Cargando…

Interfacial Oxidative Oligomerization of Catechol

[Image: see text] The heterogeneous reaction between thin films of catechol exposed to O(3)(g) creates hydroxyl radicals (HO(•)) in situ, which in turn generate semiquinone radical intermediates in the path to form heavier polyhydroxylated biphenyl, terphenyl, and triphenylene products. Herein, the...

Descripción completa

Detalles Bibliográficos
Autores principales: Guzman, Marcelo I., Pillar-Little, Elizabeth A., Eugene, Alexis J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9558612/
https://www.ncbi.nlm.nih.gov/pubmed/36249361
http://dx.doi.org/10.1021/acsomega.2c05290
Descripción
Sumario:[Image: see text] The heterogeneous reaction between thin films of catechol exposed to O(3)(g) creates hydroxyl radicals (HO(•)) in situ, which in turn generate semiquinone radical intermediates in the path to form heavier polyhydroxylated biphenyl, terphenyl, and triphenylene products. Herein, the alteration of catechol aromatic surfaces and their chemical composition are studied during the heterogeneous oxidation of catechol films by O(3)(g) molar ratios ≥ 230 ppbv at variable relative humidity levels (0% ≤ RH ≤ 90%). Fourier transform infrared micro-spectroscopy, atomic force microscopy, electrospray ionization mass spectrometry, and reverse-phase liquid chromatography with UV–visible and mass spectrometry detection provide new physical insights into understanding the surface reaction. A Langmuir–Hinshelwood mechanism is accounted to report reaction rates, half-lives, and reactive uptake coefficients for the system under variable relative humidity levels. The reactions reported explain how the oligomerization of polyphenols proceeds at interfaces to contribute to the formation of brown organic carbon in atmospheric aerosols.