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Type: Journal article
Title: Metal ion-dependent molecular inclusion chemistry: Inclusion of aromatic anions by coordinated 1,4,7,10-Tetrakis ((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane
Author: Smith, C.
Stephens, A.
Wallwork, K.
Lincoln, S.
Taylor, M.
Wainwright, K.
Citation: Inorganic Chemistry, 2002; 41(5):1093-1100
Publisher: Amer Chemical Soc
Issue Date: 2002
ISSN: 0020-1669
Statement of
Christopher B. Smith, Ashley K. W. Stephens, Kia S. Wallwork, Stephen F. Lincoln, Max R. Taylor and Kevin P. Wainwright
Abstract: The ability of the pendant donor macrocyclic ligand 1,4,7,10-tetrakis((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraaza- cyclododecane((S)-thphpc12) (or [Cd((S)-thphpc12)](2+)) to act as a metal ion-dependent receptor for aromatic anions has been investigated in solution and in the solid state. [Cd((S)-thphpc12)](2+) adopts a stable conical conformation with a large hydrophobic cavity, which has been shown to contain, via complementary multiple hydrogen bonding, p-nitrophenolate, aromatic carboxylates, p-toluenesulfonate, certain aromatic amino acid anions, phenoxyacetate, and acetate. In the case of p-nitrophenolate only, one or two anions can be contained within the receptor cavity. The crystal structure of [Cd((S)-thphpc12)(p-nitrophenolate)(2)] shows a coplanar arrangement of the p-nitrophenolates, where each is retained in the cavity by a pair of hydrogen bonds to cis hydroxyl groups. The crystal structure of the p-aminobenzoate inclusion complex indicates retention of the guest via a pair of hydrogen bonds to each oxygen atom of the carboxylate moiety. The crystal structure of the (L)-phenylalaninate inclusion complex indicates that the amino acid is retained by five hydrogen bonds, two involving the nitrogen atom and three to the oxygen atoms of the carboxylate moiety. Binding constants (10(3)-10(5) M(-1)) for the inclusion of some of the aforementioned anions in [Cd((S)-thphpc12)](2+) and related receptors were measured by (1)H NMR titration in DMSO-d(6) at 298 K.
Keywords: Cations, Divalent; Cadmium; Azo Compounds; Carboxylic Acids; Benzoates; Salicylates; Benzene Derivatives; Nitrophenols; Organometallic Compounds; Naphthalenes; Amino Acids; Phenylalanine; Ligands; Crystallography, X-Ray; Magnetic Resonance Spectroscopy; Molecular Structure; Molecular Conformation; Stereoisomerism; Hydrogen Bonding
Description: Copyright © 2002 American Chemical Society
RMID: 0020020604
DOI: 10.1021/ic010694s
Appears in Collections:Chemistry publications
Environment Institute publications

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