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Molecular design using electrostatic interactions. Part 4: Synthesis and properties of flexible tetrapodand tetracations derived from naphthalene. Role of structured water in the electrostatic binding of polyanion guests: a model for interactions in biological systems

Christofi, AM; Garratt, PJ; Hogarth, G; Ibbett, AJ; Ng, YF; Steed, JW; (2002) Molecular design using electrostatic interactions. Part 4: Synthesis and properties of flexible tetrapodand tetracations derived from naphthalene. Role of structured water in the electrostatic binding of polyanion guests: a model for interactions in biological systems. TETRAHEDRON , 58 (22) 4543 - 4549.

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Abstract

The 1,4,5,8-tetracations 5 and 11 have been prepared from 1,4,5,8-tetrakis(bromomethyl)naphthalene and 1,4,5,8-tetrakis(bromomethyl)-2,3,6,7-tetramethylnaphthalene, respectively by treatment with DABCO in acetonitrile. Their interactions with the benzene-1,2,4,5-tetracarboxyl ate and naphthalene-1,4,5,8-tetracarboxylate tetraanions in water were investigated by H-1 NMR titration and both tetracations were found to have greater binding affinity to the benzene tetracarboxylate. Both also gave precipitates with ferricyanide but only the naphthalene tetracation 5 gave a precipitate with ferrocyanide. The X-ray structure of the crystalline ferricyanide tetracation 14 from tetra-methylnaphthalene showed the methylDABCO cationic anus to be alternately above and below the naphthalene ring, which was itself distorted from the plane. The bound water in the non-charge-matched complex 14 appears to have a more intimate role in the crystal structure than does the bound water in the charge-matched ferricyanide 15 derived from 2,4,6-tris(DABCO-N-methyl)mesitylene tribromide which we reported previously. An analogy with interactions in biological receptors is made. (C) 2002 Elsevier Science Ltd. All rights reserved.

Type:Article
Title:Molecular design using electrostatic interactions. Part 4: Synthesis and properties of flexible tetrapodand tetracations derived from naphthalene. Role of structured water in the electrostatic binding of polyanion guests: a model for interactions in biological systems
Keywords:molecular recognition, tetracations, ferricyanides, X-ray crystal structures, PROTEIN-DNA INTERACTIONS, RESTRICTED CONFORMATIONS, PEPTIDE BINDING, ANTIBODY, OCTAMETHYLNAPHTHALENE, THERMODYNAMICS, SPECIFICITY, RECOGNITION, ASSOCIATION, ANTIGEN
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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