Abstract
N-2-Nitrobenzylmonoaza-15-crown-5 (2) and N-4-Nitrobenzylmonoaza-15-crown-5, representatives of a new class of N-pivot lariat ethers bearing reducible nitroaromatic side arms, have been prepared and examined by cyclic voltammetric techniques. When the nitro group is sterically disposed to permit interaction with the ring-bound cation, intramolecular ion pairing occurs. This is not the case when the side arm is remote from the macroring nor when the side arm is detached. A thermochemical cycle is used to determine that the binding constant (K//s) enhancement in MeCN solution is 25,000-fold upon electrochemical switching.
Original language | English (US) |
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Pages (from-to) | 1633-1635 |
Number of pages | 3 |
Journal | Journal of the American Chemical Society |
Volume | 106 |
Issue number | 6 |
DOIs | |
State | Published - Mar 1 1984 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry