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Designing Synthetic Cationic Molecular Receptors for Alcohols
Author(s) -
Méndez Luis,
Singleton Raymond,
Slawin Alexandra M. Z.,
Stoddart J. Fraser,
Williams David J.,
Williams M. Kevin
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199204781
Subject(s) - cationic polymerization , alcohol , crown ether , hydrogen bond , ether , chemistry , receptor , stereochemistry , molecule , medicinal chemistry , polymer chemistry , organic chemistry , biochemistry , ion
The monoprotonation of diaza‐12‐crown‐6 derivatives converts these macrocycles to hosts for short‐chain alcohols; the association constant K a is as high as 47 M −1 . For the neutral diaza crown ether, on the other hand, K a is only 1.1 M −1 . X‐ray structure investigations show that the alcohol (R = Me) is held in place by two hydrogen bonds (see right). R = Me, Et, n Pr, n Bu; R′ = PhCH 2 , PhCH 2 CH 2
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