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Neutral Anion Receptors with Multiple Urea‐Binding Sites
Author(s) -
SnellinkRuël Bianca H. M.,
Antonisse Martijn M. G.,
Engbersen Johan F. J.,
Timmerman Peter,
Reinhoudt David N.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200001)2000:1<165::aid-ejoc165>3.0.co;2-#
Subject(s) - chemistry , urea , receptor , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry
The synthesis of macrocyclic and acyclic cleft‐like anion receptors in which four hydrogen bond donating urea moieties are present in a preorganized fashion is described. NMR spectroscopy shows the complex formation with H 2 PO 4 − and Cl − . Cleft‐like receptors bind H 2 PO 4 − in a 2:1 guest‐host stoichiometry ( K a = 10 7 M −2 ) in DMSO, whereas Cl − is bound in a 1:1 stoichiometry ( K a = 10 3 M −1 ). The macrocyclic receptors form a 1:1 complex with H 2 PO 4 − ( K a = 10 3 M −1 in DMSO) with a 100‐fold selectivity for H 2 PO 4 − over Cl − .