Literature DB >> 16967979

Calix[4]pyrrole as a chloride anion receptor: solvent and countercation effects.

Jonathan L Sessler1, Dustin E Gross, Won-Seob Cho, Vincent M Lynch, Franz P Schmidtchen, Gareth W Bates, Mark E Light, Philip A Gale.   

Abstract

The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and (1)H NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K(a)), on the other hand, were found to be highly dependent on the choice of solvent with K(a)'s ranging from 10(2)-10(5) M(-1) being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the K(a)'s for the interaction with chloride ranging from 10(2)-10(4) M(-1). In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.

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Year:  2006        PMID: 16967979      PMCID: PMC2572717          DOI: 10.1021/ja064012h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  Surprises in the energetics of host-guest anion binding to calix[4]pyrrole.

Authors:  Franz P Schmidtchen
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

2.  Selective recognition of an alkali halide contact ion-pair.

Authors:  J M Mahoney; A M Beatty; B D Smith
Journal:  J Am Chem Soc       Date:  2001-06-20       Impact factor: 15.419

3.  On the value of c: can low affinity systems be studied by isothermal titration calorimetry?

Authors:  W Bruce Turnbull; Antonio H Daranas
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419

4.  Theoretical study of anion binding to calix[4]pyrrole: the effects of solvent, fluorine substitution, cosolute, and water traces.

Authors:  J Ramón Blas; Manuel Márquez; Jonathan L Sessler; F Javier Luque; Modesto Orozco
Journal:  J Am Chem Soc       Date:  2002-10-30       Impact factor: 15.419

5.  A study of statistical error in isothermal titration calorimetry.

Authors:  Joel Tellinghuisen
Journal:  Anal Biochem       Date:  2003-10-01       Impact factor: 3.365

6.  Optimizing experimental parameters in isothermal titration calorimetry.

Authors:  Joel Tellinghuisen
Journal:  J Phys Chem B       Date:  2005-10-27       Impact factor: 2.991

7.  Anion-anion assembly: a new class of anionic supramolecular polymer containing 3,4-dichloro-2,5-diamido-substituted pyrrole anion dimers.

Authors:  Philip A Gale; Korakot Navakhun; Salvatore Camiolo; Mark E Light; Michael B Hursthouse
Journal:  J Am Chem Soc       Date:  2002-09-25       Impact factor: 15.419

8.  Fluoride-selective binding in a new deep cavity calix[4]pyrrole: experiment and theory.

Authors:  Christopher J Woods; Salvatore Camiolo; Mark E Light; Simon J Coles; Michael B Hursthouse; Michael A King; Philip A Gale; Jonathan W Essex
Journal:  J Am Chem Soc       Date:  2002-07-24       Impact factor: 15.419

9.  Solution and solid-state studies of 3,4-dichloro-2,5-diamidopyrroles: formation of an unusual anionic narcissistic dimer.

Authors:  Salvatore Camiolo; Philip A Gale; Michael B Hursthouse; Mark E Light; Andy J Shi
Journal:  Chem Commun (Camb)       Date:  2002-04-07       Impact factor: 6.222

10.  Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour, anion binding and colour change signalled deprotonation.

Authors:  Salvatore Camiolo; Philip A Gale; Michael B Hursthouse; Mark E Light
Journal:  Org Biomol Chem       Date:  2003-02-21       Impact factor: 3.876

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  24 in total

1.  Spectroscopic, structural, and theoretical studies of halide complexes with a urea-based tripodal receptor.

Authors:  Avijit Pramanik; Douglas R Powell; Bryan M Wong; Md Alamgir Hossain
Journal:  Inorg Chem       Date:  2012-03-12       Impact factor: 5.165

2.  Experimental and Theoretical Aspects of Anion Complexes with a Thiophene-Based Cryptand.

Authors:  Syed A Haque; Musabbir A Saeed; Afsana Jahan; Jing Wang; Jerzy Leszczynski; Md Alamgir Hossain
Journal:  Comments Mod Chem A Comments Inorg Chem       Date:  2016-02-28       Impact factor: 4.533

3.  Benzene-, pyrrole-, and furan-containing diametrically strapped calix[4]pyrroles--an experimental and theoretical study of hydrogen-bonding effects in chloride anion recognition.

Authors:  Dae-Wi Yoon; Dustin E Gross; Vincent M Lynch; Jonathan L Sessler; Benjamin P Hay; Chang-Hee Lee
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 4.  Artificial receptors for the recognition of phosphorylated molecules.

Authors:  Amanda E Hargrove; Sonia Nieto; Tianzhi Zhang; Jonathan L Sessler; Eric V Anslyn
Journal:  Chem Rev       Date:  2011-09-12       Impact factor: 60.622

5.  Bis-cation salt complexation by meso-octamethylcalix[4]pyrrole: linking complexes in solution and in the solid state.

Authors:  Claudia Caltagirone; Nathan L Bill; Dustin E Gross; Mark E Light; Jonathan L Sessler; Philip A Gale
Journal:  Org Biomol Chem       Date:  2009-11-04       Impact factor: 3.876

6.  Synthesis and anion binding studies of tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors: Proton transfer-induced selectivity for hydrogen sulfate over sulfate.

Authors:  Maryam Emami Khansari; Corey R Johnson; Ismet Basaran; Aemal Nafis; Jing Wang; Jerzy Leszczynski; Md Alamgir Hossain
Journal:  RSC Adv       Date:  2015-01-29       Impact factor: 3.361

7.  Uranyl dication mediated photoswitching of a calix[4]pyrrole-based metal coordination cage.

Authors:  Juhoon Lee; James T Brewster; Bo Song; Vincent M Lynch; Inhong Hwang; Xiaopeng Li; Jonathan L Sessler
Journal:  Chem Commun (Camb)       Date:  2018-08-21       Impact factor: 6.222

8.  meso-octamethylcalix[4]pyrrole: an old yet new transmembrane ion-pair transporter.

Authors:  Christine C Tong; Roberto Quesada; Jonathan L Sessler; Philip A Gale
Journal:  Chem Commun (Camb)       Date:  2008-10-21       Impact factor: 6.222

9.  Selective sensing of anions with calix[4]pyrroles strapped with chromogenic dipyrrolylquinoxalines.

Authors:  Jaeduk Yoo; Min-Soo Kim; Seong-Jin Hong; Jonathan L Sessler; Chang-Hee Lee
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

10.  Carboxylate anion diminishes chloride transport through a synthetic, self-assembled transmembrane pore.

Authors:  Lei You; Riccardo Ferdani; Ruiqiong Li; Joseph P Kramer; Rudolph Ernst K Winter; George W Gokel
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

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