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Volumn 11, Issue 20, 2005, Pages 6080-6094

Anion recognition by neutral macrocyclic amides

Author keywords

Amides; Anions; Hydrogen bonds; Macrocyclic ligands

Indexed keywords

CARBOXYLIC ACIDS; HYDROGEN BONDS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 26844509289     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500232     Document Type: Article
Times cited : (166)

References (86)
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    • For review on macrocyclic anion receptors based on hydrogen-bonding interactions, see: K. Choi, A. D. Hamilton, Coord. Chem. Rev. 2003, 240, 101-110.
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    • Choi, K.1    Hamilton, A.D.2
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    • See ref. [2h], Chapter 3
    • See ref. [2h], Chapter 3.
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    • b) very recently it has been shown that low-temperature nucleophil ic aromatic substitution could be used to generate anhydrous tetra-butylammonium fluoride in aprotic solvents: H. Sun, S. G. DiMagno, J. Am. Chem. Soc. 2005, 127, 2050-2051.
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    • Sun, H.1    DiMagno, S.G.2
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    • note
    • For other examples of proton-fluoride coupling through hydrogen bonds in NMR spectra, see ref. [36] and references therein.
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    • note
    • [48b] and therefore we assumed that bifluoride comes mainly from ligand deprotonation. Indeed, control experiment showed no increase in bifluoride content in the tetrabutylammonium fluoride solution over a few hours.
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    • note
    • [33b] demonstrated that the presence of anion receptors can increase the acidity of weak acids through stabilization of their conjugate anions. We suppose that in an analogous but opposite way, the presence of anions may decrease the acidity of weakly acidic receptors, stabilizing their protonated forms. Such stabilization is anticipated to be larger for better receptors, presumably bicyclic ones in the present case.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.