4.6 Article

Intrinsic bond strength index as a halogen bond interaction energy predictor

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Independent gradient model based on Hirshfeld partition: A new method for visual study of interactions in chemical systems

Tian Lu et al.

Summary: The powerful independent gradient model (IGM) method has limitations in graphically studying weak interactions. In this article, an improved version of IGM, called IGM based on Hirshfeld partition (IGMH), is proposed to overcome the shortcomings. The rigorous physical background of IGMH is demonstrated through various application examples, showcasing its important value in intuitively understanding interactions in chemical systems.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2022)

Article Chemistry, Organic

Evaluation of 6-Halogenated 2-Pyridone Moieties as Halogen Bond Donors

Martin H. H. Voelkel et al.

Summary: In this study, the halogen bonding properties of 6-halo-2-pyridones and their pyridol tautomers were investigated both in the solid state and in solution. The results showed that halogen bonding indeed played a role in the packing motif in pyridone crystals, while no clear evidence for halogen bonding was found in solution.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Meta-Hybrid Density Functional Theory Prediction of the Reactivity, Stability, and IGM of Azepane, Oxepane, Thiepane, and Halogenated Cycloheptane

Tomsmith O. Unimuke et al.

Summary: The application of plain cycloalkanes and heterocyclic derivatives in the synthesis of valuable natural products and pharmacologically active intermediates has increased significantly in recent times, with a focus on lower cycloalkane members. The structural and molecular properties of higher seven-membered and nonaromatic heterocyclic derivatives are less understood, despite their stable nature and extensive application, indicating a need for further research in this area. Various quantum chemical calculations were employed to investigate the structural reactivity, stability, and behavior of substituents on cycloheptane and its derivatives, revealing insights into their molecular properties and interactions.

ACS OMEGA (2022)

Article Materials Science, Multidisciplinary

Achieving halogen bonding enhanced ultra-highly efficient AIE and reversible mechanochromism properties of TPE-based luminogens: position of bromine substituents

Xinrui Miao et al.

Summary: This study systematically investigated the impact of introducing phenyl and bromine substituents on AIE materials, and found that different positions of bromine substituents can lead to diverse intermolecular interactions, with intermolecular Br-Br bonds playing a dominant role in fluorescence efficiency. Furthermore, a comprehensive exploration of MC and AIE properties contributes to the development of materials with higher luminous efficiency.

JOURNAL OF MATERIALS CHEMISTRY C (2022)

Review Chemistry, Multidisciplinary

Noncovalent interactions in proteins and nucleic acids: beyond hydrogen bonding and π-stacking

Subhrakant Jena et al.

Summary: This article discusses the significant relevance of noncovalent interactions (NCIs) in biomolecular structure and function, such as hydrogen bonding, halogen bonding, and the more recently discovered n→π* interactions. These interactions are crucial for understanding the dynamics of biological systems, enzymatic activities, and drug design.

CHEMICAL SOCIETY REVIEWS (2022)

Article Chemistry, Multidisciplinary

Calix[6]arenes with halogen bond donor groups as selective and efficient anion transporters

Anurag Singh et al.

Summary: This study demonstrates the anion binding and anion transport properties of a series of calix[6]arenes decorated with halogen bond or hydrogen bond donating groups on their small rim. The results show that the halogen bond donating iodotriazole groups enable highly selective transport of chloride and nitrate anions, without the transport of protons or hydroxide.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

An emerging deep eutectic solvent based on halogen-bonds

Ruifen Shi et al.

Summary: A new deep eutectic solvent (DES) driven by halogen bonding (XB) has been developed, forming a family of eutectic mixtures in the liquid state through the combination of quaternary ammonium salts and dihalogens. The study not only broadens the potential applications of DES systems but also reveals the potential of XB complexes as solvents.

CHEMICAL COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

Halogen Bonding Involving Palladium(II) as an XB Acceptor

Eugene A. Katlenok et al.

Summary: This study investigated the crystal structures of Pd-2(II) half-lantern complexes and cocrystals through X-ray crystallography, revealing the significant roles played by various noncovalent interactions such as I···Pd and I···E.

CRYSTAL GROWTH & DESIGN (2021)

Article Chemistry, Multidisciplinary

The use and misuse of van der Waals radii

Peter Politzer et al.

Summary: The relationship between van der Waals radii and noncovalent interactions is not absolute, requiring caution. The uncertainty in the values of van der Waals radii may lead to missed interactions, and sometimes interactions do not occur between atoms.

STRUCTURAL CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Halogen Bonding: An Underestimated Player in Membrane-Ligand Interactions

Rafael Santana Nunes et al.

Summary: Halogen bonds (XBs) are noncovalent interactions in which halogen atoms act as electrophilic species interacting with Lewis bases. This type of interaction is relevant in biological membrane systems, influencing the pharmacological or toxicological activity of halogenated compounds. Molecular dynamics simulations provide evidence of the effects of XBs on ligands' membrane insertion profile and orientational preferences.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Physical

Can Counter-Intuitive Halogen Bonding Be Coulombic?

Jane S. Murray et al.

Summary: In this study, counter-intuitive halogen bonding with nitrogen bases is discussed, showing that despite apparent repulsion between ground-state molecules, these interactions can be treated as Coulombic when considering both electrostatics and polarization. The energies of various interactions can be well described using just two molecular properties: the electrostatic potential of the halogen sigma-hole and the average polarizability of the nitrogen base. Moreover, these properties can also represent an expanded data base that includes various types of halogen bonding interactions.

CHEMPHYSCHEM (2021)

Article Chemistry, Physical

Role of Charge Transfer in Halogen Bonding

Brandon Inscoe et al.

Summary: This study investigates the impact of charge transfer effects on geometries, spectral properties, and energetics in halogen bonding complexes, showing that charge transfer interaction significantly shortens the X···Z bonding distance and stretches the C-X bonds. However, the shortening of the halogen bonding results in less favorable steric effects. There are approximate linear correlations between the charge transfer effect and binding energy, and between bonding distance and binding energy.

JOURNAL OF PHYSICAL CHEMISTRY A (2021)

Article Biochemistry & Molecular Biology

Strength of the [Z-I•••Hal]- and [Z-Hal•••I]- Halogen Bonds: Electron Density Properties and Halogen Bond Length as Estimators of Interaction Energy

Maxim L. Kuznetsov

Summary: This study established important relationships between interaction energy and electron density, its Laplacian, curvature, potential, kinetic, and total energy densities at the bond critical point as well as bond length for structures involving halogen bonds with iodine as the interacting atom. The mean absolute deviations for the correlations found ranged from 2.06 to 4.76 kcal/mol.

MOLECULES (2021)

Article Chemistry, Multidisciplinary

Halogen Bonding Mediated Hierarchical Supramolecular Chirality

Shuguo An et al.

Summary: This study successfully manipulated supramolecular chirality in hierarchically self-assembled systems via halogen bonds, unveiling the potential of halogen bonds in constructing functional chiroptical materials.

ACS NANO (2021)

Review Chemistry, Organic

Halides as versatile anions in asymmetric anion-binding organocatalysis

Lukas Schifferer et al.

Summary: This review provides an overview of the role of halide anions in asymmetric anion-binding organocatalysis. It highlights the use of halides in the catalyst-anion complex as either a mere counter-anion spectator or an active nucleophile, and discusses new trends towards additional noncovalent contacts involving HB-donor catalysts and supramolecular interactions with anions and cationic reactive species.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Anti-electrostatic Halogen Bonding between Ions of Like Charge

Jana M. Holthoff et al.

Summary: Halogen bonding, a predominantly electrostatic interaction between molecules featuring Lewis acidic halogen substituents and Lewis bases, may seem counter-intuitive when considering interactions between ions of like charge. The overview includes theoretical studies, experimental evidences in crystals and solution, comparisons with other types of adducts, and comments on key differences between charge-transfer and electrostatic polarization.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Physical

Proximity Effects of Substituents on Halogen Bond Strength

Jordan Lapp et al.

Summary: The study investigates the effects of electron-withdrawing substituents (EWS) on halogen bond (XB) properties, finding that increasing the number of triple bonds in alkynes enhances the strength of XB, while elongating alkene chains has minimal impact and the cyano group has a stronger effect than fluorine. In aromatic iodobenzene, it is observed that the effects of EWS diminish with distance, with EWS on the phenyl ring exhibiting the strongest effect and disubstitution having nearly additive effects.

JOURNAL OF PHYSICAL CHEMISTRY A (2021)

Article Chemistry, Physical

Probing Interfacial Halogen-Bonding Effects with Halogenated Organic Dyes and a Lewis Base-Decorated Transition Metal-Based Redox Shuttle at a Metal Oxide Interface in Dye-Sensitized Solar Cells

Christine Curiac et al.

Summary: This study found that metal-free molecular sensitizers with halogen decorations may form halogen bonding with a halogen-binding RS, leading to significant impacts on electron transfer reaction rates.

JOURNAL OF PHYSICAL CHEMISTRY C (2021)

Article Chemistry, Medicinal

Structurally Optimized Potent Dual-Targeting NBTI Antibacterials with an Enhanced Bifurcated Halogen-Bonding Propensity

Maja Kokot et al.

Summary: The study focused on designing and synthesizing novel bacterial topoisomerase inhibitors with enhanced potency through halogen bonding. The inhibitors showed strong antibacterial activity against Staphylococcus aureus, but were less effective against Escherichia coli and other Gram-negative pathogens due to their high substrate specificity for bacterial efflux pumps.

ACS MEDICINAL CHEMISTRY LETTERS (2021)

Article Chemistry, Organic

Halogen bonding effect on electrochemical anion oxidation in ionic liquids

Marie Stacey Alvarez et al.

Summary: Three imidazolium-based ionic liquids were compared as solvents for the oxidation of various anions. The study revealed the crucial role of non-covalent halogen bonding in determining the oxidation potentials and electrochemical window of the ILs.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Crystal Engineering with Multipoint Halogen Bonding: Double Two-Point Donors and Acceptors at Work

David Bulfield et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Bidentate Chiral Bis(imidazolium)-Based Halogen-Bond Donors: Synthesis and Applications in Enantioselective Recognition and Catalysis

Revannath L. Sutar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Is There a Single Ideal Parameter for Halogen-Bonding-Based Lewis Acidity?

Elric Engelage et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Medicinal

Halogen Bonds in Ligand-Protein Systems: Molecular Orbital Theory for Drug Design

Enrico Margiotta et al.

JOURNAL OF CHEMICAL INFORMATION AND MODELING (2020)

Article Chemistry, Physical

New Way for Probing Bond Strength

Johanna Klein et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2020)

Review Biochemistry & Molecular Biology

Application of Halogen Bonding to Organocatalysis: A Theoretical Perspective

Hui Yang et al.

MOLECULES (2020)

Article Multidisciplinary Sciences

A robust and tunable halogen bond organocatalyzed 2-deoxyglycosylation involving quantum tunneling

Chunfa Xu et al.

NATURE COMMUNICATIONS (2020)

Review Chemistry, Multidisciplinary

Supramolecular Halogen Bonds in Asymmetric Catalysis

Mikk Kaasik et al.

FRONTIERS IN CHEMISTRY (2020)

Article Chemistry, Inorganic & Nuclear

Novel approach to accurately predict bond strength and ligand lability in platinum-based anticancer drugs

Miguel Ponce-Vargas et al.

DALTON TRANSACTIONS (2020)

Article Chemistry, Multidisciplinary

The Halogen Bond: An Emerging Supramolecular Tool in the Design of Functional Mesomorphic Materials

Hao Wang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Multidisciplinary Sciences

Halogen bonding as a supramolecular dynamics catalyst

Patrick M. J. Szell et al.

NATURE COMMUNICATIONS (2019)

Review Pharmacology & Pharmacy

Halogen bonding in halocarbon-protein complexes and computational tools for rational drug design

Paulo J. Costa et al.

EXPERT OPINION ON DRUG DISCOVERY (2019)

Article Biochemistry & Molecular Biology

Electrostatics and polarization determine the strength of the halogen bond: a red card for charge transfer

Tore Brinck et al.

JOURNAL OF MOLECULAR MODELING (2019)

Article Chemistry, Inorganic & Nuclear

A Simple Model for Halogen Bond Interaction Energies

Robert A. Shaw et al.

INORGANICS (2019)

Article Chemistry, Physical

Halogen Bonding Interactions: Revised Benchmarks and a New Assessment of Exchange vs Dispersion

Lindsey N. Anderson et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2018)

Article Chemistry, Physical

The σ-Hole Coulombic Interpretation of Trihalide Anion Formation

Timothy Clark et al.

CHEMPHYSCHEM (2018)

Review Statistics & Probability

Minimum covariance determinant and extensions

Mia Hubert et al.

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL STATISTICS (2018)

Article Chemistry, Physical

Strength, character, and directionality of halogen bonds involving cationic halogen bond donors

Kevin E. Riley et al.

FARADAY DISCUSSIONS (2017)

Article Chemistry, Physical

On the role of charge transfer in halogen bonding

Jan Rezac et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2017)

Article Chemistry, Physical

Strength, character, and directionality of halogen bonds involving cationic halogen bond donors

Kevin E. Riley et al.

FARADAY DISCUSSIONS (2017)

Article Biochemistry & Molecular Biology

Structure-Energy Relationships of Halogen Bonds in Proteins

Matthew R. Scholfield et al.

BIOCHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Ion-Pair Halogen Bonds in 2-Halo-Functionalized Imidazolium Chloride Receptors: Substituent and Solvent Effects

Rafael Nunes et al.

CHEMISTRY-AN ASIAN JOURNAL (2017)

Review Chemistry, Multidisciplinary

Computer Modeling of Halogen Bonds and Other σ-Hole Interactions

Michal H. Kolar et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

The Halogen Bond

Gabriella Cavallo et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

Sequential Halogen Bonding with Ditopic Donors: σ-Hole Evolutions upon Halogen Bond Formation

Irene Nicolas et al.

CRYSTAL GROWTH & DESIGN (2016)

Article Chemistry, Physical

Halogen Bonding with Phosphine: Evidence for Mulliken Inner Complexes and the Importance of Relaxation Energy

Robert A. Shaw et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2016)

Article Chemistry, Physical

Local Electron Attachment Energy and Its Use for Predicting Nucleophilic Reactions and Halogen Bonding

Tore Brinck et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2016)

Article Chemistry, Physical

The intrinsic strength of the halogen bond: electrostatic and covalent contributions described by coupled cluster theory

Vytor Oliveira et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2016)

Article Multidisciplinary Sciences

Ultrastructural Characterization of the Lower Motor System in a Mouse Model of Krabbe Disease

Valentina Cappello et al.

SCIENTIFIC REPORTS (2016)

Article Chemistry, Multidisciplinary

Does Fluorine Participate in Halogen Bonding?

Kiamars Eskandari et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Article Chemistry, Multidisciplinary

Cationic Multidentate Halogen-Bond Donors in Halide Abstraction Organocatalysis: Catalyst Optimization by Preorganization

Stefan H. Jungbauer et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Physical

Halogen Bonding from Dispersion-Corrected Density-Functional Theory: The Role of De localization Error

A. Otero-de-la-Roza et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2014)

Article Chemistry, Physical

The halogen bond in thiirane ... ClF: an example of a Mulliken inner complex

J. Grant Hill

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2014)

Review Chemistry, Multidisciplinary

The Halogen Bond in the Design of Functional Supramolecular Materials: Recent Advances

Arri Priimagi et al.

ACCOUNTS OF CHEMICAL RESEARCH (2013)

Article Chemistry, Physical

Halogen Bonds: Benchmarks and Theoretical Analysis

Sebastian Kozuch et al.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2013)

Article Chemistry, Multidisciplinary

Definition of the halogen bond (IUPAC Recommendations 2013)

Gautam R. Desiraju et al.

PURE AND APPLIED CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Unexpected trends in halogen-bond based noncovalent adducts

Stefan M. Huber et al.

CHEMICAL COMMUNICATIONS (2012)

Article Chemistry, Multidisciplinary

Multiwfn: A multifunctional wavefunction analyzer

Tian Lu et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2012)

Article Chemistry, Physical

Property-optimized Gaussian basis sets for molecular response calculations

Dmitrij Rappoport et al.

JOURNAL OF CHEMICAL PHYSICS (2010)

Article Chemistry, Multidisciplinary

Revealing Noncovalent Interactions

Erin R. Johnson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Physical

Halogen bonding: an electrostatically-driven highly directional noncovalent interaction

Peter Politzer et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2010)

Article Biochemistry & Molecular Biology

Halogen bonding:: the σ-hole

Timothy Clark et al.

JOURNAL OF MOLECULAR MODELING (2007)

Article Chemistry, Physical

Accurate Coulomb-fitting basis sets for H to Rn

F Weigend

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2006)

Article Statistics & Probability

The distribution of robust distances

J Hardin et al.

JOURNAL OF COMPUTATIONAL AND GRAPHICAL STATISTICS (2005)