Effects of halogen and hydrogen bonding on defect disorder: the ladder that wasn't there

Abdalrahman, Mahmoud A.; Awwadi, Firas F.; Jameson, Geoffrey B.; Landee, Christopher P.; Saunders, Christopher G.; Turnbull, Mark M.; Wikaira, Jan L.

doi:10.1039/c3ce40444g

Cited by 18 publications

(9 citation statements)

References 36 publications

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“…Although diamagnetism was observed in the diiodotetrathiafulvalene–ClO 4 and (diiodotetrathiafulvalene) 2 –2,6-naphthalenebis(sulfonate) materials, the assemblies of diiodotetrathiafulvalene with racemic camphor sulfonate, 1,5-naphthalenebis(sulfonate), and 2,6-anthracenebis(sulfonate) exhibited semiconducting behavior. XB interactions have also been explored in the development of ferromagnetic and antiferromagnetic materials.…”

Section: Halogen Bonding In the Solid Statementioning

confidence: 99%

Halogen Bonding in Supramolecular Chemistry

et al. 2015

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CONTENTS 1. Introduction to Halogen Bonding 7119 1.1. Nature of the Halogen Bond 7119 1.2. Scope of the Review 7120 2. Computational and Theoretical Investigations of Halogen Bonding 7120 2.1.Quantum Mechanics Methods 7120 2.2. σ-Hole Model of Halogen Bonding 7120 2.3. Other Contributions to the Nature of Halogen Bonding 7122 2.4. Recent Examples of Computationally Investigated Halogen-Bonded Complexes 7123 2.4.1. XB to Neutral Species 7123 2.4.2. XB to Anions 7126 2.4.3. XB in Protein−Ligand Complexes 7127 2.4.4. Electron-Transfer Processes Affected by XB Interactions 7127 2.5. Classical Force Field Calculations 7127 2.6. Conclusions and Outlook 7129 3. Gas-Phase Studies of Halogen-Bonding Interactions 7130 4. Halogen Bonding in the Solid State 7131 4.1. Introduction to Crystal Engineering and Functional Materials 7131 4.2. Fundamentals 7132 4.3. Halogen-Bonding Hierarchy 7134 4.3.1. Ranking Halogen-Bond Donors 7134 4.3.2. HB/XB Complementarity/Competition 7136 4.3.3. Predicting XBs 7138 4.4. Control of Solid-State Supramolecular Architectures 7138 4.4.1. Polymorphism 7138 4.4.2. Stoichiometry 7139 4.4.3. Tautomeric Control 7140 4.4.4. XBs Involving Metals and Metal-Bound XBs 7140 4.4.5. XB with Anions in the Solid State 4.5. Solid-State Architectures 4.6.

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Section: Halogen Bonding In the Solid Statementioning

confidence: 99%

Halogen Bonding in Supramolecular Chemistry

et al. 2015

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“…Copper(II) in distorted square-pyramidal coordination of chloride and oxygen atoms wasalso reported as anionic polymer strand in several compounds for a [Cu II O 2 Cl 3 ] coordination environment [70] and in [Cu(C 2 H 7 N 5 ) 2 ][Cu(C 5 H 7 O 2 ) 2 Cl] 2 [71] for [Cu II [72] and [Cu(C 18 H 34 O 4 N 2 )Cl 2 ] (194.0 pm and 228.5 pm). [73] Similar to the compound reported herein, only minor deviations from 90°cis and 180°trans angles appear.…”

Section: [Cu 3 (Bet) 4 CL 3 ][Ntfmentioning

confidence: 99%

Speciation of Copper(II)‐Betaine Complexes as Starting Point for Electrochemical Copper Deposition from Ionic Liquids

2020

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The application of ionic liquids for the dissolution of metal oxides is a promising field for the development of more energy‐ and resource‐efficient metallurgical processes. Using such solutions for the production of valuable chemicals or electrochemical metal deposition requires a detailed understanding of the chemical system and the factors influencing it. In the present work, several compounds are reported that crystallize after the dissolution of copper(II) oxide in the ionic liquid [Hbet][NTf2]. Dependent on the initial amount of chloride, the reaction temperature and the purity of the reagent, copper crystallizes in complexes with varying coordination geometries and ligands. Subsequently, the influence of these different complex species on electrochemical properties is shown. For the first time, copper is deposited from the ionic liquid [Hbet][NTf2], giving promising opportunities for more resource‐efficient copper plating. The copper coatings were analyzed by SEM and EDX measurements. Furthermore, a mechanism for the decomposition of [Hbet][NTf2] in the presence of chloride is suggested and supported by experimental evidence.

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“…d I ⋅⋅⋅ Cl− =3.33(9) Å). The XB distances in [ RuArI ]Cl and [ RuArI ]Cl⋅MeOH are more comparable to the ArI⋅⋅⋅Cl − contacts observed in the salts of iodopyridinium [12, 38–40] and N ‐alkyl‐iodopyridinium [10, 36, 41–43] cations (avg. d I⋅⋅⋅Cl− =3.23(11) Å), species which are widely recognized to be strong XB donors.…”

Section: Resultsmentioning

confidence: 66%

“Click”‐Like η⁶‐Metalation/Demetalation of Aryl Iodides as a Means of Turning “ON/OFF” Halogen Bond Donor Functionality

Kelly

Holman

2022

Angewandte Chemie

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η6‐Metalated aryl halides are recognized as a class of halogen bond (XB) donors. Click‐like η6‐metalation/demetalation of aryl iodides by cyclopentadienylruthenium(II) ([CpRuII]+) is shown to turn ON/OFF (amplify/suppress) XB donor functionality. [CpRu(MeCN)3][PF6] is shown to react quantitatively with iodobenzenes (ArIn, n=1,2) to yield [CpRu(η6‐ArIn)][PF6] compounds. Photochemical demetalation (405 nm) quantitatively reverts these compounds to ArIn and [CpRu(MeCN)3][PF6]. Crystal structures of [CpRu(ArXn)]+ salts show that the [CpRu(ArIn)]+ cations are strong, charge‐assisted XB donors analogous to iodopyridinium cations. XB‐induced association of [CpRu(C6H5I)]+ with diazobicyclo[2.2.2]octane (DABCO) is established by NMR spectroscopy. [CpRu(C6H5I)][BPh4] and [CpRu(1,4‐C6H4I2)][BPh4] co‐crystallize with DABCO and the structure of [CpRu(1,4‐C6H4I2)][BPh4]⋅DABCO⋅Et2O is reported. DFT calculations support amplification of the XBing capabilities of aryl iodides upon [CpRu]+‐metalation.

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Effects of halogen and hydrogen bonding on defect disorder: the ladder that wasn't there

Cited by 18 publications

References 36 publications

Halogen Bonding in Supramolecular Chemistry

Halogen Bonding in Supramolecular Chemistry

Speciation of Copper(II)‐Betaine Complexes as Starting Point for Electrochemical Copper Deposition from Ionic Liquids

“Click”‐Like η⁶‐Metalation/Demetalation of Aryl Iodides as a Means of Turning “ON/OFF” Halogen Bond Donor Functionality

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Effects of halogen and hydrogen bonding on defect disorder: the ladder that wasn't there

Cited by 18 publications

References 36 publications

Halogen Bonding in Supramolecular Chemistry

Halogen Bonding in Supramolecular Chemistry

Speciation of Copper(II)‐Betaine Complexes as Starting Point for Electrochemical Copper Deposition from Ionic Liquids

“Click”‐Like η6‐Metalation/Demetalation of Aryl Iodides as a Means of Turning “ON/OFF” Halogen Bond Donor Functionality

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“Click”‐Like η⁶‐Metalation/Demetalation of Aryl Iodides as a Means of Turning “ON/OFF” Halogen Bond Donor Functionality