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Journal Article

Conformationally protected hydrazine radical cations and the gearing effect on a hydrazine electron-transfer reaction

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Neugebauer,  Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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http://pubs.acs.org/doi/pdf/10.1021/ja00076a020
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https://dx.doi.org/10.1021/ja00076a020
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Citation

Nelsen, S. F., Chen, L. J., Petillo, P. A., Evans, D. H., & Neugebauer, F. A. (1993). Conformationally protected hydrazine radical cations and the gearing effect on a hydrazine electron-transfer reaction. Journal of the American Chemical Society, 115(23), 10611-10620. doi:10.1021/ja00076a020.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-A9F8-7
Abstract
The N-isopropylated hydrazine radical cations from 7 (22/tBu,iPr) and 9 (22/iPr2) are isolable and are the first examples of isolable hydrazine radical cations which lack all C,-H bonds being protected as bridgehead carbons in bicyclic rings. The cyclic voltammogram of 9 shows electrochemically irreversible oxidation and reduction waves at platinum. It is argued that this results from a gearing effect of the isopropyl groups, which causes the radical cation from neutral 9 to be generated in an unstable conformation. Kinetic and thermodynamic conformational effects which cause hydrazine cyclic voltammetry curves to be electrochemically irreversible are contrasted