The Influence Of Cation Pi Interactions On Singlet Oxygen Reaction Rates
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The Influence of Cation-pi Interactions on Singlet Oxygen Reaction Rates
Singlet oxygen (1O2, 1Delta g) is a high-energy metastable variant of molecular oxygen that is often generated in vivo as a byproduct of the many reactions that make life possible. Ever-increasing human exposure to 1O2, partly stemming from growing concentrations of environmental pollutants in urban areas and higher levels of exposure to UV radiation, however, have rendered 1O2 a more serious threat to human life. Because 1O2 is capable of reacting with a wide array of substrates, chronic exposure to 1O2 can cause diseases by repeatedly damaging molecules like DNA, RNA, lipids, and proteins. The indole moiety of the protein residue tryptophan, for example, has a high 1O 2 chemical quenching rate and is readily converted to kynurenine and N'-formyl kynurenine upon 1O2 exposure. It is known that aromatic molecules like tryptophan can form strong electrostatic interaction like cation--pi, but it is unknown if cation--pi interactions can influence 1O2 chemical quenching rates. Therefore, this study aims to determine if the cation--pi interaction can affect chemical quenching rates of 1O2 with aromatic molecules. We report here the reactivity of N,N'-bis(2-(3-indolyl)ethyl-4,13-diaza-18-crown-6 ether with 1O2, a crown ether known to form well characterized cation--pi interactions in solution, to demonstrate that cation--pi interactions influence the chemical quenching rates of an indole moiety, even when the indole is fully exposed in solution.
Advances in Physical Organic Chemistry
Advances in Physical Organic Chemistry provides the chemical community with authoritative and critical assessments of the many aspects of physical organic chemistry. The field is a rapidly developing one, with results and methodologies finding application from biology to solid state physics. * Reviews the application of quantitative and mathematical methods towards understanding chemical problems * Multidisciplinary volumes cover organic, organometallic, bioorganic, enzymes and materials topics