title: The element effect in nucleophilic aromatic photosubstitution (SN2Ar*).
abstract: Photoreactions of 4-nitroanisole and the 2-halo-4-nitroanisoles (halogen = F, Cl, Br, I) with NaCN have been investigated. 4-Nitroanisole gave a novel, stable nitronate ion adduct (74%) with cyanide. For the five compounds, we report product distributions, Stern-Volmer kinetic plots, triplet lifetimes, and triplet yields, which afford rate constants for attack by the cyanide ion. Cyanide attack on the fluoride is diffusion controlled; the relative rates for attack at F, Cl, Br, and I are 27:2:2:1, respectively.
authors.affiliation: Department of Chemistry, University of Nebraska at Kearney, Kearney, Nebraska 68849, USA. wubbelsg@unk.edu
authors.forename: Gene G
authors.initials: GG
authors.lastname: Wubbels
authors.forename: Kandra M
authors.initials: KM
authors.lastname: Johnson
authors.forename: Travis A
authors.initials: TA
authors.lastname: Babcock