Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
9634212 | Journal of Electroanalytical Chemistry | 2005 | 5 Pages |
Abstract
The reductions of 2-naphthaldehyde, (3), 9,9â²-spirobi-(9H-fluorene)-2-carboxaldehyde, (2), and 2-fluorenecarboxaldehyde, (4), have been studied in N,N-dimethylformamide (DMF) and acetonitrile. Putative spiroconjugation was the source of interest in 2 and its formal potential for the neutral/radical anion couple and the rate constant for dimerization of the radical anions were compared with the same quantities for 3 and 4. In DMF the range of formal potentials for 2-4 is only 100 mV and the rate constants for the three aldehydes differ by a factor of two. These small differences are consistent with insignificant spiroconjugative effects. The effect of added water on the dimerization rate constant for the radical anions of 3 has been interpreted in terms of reversible dimerization to a dimer dianion followed by irreversible protonation of the dianion by water.
Related Topics
Physical Sciences and Engineering
Chemical Engineering
Chemical Engineering (General)
Authors
Charles C. Van Kirk, Giulia Fioravanti, Leonardo Mattiello, Liliana B. Rampazzo, Norma A. MacÃas-Ruvalcaba, Dennis H. Evans,