of the shortest decay time of the 3M4PMI fluorescence, it can be deduced that 3M4PMI has a non-planar structure in the S1 state. The theoretical calculations on the S0 and S1 state double-proton transfer for

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Author

Teruyoshi Kitamura; Masahiro Okita; Yutaka Sasaki; Hironori Ishikawa; Akira Fujimoto

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Pergamon Press Ltd.; Elsevier BV (ISSN 1386-1425)

Published

2008

Language

EN

Field

Chemistry (Physical Sciences)