Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole

Ellis, Ross J.; Reinhart, Benjamin; Williams, Neil J.; Moyer, Bruce A.; Bryantsev, Vyacheslav S.

doi:10.1039/C7CC02347B

Title: Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole

Abstract

The role of solvent in molecular recognition systems is under-researched and often ignored, especially when the solvent is considered “non-interacting”. This study concerns the role of toluene solvent in cesium(I) recognition by calix[4]pyrrole. We show that π-donor interactions bind toluene molecules onto the open face of the cation-receptor complex, thus “capping the calix.” As a result, by characterizing this unusual aromatically-saturated complex, we show how “non-interacting” aromatic solvents can directly coordinate receptor-bound cations and thus influence recognition.

Authors:

Ellis, Ross J. ^[1]; Reinhart, Benjamin ^[2]; Williams, Neil J. ^[3]; Moyer, Bruce A. ^[1];

^[1]

Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States)

Publication Date:: Thu May 04 00:00:00 EDT 2017

Research Org.:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Chemical Sciences, Geosciences, and Biosciences Division

OSTI Identifier:: 1367215

Grant/Contract Number:: AC02-06CH11357

Resource Type:: Accepted Manuscript

Journal Name:: ChemComm

Additional Journal Information:: Journal Volume: 53; Journal Issue: 41; Journal ID: ISSN 1359-7345

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; separation sciences

Citation Formats


                    Ellis, Ross J., Reinhart, Benjamin, Williams, Neil J., Moyer, Bruce A., and Bryantsev, Vyacheslav S. Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole.  United States: N. p., 2017. 
Web.  doi:10.1039/C7CC02347B.

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                    Ellis, Ross J., Reinhart, Benjamin, Williams, Neil J., Moyer, Bruce A., & Bryantsev, Vyacheslav S. Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole.  United States.  https://doi.org/10.1039/C7CC02347B

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                    Ellis, Ross J., Reinhart, Benjamin, Williams, Neil J., Moyer, Bruce A., and Bryantsev, Vyacheslav S. Thu .  
"Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole".  United States.  https://doi.org/10.1039/C7CC02347B.  https://www.osti.gov/servlets/purl/1367215.

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@article{osti_1367215,

  title        = {Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole},

  author       = {Ellis, Ross J. and Reinhart, Benjamin and Williams, Neil J. and Moyer, Bruce A. and Bryantsev, Vyacheslav S.},

  abstractNote = {The role of solvent in molecular recognition systems is under-researched and often ignored, especially when the solvent is considered “non-interacting”. This study concerns the role of toluene solvent in cesium(I) recognition by calix[4]pyrrole. We show that π-donor interactions bind toluene molecules onto the open face of the cation-receptor complex, thus “capping the calix.” As a result, by characterizing this unusual aromatically-saturated complex, we show how “non-interacting” aromatic solvents can directly coordinate receptor-bound cations and thus influence recognition.},

  doi          = {10.1039/C7CC02347B},

  journal      = {ChemComm},

  number       = 41,

  volume       = 53,

  place        = {United States},

  year         = {Thu May 04 00:00:00 EDT 2017},

  month        = {Thu May 04 00:00:00 EDT 2017}

}

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Works referenced in this record:

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Works referencing / citing this record:

Molekulares Engineering freier Porphyrinbasen als Liganden - das N-H⋅⋅⋅X-Bindungsmotiv in Tetrapyrrolen
journal, November 2018

Kielmann, Marc; Senge, Mathias O.
Angewandte Chemie, Vol. 131, Issue 2
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Molecular Engineering of Free-Base Porphyrins as Ligands-The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles
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Wang, Jianlong; Zhuang, Shuting
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Probing the existence of uranyl trisulfate structures in the AMEX solvent extraction process
journal, January 2019

Sukhbaatar, Tamir; Duvail, Magali; Dumas, Thomas
Chemical Communications, Vol. 55, Issue 53
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Title: Capping the calix: How toluene completes cesium(i) coordination with calix[4]pyrrole

Abstract

Citation Formats

Calix[4]pyrrole-Based Ion Pair Receptors journal, June 2014

Tetra-phosphonate Calix[4]pyrrole Cavitands as Multitopic Receptors for the Recognition of Ion Pairs journal, January 2015

The Cation−π Interaction journal, June 2012

Ion vs. ion pair receptor: NMR and DFT study of the interaction of Thallium and Cesium ions and ion pairs with meso-octamethylcalix[4]pyrrole journal, May 2012

Conformational Features and Anion-Binding Properties of Calix[4]pyrrole: A Theoretical Study journal, June 2001

Ab initio energy-adjusted pseudopotentials for elements of groups 13–17 journal, December 1993

Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects journal, September 2006

Development and validation of COMPASS force field parameters for molecules with aliphatic azide chains journal, January 2003

Solvation Science: A New Interdisciplinary Field journal, December 2015

Nonlinear Optical Properties of Alkalides Li+(calix[4]pyrrole)M- (M = Li, Na, and K): Alkali Anion Atomic Number Dependence journal, January 2006

α,α′,α″,α′″- meso -tetrahexyltetramethyl-calix[4]pyrrole: an easy-to-prepare, isomerically pure anion extractant with enhanced solubility in organic solvents journal, October 2015

A colourimetric calix[4]pyrrole–4-nitrophenolate based anion sensor† journal, January 1999

Fast Parallel Algorithms for Short-Range Molecular Dynamics journal, March 1995

Quantitative Evaluation of Anion–π Interactions in Solution journal, May 2008

Drug Delivery with a Calixpyrrole– trans -Pt(II) Complex journal, February 2013

Halide anion recognition by calix[4]pyrrole: a quantum chemical study journal, April 2002

Investigation of cesium adsorption on soil and sediment samples from Fukushima Prefecture by sequential extraction and EXAFS technique journal, January 2012

A Multinuclear Solid-State NMR Study of Alkali Metal Ions in Tetraphenylborate Salts, M[BPh 4 ] (M = Na, K, Rb and Cs): What Is the NMR Signature of Cation−π Interactions? journal, October 2008

Calix[4]pyrrole: A New Ion-Pair Receptor As Demonstrated by Liquid−Liquid Extraction journal, March 2008

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals journal, July 2007

Long-range corrected double-hybrid density functionals journal, November 2009

Cation-π interaction of the univalent silver cation with meso-octamethylcalix[4]pyrrole: Experimental and theoretical study journal, February 2017

The Binding of Sulfate Anions by Guanidinium Receptors is Entropy-Driven journal, October 1998

Addressing Association Entropy by Reconstructing Guanidinium Anchor Groups for Anion Binding: Design, Synthesis, and Host–Guest Binding Studies in Polar and Protic Solutions journal, July 2008

Calix[4]pyrrole: An Old yet New Ion-Pair Receptor journal, April 2005

The accuracy of the pseudopotential approximation: non-frozen-core effects for spectroscopic constants of alkali fluorides XF (X = K, Rb, Cs) journal, June 1996

Interaction of the cesium cation with meso-octamethylcalix[4]pyrrole: Experimental and theoretical study journal, February 2017

EXAFS studies of cesium complexation by dibenzo-crown ethers in tri-n-butyl phosphate journal, February 1997

Behavior of Cesium and Thallium Cations inside a Calixarene Cavity As Probed by Nuclear Spin Relaxation. Evidence of Cation−π Interactions in Water journal, August 2009

Exploring the Dynamics of Calix[4]pyrrole: Effect of Solvent and Fluorine Substitution journal, January 2007

Calix[4]pyrrole: An Old yet New Ion-Pair Receptor journal, April 2005

Quantitative Evaluation of Anion–π Interactions in Solution journal, May 2008

Molekulares Engineering freier Porphyrinbasen als Liganden - das N-H⋅⋅⋅X-Bindungsmotiv in Tetrapyrrolen journal, November 2018

Molecular Engineering of Free-Base Porphyrins as Ligands-The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles journal, November 2018

Removal of cesium ions from aqueous solutions using various separation technologies journal, April 2019

Probing the existence of uranyl trisulfate structures in the AMEX solvent extraction process journal, January 2019

Calix[4]pyrrole-Based Ion Pair Receptors
journal, June 2014

Tetra-phosphonate Calix[4]pyrrole Cavitands as Multitopic Receptors for the Recognition of Ion Pairs
journal, January 2015

The Cation−π Interaction
journal, June 2012

Ion vs. ion pair receptor: NMR and DFT study of the interaction of Thallium and Cesium ions and ion pairs with meso-octamethylcalix[4]pyrrole
journal, May 2012

Conformational Features and Anion-Binding Properties of Calix[4]pyrrole: A Theoretical Study
journal, June 2001

Ab initio energy-adjusted pseudopotentials for elements of groups 13–17
journal, December 1993

Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects
journal, September 2006

Development and validation of COMPASS force field parameters for molecules with aliphatic azide chains
journal, January 2003

Solvation Science: A New Interdisciplinary Field
journal, December 2015

Nonlinear Optical Properties of Alkalides Li⁺(calix[4]pyrrole)M^- (M = Li, Na, and K): Alkali Anion Atomic Number Dependence
journal, January 2006

α,α′,α″,α′″- meso -tetrahexyltetramethyl-calix[4]pyrrole: an easy-to-prepare, isomerically pure anion extractant with enhanced solubility in organic solvents
journal, October 2015

A colourimetric calix[4]pyrrole–4-nitrophenolate based anion sensor†
journal, January 1999

Fast Parallel Algorithms for Short-Range Molecular Dynamics
journal, March 1995

Quantitative Evaluation of Anion–π Interactions in Solution
journal, May 2008

Drug Delivery with a Calixpyrrole– trans -Pt(II) Complex
journal, February 2013

Halide anion recognition by calix[4]pyrrole: a quantum chemical study
journal, April 2002

Investigation of cesium adsorption on soil and sediment samples from Fukushima Prefecture by sequential extraction and EXAFS technique
journal, January 2012

A Multinuclear Solid-State NMR Study of Alkali Metal Ions in Tetraphenylborate Salts, M[BPh ₄ ] (M = Na, K, Rb and Cs): What Is the NMR Signature of Cation−π Interactions?
journal, October 2008

Calix[4]pyrrole: A New Ion-Pair Receptor As Demonstrated by Liquid−Liquid Extraction
journal, March 2008

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007

Long-range corrected double-hybrid density functionals
journal, November 2009

Cation-π interaction of the univalent silver cation with meso-octamethylcalix[4]pyrrole: Experimental and theoretical study
journal, February 2017

The Binding of Sulfate Anions by Guanidinium Receptors is Entropy-Driven
journal, October 1998

Addressing Association Entropy by Reconstructing Guanidinium Anchor Groups for Anion Binding: Design, Synthesis, and Host–Guest Binding Studies in Polar and Protic Solutions
journal, July 2008

Calix[4]pyrrole: An Old yet New Ion-Pair Receptor
journal, April 2005

The accuracy of the pseudopotential approximation: non-frozen-core effects for spectroscopic constants of alkali fluorides XF (X = K, Rb, Cs)
journal, June 1996

Interaction of the cesium cation with meso-octamethylcalix[4]pyrrole: Experimental and theoretical study
journal, February 2017

EXAFS studies of cesium complexation by dibenzo-crown ethers in tri-n-butyl phosphate
journal, February 1997

Behavior of Cesium and Thallium Cations inside a Calixarene Cavity As Probed by Nuclear Spin Relaxation. Evidence of Cation−π Interactions in Water
journal, August 2009

Exploring the Dynamics of Calix[4]pyrrole: Effect of Solvent and Fluorine Substitution
journal, January 2007

Calix[4]pyrrole: An Old yet New Ion-Pair Receptor
journal, April 2005

Quantitative Evaluation of Anion–π Interactions in Solution
journal, May 2008

Molekulares Engineering freier Porphyrinbasen als Liganden - das N-H⋅⋅⋅X-Bindungsmotiv in Tetrapyrrolen
journal, November 2018

Molecular Engineering of Free-Base Porphyrins as Ligands-The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles
journal, November 2018

Removal of cesium ions from aqueous solutions using various separation technologies
journal, April 2019

Probing the existence of uranyl trisulfate structures in the AMEX solvent extraction process
journal, January 2019