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- W2046001892 abstract "Abstract Efficient excited-state intramolecular proton transfer (ESIPT) in 2-(2′-hydroxy-5′-methylphenyl)-3,3-dimethyl-3H-indole (HBC) leads to the formation of an unstable trans-keto tautomer 1 K tr whose transient absorption can be observed in flash experiments. The assignment of this transient absorption to the trans-keto tautomer is corroborated by the observation that a similar transient is not formed from BHBC, which has been synthesized as a bridged, rotationally blocked counterpart of HBC. In hydrocarbon solvents, two 1 K tr molecules revert by a mutual hydrogen-exchange reaction to the stable enol form of HBC. This second-order reaction is diffusion-controlled and its rate constant is proportional to T /η over a wide range of the solvent viscosity η. In the presence of alcohols (ROH) a first-order, pseudo-monomolecular proton-catalysed re-enolization reaction competes with the second-order reaction. With methanol and ethanol as proton donors it is shown that two donor molecules are involved in this process. The rate of the proton-catalysed reaction increases with decreasing temperatures. A pre-equilibrium between a nonreactive 1 K tr and a reactive 1 K tr ::: (ROH) 2 complex is the reason for this unusual temperature dependence of the first-order 1 K tr decay rate." @default.
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- W2046001892 date "1994-09-01" @default.
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- W2046001892 title "Flash-photolysis of 2-(2′-hydroxyphenyl)-3-H-indole. Ground-state keto-enol tautomerization by mutual hydrogen exchange and by proton catalysis" @default.
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- W2046001892 doi "https://doi.org/10.1016/0301-0104(94)01624-0" @default.
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