Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas
Journal of the American Chemical Society, ISSN: 0002-7863, Vol: 127, Issue: 17, Page: 6423-6429
2005
- 88Citations
- 43Captures
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Metrics Details
- Citations88
- Citation Indexes88
- 88
- CrossRef69
- Captures43
- Readers43
- 43
Article Description
Reduction of nitrobenzene derivatives in the presence of arylureas in aprotic solvents results in large positive shifts in potential of the nitrobenzene cyclic voltammetry wave with little change in wave shape. This behavior is indicative of reversible hydrogen bonding between nitrobenzene radical anions and arylureas. Computer fitting of the cyclic voltammetry of 4-nitroaniline, NA, plus 1,3-diphenylurea in DMF shows essentially no binding between urea and NA in the oxidized state (K < 1 M), but very strong binding in the reduced state (K = 8 × 10 M), along with very rapid rates of hydrogen bond formation (k′s ≈ 10 -10 M s), making this system a fast on/off redox switch. © 2005 American Chemical Society.
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