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Volumn 74, Issue 11, 2009, Pages 4350-4353

Calix[5]arene-based heteroditopic receptor for 2-phenylethylamine hydrochloride

Author keywords

[No Author keywords available]

Indexed keywords

CALIX[5]ARENE; CHEMICAL EQUATIONS; HETERODITOPIC RECEPTORS; ION PAIRS; ORGANIC SALT; PHENYLETHYLAMINE; UREIDO MOIETIES;

EID: 66249096302     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802777v     Document Type: Article
Times cited : (44)

References (80)
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    • Calix[4]pyrroles have been found to act by themselves as heteroditopic receptors. For a recent example, see
    • Calix[4]pyrroles have been found to act by themselves as heteroditopic receptors. For a recent example, see: Tong, C. C.; Quesada, R.; Sessler, J. L.; Gale, P. A. Chem. Commun. 2008, 6321-6323.
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    • It has been shown that contact ion-pair complexation, that is, when a heteroditopic receptor is able to accommodate the two ions without breaking the ion pair, is generally energetically more efficient, since there is no Coulombic energy penalty resulting from charge separation. Contact ion-pair heteroditopic receptors, however, tend to be very selective towards the specific salt they have been designed for but often do not tolerate even minute structural variation on either of the ionic components, see
    • It has been shown that contact ion-pair complexation, that is, when a heteroditopic receptor is able to accommodate the two ions without breaking the ion pair, is generally energetically more efficient, since there is no Coulombic energy penalty resulting from charge separation. Contact ion-pair heteroditopic receptors, however, tend to be very selective towards the specific salt they have been designed for but often do not tolerate even minute structural variation on either of the ionic components, see: Lankshear, M. D.; Dudley, I. M.; Chan, K.-M.; Cowley, A. R.; Santos, S. M.; Felix, V.; Beer, P. D. Chem. - Eur. J. 2008, 14, 2248-2263.
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    • a values were derived from the average of at least three independent measurements (standard error ±15%)
    • a values were derived from the average of at least three independent measurements (standard error ±15%).
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    • The presence of bis-crown-3 ether moieties is known to reduce molecular motion in the calix[4]arene series, see: Arduini, A.; Fabbi, M.; Mantovani, M.; Mirone, L.; Pochini, A.; Secchi, A.; Ungaro, R. J. Org. Chem. 1995, 60, 1454-1457.
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    • +.
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    • +⊂10] complexes were found to be broad, as a result of a faster exchange rate with respect to the other cations. Addition of an excess of sodium picrate resulted, however, in a sharpening of the peaks. This is not the first example observed for calixcrowns, see
    • +⊂10] complexes were found to be broad, as a result of a faster exchange rate with respect to the other cations. Addition of an excess of sodium picrate resulted, however, in a sharpening of the peaks. This is not the first example observed for calixcrowns, see: Arnaud-Neu, F.; Ferguson, G.; Fuangswasdi, S.; Notti, A.; Pappalardo, S.; Parisi, M. F.; Petringa, A. J. Org. Chem. 1998, 63, 7770-7779.
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    • 3 to be able to observe the NH resonances and maximize, at the same time, the anion-ureido binding interactions
    • 3 to be able to observe the NH resonances and maximize, at the same time, the anion-ureido binding interactions.
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    • 3OD, and consequently their resonances are not observable
    • 3OD, and consequently their resonances are not observable.
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    • Host-guest complexation was judged to take place with a 1:1 stoichiometry on the basis of the fact that the addition of an excess of guest salt (2 equiv) to 10 (1 equiv) caused the disappearance of all the resonances accounting for the free host and did not induce any detectable chemical shift variation on those referring to the complexed species
    • Host-guest complexation was judged to take place with a 1:1 stoichiometry on the basis of the fact that the addition of an excess of guest salt (2 equiv) to 10 (1 equiv) caused the disappearance of all the resonances accounting for the free host and did not induce any detectable chemical shift variation on those referring to the complexed species.
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    • +complex
    • +complex.
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    • and references therein
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.