Acid-Catalyzed Electron Transfer Processes in Naphthalene peri-Dichalcogenides

The Journal of Organic Chemistry
Tyler A TuckThomas G Back

Abstract

1,8-Naphthalene peri-dichalcogenides undergo protonation by Bronsted acids to produce electrophilic cations. Single electron transfer (SET) from the remaining unprotonated electron-rich peri-dichalcogenide to the cation then generates a radical cation and a radical. Thus, the formation of radical species results in severe peak broadening and coalescence of NMR signals when trifluoroacetic acid or other strong acids are added to the peri-dichalcogenide, and the process can be reversed by treatment with base. Further evidence for the formation of radicals stems from EPR, radical quencing with sodium dithionite, and computational experiments. The electron transfer is enhanced by the presence of 2,7-dialkoxy substituents that further increase the electron-donating ability of the dichalcogenides. This is an unusual example of a proton-coupled electron transfer process where an electron-rich molecule reacts with its own conjugate acid via a single electron transfer process.

References

Feb 9, 1973·Science·J T RotruckW G Hoekstra
May 15, 1973·FEBS Letters·L FloheH H Schock
Jan 1, 1984·Methods in Enzymology·H E Ganther, R J Kraus
Jun 1, 1983·European Journal of Biochemistry·O EppA Wendel
Aug 12, 1998·Biochemistry·D M LuykxS de Vries
Oct 27, 2001·Organic Letters·R S GraingerJ W Steed
Apr 1, 2004·Chemistry : a European Journal·Stephen M AucottJ Derek Woollins
Oct 16, 2004·Dalton Transactions : an International Journal of Inorganic Chemistry·Stephen M AucottJ Derek Woollins
Feb 16, 2005·Biochemical Pharmacology·Hans NohlKatrin Staniek
Aug 14, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Birgit MuellerKonrad Seppelt
Jun 9, 2011·Journal of the American Chemical Society·Debasish Manna, Govindasamy Mugesh
Jun 19, 2012·Chemical Reviews·David R WeinbergThomas J Meyer
Jul 5, 2012·Annals of the New York Academy of Sciences·Regina Brigelius-Flohé, Anna Patricia Kipp
Apr 17, 2013·Angewandte Chemie·Gengjie Lin, Lei Li
Jun 5, 2013·Journal of Medicinal Chemistry·Steven R LaPlantePierre L Beaulieu
Aug 19, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Belinda Heyne
Aug 20, 2016·Organic & Biomolecular Chemistry·Santanu Mondal, Govindasamy Mugesh

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