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Title: Anion-Binding Macrocycles Operate Beyond the Electrostatic Regime: Interaction Distances Matter

Abstract

Not provided.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [3]
  1. Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue Bloomington Indiana 47405 USA; Current Address: Department of Chemistry, Michigan State University, East Lansing Michigan 48824 USA
  2. Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue Bloomington Indiana 47405 USA; Current Address: Beckman Institute for Advanced Science and Technology, University of Illinois at Urbana-Champaign, Urbana Illinois 61801 USA
  3. Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue Bloomington Indiana 47405 USA
Publication Date:
Research Org.:
Indiana Univ., Bloomington, IN (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1537525
DOE Contract Number:  
SC0002728
Resource Type:
Journal Article
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 24; Journal Issue: 54; Journal ID: ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
Chemistry

Citation Formats

Sengupta, Arkajyoti, Liu, Yun, Flood, Amar H., and Raghavachari, Krishnan. Anion-Binding Macrocycles Operate Beyond the Electrostatic Regime: Interaction Distances Matter. United States: N. p., 2018. Web. doi:10.1002/chem.201802657.
Sengupta, Arkajyoti, Liu, Yun, Flood, Amar H., & Raghavachari, Krishnan. Anion-Binding Macrocycles Operate Beyond the Electrostatic Regime: Interaction Distances Matter. United States. https://doi.org/10.1002/chem.201802657
Sengupta, Arkajyoti, Liu, Yun, Flood, Amar H., and Raghavachari, Krishnan. Wed . "Anion-Binding Macrocycles Operate Beyond the Electrostatic Regime: Interaction Distances Matter". United States. https://doi.org/10.1002/chem.201802657.
@article{osti_1537525,
title = {Anion-Binding Macrocycles Operate Beyond the Electrostatic Regime: Interaction Distances Matter},
author = {Sengupta, Arkajyoti and Liu, Yun and Flood, Amar H. and Raghavachari, Krishnan},
abstractNote = {Not provided.},
doi = {10.1002/chem.201802657},
url = {https://www.osti.gov/biblio/1537525}, journal = {Chemistry - A European Journal},
issn = {0947-6539},
number = 54,
volume = 24,
place = {United States},
year = {2018},
month = {9}
}

Works referenced in this record:

Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications
journal, September 2014


Supramolekulare Chemie von Anionen: von der Erkennung zur chemischen Anwendung
journal, September 2014


Applications of Supramolecular Anion Recognition
journal, May 2015


Anion Receptor Chemistry
journal, September 2016


Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective
journal, November 2015


Anionenerkennung in Wasser: aktuelle Fortschritte aus supramolekularer und makromolarer Sicht
journal, November 2015


Anion Recognition in Aqueous Media by Cyclopeptides and Other Synthetic Receptors
journal, October 2017


Anion Recognition Strategies Based on Combined Noncovalent Interactions
journal, June 2017


Supramolecular Chemistry of Anionic Dimers, Trimers, Tetramers, and Clusters
journal, January 2018


Synthetic ion transporters can induce apoptosis by facilitating chloride anion transport into cells
journal, August 2014


A Synthetic Supramolecular Receptor for the Hydrosulfide Anion
journal, August 2016


A Synthetic Supramolecular Receptor for the Hydrosulfide Anion
journal, August 2016


Anion-π Enzymes
journal, April 2016


A synthetic ion transporter that disrupts autophagy and induces apoptosis by perturbing cellular chloride concentrations
journal, January 2017


Anion Recognition as a Supramolecular Switch of Cell Internalization
journal, December 2016


99 TcO 4 : Selective Recognition and Trapping in Aqueous Solution
journal, August 2012


99 TcO 4 : Selective Recognition and Trapping in Aqueous Solution
journal, August 2012


Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion
journal, October 2014


Hemispherand-Strapped Calix[4]pyrrole: An Ion-pair Receptor for the Recognition and Extraction of Lithium Nitrite
journal, August 2016


Ion-Mediated Electron Transfer in a Supramolecular Donor-Acceptor Ensemble
journal, September 2010


High-Fidelity Multistate Switching with Anion-Anion and Acid-Anion Dimers of Organophosphates in Cyanostar Complexes
journal, September 2017


High-Fidelity Multistate Switching with Anion-Anion and Acid-Anion Dimers of Organophosphates in Cyanostar Complexes
journal, September 2017


Chiral Triazoles in Anion-Binding Catalysis: New Entry to Enantioselective Reissert-Type Reactions
journal, January 2016


Exploiting non-covalent π interactions for catalyst design
journal, March 2017


Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions
journal, January 2017


A data-intensive approach to mechanistic elucidation applied to chiral anion catalysis
journal, February 2015


Cinchona Alkaloid-Catalyzed Asymmetric Conjugate Additions: The Bifunctional Brønsted Acid–Hydrogen Bonding Model
journal, January 2016


Structural Criteria for the Design of Anion Receptors:  The Interaction of Halides with Electron-Deficient Arenes
journal, January 2007


Solution Phase Measurement of Both Weak σ and C−H···X Hydrogen Bonding Interactions in Synthetic Anion Receptors
journal, August 2008


Strong CH⋅⋅⋅Halide Hydrogen Bonds from 1,2,3-Triazoles Quantified Using Pre-Organized and Shape-Persistent Triazolophanes
journal, October 2009


A Pyrrolyl-Based Triazolophane: A Macrocyclic Receptor With CH and NH Donor Groups That Exhibits a Preference for Pyrophosphate Anions
journal, October 2010


Aromatic and Aliphatic CH Hydrogen Bonds Fight for Chloride while Competing Alongside Ion Pairing within Triazolophanes
journal, November 2010


From Atomic to Molecular Anions: A Neutral Receptor Captures Cyanide Using Strong CH Hydrogen Bonds
journal, June 2011


Capture and metathesis-based release of potassium salts by a multitopic ion receptor
journal, January 2013


Hydrophobic Collapse of Foldamer Capsules Drives Picomolar-Level Chloride Binding in Aqueous Acetonitrile Solutions
journal, September 2013


An Overlooked yet Ubiquitous Fluoride Congenitor: Binding Bifluoride in Triazolophanes Using Computer-Aided Design
journal, March 2014


C vs N: Which End of the Cyanide Anion Is a Better Hydrogen Bond Acceptor?
journal, April 2014


Substituent Effects in CH Hydrogen Bond Interactions: Linear Free Energy Relationships and Influence of Anions
journal, November 2015


Anionic CH⋅⋅⋅X Hydrogen Bonds: Origin of Their Strength, Geometry, and Other Properties
journal, November 2014


Flexibility Coexists with Shape-Persistence in Cyanostar Macrocycles
journal, March 2016


Anions Stabilize Each Other inside Macrocyclic Hosts
journal, October 2016


Anions Stabilize Each Other inside Macrocyclic Hosts
journal, October 2016


Assembly of Effective Halide Receptors from Components. Comparing Hydrogen, Halogen, and Tetrel Bonds
journal, April 2017


Anion Binding in Solution: Beyond the Electrostatic Regime
journal, September 2017


Calixphyrins. Hybrid macrocycles at the structural crossroads between porphyrins and calixpyrroles
journal, July 2001


Second Generation Calixpyrrole Anion Sensors
journal, September 2000


Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry: Calix[4]pyrrole-Based Anion Receptor Chemistry
journal, March 2015


Pure CH Hydrogen Bonding to Chloride Ions: A Preorganized and Rigid Macrocyclic Receptor
journal, March 2008


Pure CH Hydrogen Bonding to Chloride Ions: A Preorganized and Rigid Macrocyclic Receptor
journal, March 2008


Are C−H Groups Significant Hydrogen Bonding Sites in Anion Receptors? Benzene Complexes with Cl - , NO 3 - , and ClO 4 -
journal, June 2005


Influence of Substituents on the Strength of Aryl C−H···Anion Hydrogen Bonds
journal, October 2005


Helicity Inversion in Responsive Foldamers Induced by Achiral Halide ion Guests
journal, June 2008


Helixinversion in responsiven Foldameren durch achirale Gastmoleküle (Halogenidionen)
journal, June 2008


Preorganized Aryltriazole Foldamers as Effective Transmembrane Transporters for Chloride Anion
journal, July 2014


A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes
journal, June 2013


Potential Energy Curves for Cation−π Interactions: Off-Axis Configurations Are Also Attractive
journal, December 2009


Structures of protonated benzene dimer and intermolecular interaction decomposition via symmetry-adapted perturbation theory
journal, October 2011


Buckyplates and Buckybowls: Examining the Effects of Curvature on π–π Interactions
journal, November 2012


Energy Component Analysis of π Interactions
journal, June 2012


Levels of symmetry adapted perturbation theory (SAPT). I. Efficiency and performance for interaction energies
journal, March 2014


Noncovalent π⋅⋅⋅π interaction between graphene and aromatic molecule: Structure, energy, and nature
journal, March 2014


Accurate, Precise, and Efficient Theoretical Methods To Calculate Anion−π Interaction Energies in Model Structures
journal, December 2014


Quantifying the π-Stacking Interactions in Nitroarene Binding Sites of Proteins
journal, November 2015


Can Dispersion Forces Govern Aromatic Stacking in an Organic Solvent?
journal, December 2015


Can Dispersion Forces Govern Aromatic Stacking in an Organic Solvent?
journal, December 2015


Is Electrostatics Sufficient to Describe Hydrogen-Bonding Interactions?
journal, January 2014


Nature of Hydrogen Bonding in Charged Hydrogen-Bonded Complexes and Imidazolium-Based Ionic Liquids
journal, December 2011


Electron Density Characteristics in Bond Critical Point (QTAIM) versus Interaction Energy Components (SAPT): The Case of Charge-Assisted Hydrogen Bonding
journal, December 2011


Magnitude and Mechanism of Charge Enhancement of CH··O Hydrogen Bonds
journal, September 2013


Perturbation Theory Approach to Intermolecular Potential Energy Surfaces of van der Waals Complexes
journal, November 1994


Symmetry-adapted perturbation theory of intermolecular forces: Symmetry-adapted perturbation theory
journal, August 2011


Wavefunction methods for noncovalent interactions: Noncovalent interactions
journal, July 2011

  • Hohenstein, Edward G.; Sherrill, C. David
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 2
  • https://doi.org/10.1002/wcms.84

Energy decomposition analysis approaches and their evaluation on prototypical protein–drug interaction patterns
journal, January 2015


From Helix to Macrocycle: Anion-Driven Conformation Control of π-Conjugated Acyclic Oligopyrroles
journal, December 2010


Two distinct anion-binding modes and their relative stabilities
journal, January 2007


Synthesis and Anion Binding Properties of 2,5-Diamidothiophene Polypyrrole Schiff Base Macrocycles
journal, November 2005


Dispersive Interactions in Solution Complexes
journal, June 2015


Quantifying Intermolecular Interactions: Guidelines for the Molecular Recognition Toolbox
journal, October 2004


Zwischenmolekulare Wechselwirkungen in Lösung: eine vereinfachende Quantifizierungsmethode
journal, October 2004


Gaussian basis sets for use in correlated molecular calculations. IV. Calculation of static electrical response properties
journal, February 1994


Integration Grid Errors for Meta-GGA-Predicted Reaction Energies: Origin of Grid Errors for the M06 Suite of Functionals
journal, January 2010


Basis-set convergence in correlated calculations on Ne, N2, and H2O
journal, April 1998


The ORCA program system: The ORCA program system
journal, June 2011


Psi4: an open-source ab initio electronic structure program : Psi4: an electronic structure program
journal, October 2011

  • Turney, Justin M.; Simmonett, Andrew C.; Parrish, Robert M.
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 4
  • https://doi.org/10.1002/wcms.93

Perspectives on Basis Sets Beautiful: Seasonal Plantings of Diffuse Basis Functions
journal, August 2011


Extrapolation and Scaling of the DFT-SAPT Interaction Energies toward the Basis Set Limit
journal, February 2011