title: Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control.
abstract: The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. (1)H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π2 orbital can occur to stabilize the developing sulfur radical cation.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Takuhei
authors.initials: T
authors.lastname: Yamamoto
authors.affiliation: Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Jixun
authors.initials: J
authors.lastname: Dai
authors.affiliation: Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Neil E
authors.initials: NE
authors.lastname: Jacobsen
authors.affiliation: Department of Chemistry, The University of Kansas , Lawrence, Kansas 66045, United States.
authors.forename: Malika
authors.initials: M
authors.lastname: Ammam
authors.affiliation: Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Gabriel B
authors.initials: GB
authors.lastname: Hall
authors.affiliation: Department of Pharmaceutical Chemistry, The University of Kansas , Lawrence, Kansas 66047, United States.
authors.forename: Olivier
authors.initials: O
authors.lastname: Mozziconacci
authors.affiliation: Department of Pharmaceutical Chemistry, The University of Kansas , Lawrence, Kansas 66047, United States.
authors.forename: Christian
authors.initials: C
authors.lastname: Schöneich
authors.affiliation: Department of Chemistry, The University of Kansas , Lawrence, Kansas 66045, United States.
authors.forename: George S
authors.initials: GS
authors.lastname: Wilson
authors.affiliation: Department of Chemistry and Biochemistry, The University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Richard S
authors.initials: RS
authors.lastname: Glass