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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

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dc.contributor.authorSmith, C.
dc.contributor.authorStephens, A.
dc.contributor.authorWallwork, K.
dc.contributor.authorLincoln, S.
dc.contributor.authorTaylor, M.
dc.contributor.authorWainwright, K.
dc.date.issued2002
dc.descriptionCopyright © 2002 American Chemical Society
dc.description.abstractThe 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.
dc.description.statementofresponsibilityChristopher B. Smith, Ashley K. W. Stephens, Kia S. Wallwork, Stephen F. Lincoln, Max R. Taylor and Kevin P. Wainwright
dc.identifier.citationInorganic Chemistry, 2002; 41(5):1093-1100
dc.identifier.doi10.1021/ic010694s
dc.identifier.issn0020-1669
dc.identifier.issn1520-510X
dc.identifier.urihttp://hdl.handle.net/2440/4464
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.source.urihttps://doi.org/10.1021/ic010694s
dc.subjectCations, Divalent
dc.subjectCadmium
dc.subjectAzo Compounds
dc.subjectCarboxylic Acids
dc.subjectBenzoates
dc.subjectSalicylates
dc.subjectBenzene Derivatives
dc.subjectNitrophenols
dc.subjectOrganometallic Compounds
dc.subjectNaphthalenes
dc.subjectAmino Acids
dc.subjectPhenylalanine
dc.subjectLigands
dc.subjectCrystallography, X-Ray
dc.subjectMagnetic Resonance Spectroscopy
dc.subjectMolecular Structure
dc.subjectMolecular Conformation
dc.subjectStereoisomerism
dc.subjectHydrogen Bonding
dc.titleMetal 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
dc.typeJournal article
pubs.publication-statusPublished

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