Please use this identifier to cite or link to this item: https://doi.org/10.1021/jp073142p
Title: Reaction of the radical pair NO2 .; and CO 3 .- with 2-[6-(4′-Amino)phenoxy-3H-xanthen-3-on-9- yl]benzoic acid (APF)
Authors: Mak, A.M.
Whiteman, M.
Wong, M.W. 
Issue Date: 23-Aug-2007
Source: Mak, A.M., Whiteman, M., Wong, M.W. (2007-08-23). Reaction of the radical pair NO2 .; and CO 3 .- with 2-[6-(4′-Amino)phenoxy-3H-xanthen-3-on-9- yl]benzoic acid (APF). Journal of Physical Chemistry A 111 (33) : 8202-8210. ScholarBank@NUS Repository. https://doi.org/10.1021/jp073142p
Abstract: The fluorogenic indicator 2-[6-(4′-amino)phenoxy-3H-xanthen-3-on-9- yl]benzoic acid (APF) is used widely to detect and measure reactive nitrogen and oxygen species such as peroxynitrite, ONOO-, both in vivo and in vitro. We present in this work the results of a combined computational and experimental study to provide insights into the mechanism of the reaction of APF with the radical products of ONOO- reaction with CO2, namely NO2 . and CO3 .-. The experimental study on the inhibition of APF oxidation by HCO3 - suggests that a direct reaction of APF with nitrosoperoxycarbonate, ONOOCO2 -, is unlikely. The mechanism of APF action on NO2 . and CO3 .- was investigated using gas-phase and solvent modeled calculations at the MPW1K/ 6-311+G(d)//MPW1K/6-31G(d) level of theory. Our computational results suggest that two-electron oxidation of APF takes place in two rapid one-electron oxidation steps, the first being a proton-coupled electron transfer (PCET) between APF and NO2 ., followed by addition of CO 3 .- and subsequent decomposition of the adduct to yield fluorescein. © 2007 American Chemical Society.
Source Title: Journal of Physical Chemistry A
URI: http://scholarbank.nus.edu.sg/handle/10635/94668
ISSN: 10895639
DOI: 10.1021/jp073142p
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