Electrochemically-controlled hydrogen bonding. Selective recognition of urea and amide derivatives by simple redox-dependent receptors

Journal of the American Chemical Society

Volumn 118, Issue 16, 1996, Pages 3976-3977

  Ge, Yu ^a   Lilienthal, Ronald R ^a   Smith, Diane K ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; IMIDE; NAPHTHALENE DERIVATIVE; PHENANTHRENE DERIVATIVE; QUINONE DERIVATIVE; UREA DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ELECTROCHEMISTRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING;

EID: 0029989835     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954283k     Document Type: Article

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19. 2. Complicated aggregation is indicated since the NH protons shift upfieid at low concentrations and downfield at higher concentrations.
20. ox values cause increasingly larger changes in the simulated voltammograms and a decreasing fit to the experimental voltammograms.
21. The strong binding of 1 to the disubstituted ureas, particularily diphenylurea, may also be partly due to preorganization of these compounds for binding. AMI semiempincal molecular orbital calculations indicate that the "cis" conformation necessary for binding, with both N-H's pointing away from the carbonyl, is a low-energy conformation.
22. a's between the neutral receptor and the substrate to prevent proton transfer. Amides are particularily good in this regard since they are good H donors without being very acidic.
23. 3 and related compounds have been shown to form triple H-bonded complexes with the imide functional group in other compounds. Feibush, B.; Fiaueroa, A.; Charles, R.; Onan, K. D.; Feibush, P.; Karger, B. L. J. Am. Chem. Soc. 1986, 108, 3310. See also ref 7.
24. There are actually very few examples of purely organic, synthetic, redox-dependent receptor/substrate systems. See ref 16. To the best of our knowledge, the only other reported example of an organic receptor/substrate system where binding strength changes significantly with oxidation state is a viologen-based receptor that has been studied by us and others (ref 17).
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