Name: 2-Bromopropanenitrile. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Bromopropanenitrile, is researched, Molecular C3H4BrN, CAS is 19481-82-4, about Effect of Chemical Structure on the Electrochemical Cleavage of Alkoxyamines. Author is Hammill, Chelsey L.; Noble, Benjamin B.; Norcott, Philip L.; Ciampi, Simone; Coote, Michelle L..
A test set of 14 TEMPO-based alkoxyamines was studied via a combination of cyclic voltammetry (CV) and accurate quantum chem. to assess the effect of substituents on electrochem. cleavage. The exptl. oxidation potentials of the alkoxyamines fell into the range of 1.1-1.6 V vs. Ag/AgCl in acetonitrile, were well reproduced by theory (MAD 0.04V), with values showing good correlation with the σR Hammett parameters of both the R group and the OR group in TEMPO-R. Importantly, most of the studied alkoxyamines underwent oxidative cleavage to form either TEMPO• and R+ or TEMPO+ and =R•, with the former favored by electron donating substituents on R (e.g., 2-oxolane, Ac, CH(CH3)Ph, i-Pr, t-Bu) and the latter by electron withdrawing substituents (Bn, allyl, CH(CH3)C(O)OCH3, C(CH3)2C(O)OCH3, CH(CH3)CN). Where R is not stabilized (e.g. R = CH2C(O)OCH3, Me, Et), fully or almost fully reversible oxidation – without cleavage – was observed, making these species promising candidates for battery applications. Finally, in the case of R = Ph where N-O cleavage occurred, a phenoxy cation and an aminyl radical were generated. Based on these results, TEMPO-based alkoxy-amines can provide a variety of electrochem. generated carbon-centered radicals and carbocations for use in synthesis, polymerization and surface modification.
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