TY - JOUR
T1 - Intramolecular Electron Transfer and Dehalogenation of Nitroaromatic Anion Radicals1
AU - Bays, J. P.
AU - Blumer, S. T.
AU - Baral-Tosh, S.
AU - Behar, D.
AU - Neta, P.
PY - 1983/2
Y1 - 1983/2
N2 - A series of nitroaromatic compounds, containing Cl, Br, or tosyl groups at various positions, were synthesized and studied by pulse radiolysis in aqueous alcohol solutions. One-electron reduction of the compounds produces the anion radicals which then undergo an intramolecular electron transfer and eliminate X- (C1-, Br-, or TsO-). The rates of X- elimination vary over six orders of magnitude and are affected by the C-X bond dissociation energies, the size and nature of the group bridging the X with the π system, and the relative positions of these groups. Intramolecular electron transfer through space is also demonstrated.
AB - A series of nitroaromatic compounds, containing Cl, Br, or tosyl groups at various positions, were synthesized and studied by pulse radiolysis in aqueous alcohol solutions. One-electron reduction of the compounds produces the anion radicals which then undergo an intramolecular electron transfer and eliminate X- (C1-, Br-, or TsO-). The rates of X- elimination vary over six orders of magnitude and are affected by the C-X bond dissociation energies, the size and nature of the group bridging the X with the π system, and the relative positions of these groups. Intramolecular electron transfer through space is also demonstrated.
UR - http://www.scopus.com/inward/record.url?scp=0021098229&partnerID=8YFLogxK
U2 - 10.1021/ja00341a003
DO - 10.1021/ja00341a003
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
AN - SCOPUS:0021098229
SN - 0002-7863
VL - 105
SP - 320
EP - 324
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 3
ER -