Thiourea-Based Tritopic Halogen-Bonding Acceptors

Article Chemistry, Multidisciplinary

Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds

Asia Marie S. Riel et al.

Summary: The halogen bond donor is strengthened by direct interaction with a hydrogen bond, which plays a key role in a catalyst enhancing product conversion in a halide abstraction reaction over traditional halogen bonding derivatives.

CHEMICAL COMMUNICATIONS (2022)

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Article Crystallography

Synthesis of Thiosemicarbazones and Their Organoiodine Cocrystals: Cooperative Effects of Halogen and Hydrogen Bonding

Andrew J. Peloquin et al.

Summary: Nine thiosemicarbazones were synthesized by utilizing the facile addition-elimination reaction of thiosemicarbazide with acetone or aldehydes. The synthesis was conducted in situ with common halogen bond donors, resulting in the characterization of 12 new cocrystals showcasing halogen bonding and sulfur-chalcogen bonding. The intermolecular interactions involving organic iodines linking chains led to the formation of double-stranded chains, ribbons, and sheets.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY (2022)

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Article Chemistry, Multidisciplinary

Halogen, chalcogen, and hydrogen bonding in organoiodine cocrystals of heterocyclic thiones: imidazoliame-2-thione, 2-mercaptobenzimidazole, 2-mercapto-5-methylbenzimidazole, 2-mercaptobenzoxazole, and 2-mercaptobenzothiazole

Spencer Watts et al.

Summary: By combining heterocyclic thiones with variation in the identity of the heterocyclic elements, a series of 18 new crystalline structures were characterized. N-H...S hydrogen bonding was observed in most cases, resulting in two-dimensional motifs or dimeric pairs. The packing was consolidated through C-I...S and C-I...I halogen bonding, as well as C=S...I chalcogen bonding, linking the hydrogen-bonding ribbons or dimeric pairs.

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Heterocyclic 1,3-diazepine-based thiones and selones as versatile halogen-bond acceptors

Arianna C. Ragusa et al.

Summary: Utilizing N-heterocyclic chalcogenones as halogen-bond acceptors, a total of 24 new cocrystals were prepared. By reacting with molecular diiodine and undergoing oxidative addition of acetone, different types of halogen and covalent bonds were formed. Common halogen-bond donors also facilitated cocrystal formation. The cocrystals of SDiazMesS and SDiazMesSe showed similar crystal structures.

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS (2022)

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Article Chemistry, Multidisciplinary

Halogen Bonds of Iodonium Ions: A World Dissimilar to Silver Coordination

Lotta Turunen et al.

Summary: The distinct difference between the three-center halogen bond and the analogous three-center coordinative bond of silver is demonstrated through computational, X-ray crystallographic, and solution NMR spectroscopic investigations of their complexes with a bidentate Lewis base. Iodine(I) tends to form entropically favored monomeric complexes, while silver(I) forms enthalpically favored dimeric complexes. The structure of the silver complexes is significantly influenced by counterion coordination in both solution and solid state, in contrast to the minimal effect it has on the analogous halogen bond.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2021)

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Article Chemistry, Inorganic & Nuclear

The Se ••• Hal halogen bonding: Co-crystals of selenoureas with fluorinated organohalides

Maria Chernysheva et al.

Summary: The synthesis and structural characterization of binary co-crystals 1-4 involving selenourea and halogen donors were reported. It was found that selenium forms stronger halogen bonds with halogens compared to sulfur. The interaction energies, Hirschfeld, and QTAIM analyses supported the observation that selenium-based XB acceptors result in slightly stronger halogen bonding.

JOURNAL OF SOLID STATE CHEMISTRY (2021)

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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)

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Article Chemistry, Multidisciplinary

Anion Binding Studies of Urea and Thiourea Functionalized Molecular Clefts

Utsab Manna et al.

Summary: Two rationally designed molecular clefts based on 4-nitrophenyl, functionalized with thiourea (L (1)) and urea (L (2)), have been synthesized and studied for various anions in DMSO using UV-Vis and colorimetric techniques. Both L (1) and L (2) were found to form 1:1 complexes with halides and oxoanions, with L (1) exhibiting stronger affinity for anions compared to L (2) due to the presence of more acidic thiourea functional groups.

FRONTIERS IN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Halogen Bonding between Thiocarbonyl Compounds and 1,2-and 1,4-Diiodotetrafluorobenzenes

Lauri Happonen et al.

Summary: This study investigated the halogen bonding between DITFBs and thiocarbonyl acceptors using single-crystal X-ray diffraction. The results showed that the lengths of contacts in the complexes were shorter than the sum of van der Waals radii and the contact angles were close to linear, confirming the existence of halogen bonding interactions. The solid-state packing of thiocarbonyl-XB complexes was greatly influenced by the size and type of the acceptor, with sulfur atoms capable of accepting multiple XB interactions.

CRYSTAL GROWTH & DESIGN (2021)

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Article Chemistry, Multidisciplinary

Halogen and Chalcogen Bonding Between the Triphenylphosphine Chalcogenides (Ph3P=E; E=O, S, Se) and Iodofluorobenzenes

Andrew J. Peloquin et al.

Summary: This study investigates the roles of chalcogen and halogen bonding in the formation of cocrystals of Ph3P=E (E=O, S, Se) with organoiodines. Different structures and interactions were observed among the chalcogenides and organoiodines, with some selenium...organoiodine ChB formations being rare examples. The strength of the interactions was analyzed using natural bond orbital (NBO) theory, with calculated energies falling between 3.14 kcal/mol and 12.81 kcal/mol.

CHEMPLUSCHEM (2021)

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Article Chemistry, Multidisciplinary

Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents

Andrew J. Peloquin et al.

Summary: This article discusses a new deep eutectic solvent based on halogen bonding, which is different from the majority of DESs that rely on ionic components. The newly developed deep eutectic solvent remains in liquid form, with a eutectic melting temperature at different 1,3-dithiane mole fractions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Interplay of Halogen and Hydrogen Bonding through Co-Crystallization in Pharmacologically Active Dihydropyrimidines: Insights from Crystal Structure and Energy Framework

Keshab M. Bairagi et al.

Summary: A solvent-assisted grinding method was used to prepare co-crystals in substituted dihydropyrimidines, which are pharmacologically active compounds. The co-crystals were characterized using various methods and analyzed to explore the formation mechanisms of XB and HB synthons in the solid state. The study revealed that the stability of the co-crystals is enhanced through a combination of electrostatics and dispersion effects via XB/HB interactions.

CHEMPLUSCHEM (2021)

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Article Chemistry, Multidisciplinary

The reaction of thiourea and 1,3-dimethylthiourea towards organoiodines: oxidative bond formation and halogen bonding

Andrew J. Peloquin et al.

Summary: By varying the halogen-bond-donor molecules, 11 new halogen-bonding cocrystals were obtained, demonstrating bifurcated I-S-I interactions and the characterization of sulfonium-containing products in the solid state.

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Halogen bonding in polymer science: towards new smart materials

Robin Kampes et al.

Summary: The halogen bond, while underrepresented in polymer science, shows great potential for designing polymeric materials. Applications of halogen bonding in self-assembly, photo-responsive materials, and self-healing materials are currently expanding.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

Halogen Bonding in Two-Dimensional Crystal Engineering

Joan Teyssandier et al.

CHEMISTRYOPEN (2020)

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Article Crystallography

A Novel Halogen Bond Acceptor: 1-(4-Pyridyl)-4-Thiopyridine (PTP) Zwitterion

Xin Ding et al.

CRYSTALS (2020)

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Article Chemistry, Multidisciplinary

Halogen Bonding Helicates Encompassing Iodonium Cations

Alan Vanderkooy et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Review Chemistry, Physical

Halogen Bonding beyond Crystals in Materials Science

Marco Saccone et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2019)

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Article Chemistry, Multidisciplinary

Tuning the solubility of ionophores: glutathione-mediated transport of chloride ions across hydrophobic membranes

Nasim Akhtar et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Halogen-Bonded Supramolecular Capsules in the Solid State, in Solution, and in the Gas Phase

Oliver Dumele et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Applied

A Case Study of Thiourea-Assisted Iminium Formation by Hydroxyl Anion Binding: Kinetic, Spectroscopic and Computational Evidences

Veronica Juste-Navarro et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Tetrameric and Dimeric [N•••I+•••N] Halogen-Bonded Supramolecular Cages

Lotta Turunen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Article Chemistry, Multidisciplinary

[NI+N] Halogen-Bonded Dimeric Capsules from Tetrakis(3-pyridyl)ethylene Cavitands

Lotta Turunen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Review Chemistry, Multidisciplinary

The Halogen Bond

Gabriella Cavallo et al.

CHEMICAL REVIEWS (2016)

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Article Chemistry, Multidisciplinary

Halogen Bonding in Organic Synthesis and Organocatalysis

David Bulfield et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

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Article Chemistry, Physical

Anion Binding of One-, Two-, and Three-Armed Thiourea Receptors Examined via Photoelectron Spectroscopy and Quantum Computations

Evgeny V. Beletskiy et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2016)

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Article Chemistry, Multidisciplinary

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Filip Topic et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Multidisciplinary

A Halogen-Bonded Dimeric Resorcinarene Capsule

Ngong Kodiah Beyeh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Halogen Bonding Molecular Capsules

Oliver Dumele et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Sterically geared tris-thioureas; transmembrane chloride transporters with unusual activity and accessibility

Hennie Valkenier et al.

CHEMICAL COMMUNICATIONS (2015)

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Article Chemistry, Multidisciplinary

Investigating C=S•••I Halogen Bonding for Cocrystallization with Primary Thioamides

Kevin S. Eccles et al.

CRYSTAL GROWTH & DESIGN (2015)

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Article Chemistry, Multidisciplinary

Halogen bonds with coordinative nature: halogen bonding in a S-I+-S iodonium complex

L. Koskinen et al.

CRYSTENGCOMM (2015)

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Review Chemistry, Multidisciplinary

Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different

Arijit Mukherjee et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

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Review Chemistry, Multidisciplinary

The Cambridge Structural Database in Retrospect and Prospect

Colin R. Groom et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Chemistry, Physical

Practical crystal engineering using halogen bonding: A hierarchy based on calculated molecular electrostatic potential surfaces

Christer B. Aakeroey et al.

JOURNAL OF MOLECULAR STRUCTURE (2014)

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Article Chemistry, Medicinal

Principles and Applications of Halogen Bonding in Medicinal Chemistry and Chemical Biology

Rainer Wilcken et al.

JOURNAL OF MEDICINAL CHEMISTRY (2013)

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Article Chemistry, Physical

Halogen bonding and other sigma-hole interactions: a perspective

Peter Politzer et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2013)

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Article Chemistry, Multidisciplinary

First supramolecular sensors for phosphonate anions

Nina A. Esipenko et al.

CHEMICAL SCIENCE (2013)

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Article Chemistry, Organic

(How) does 1,3,5-triethylbenzene scaffolding work? Analyzing the abilities of 1,3,5-triethylbenzene- and 1,3,5-trimethylbenzene-based scaffolds to preorganize the binding elements of supramolecular hosts and to improve binding of targets

Xing Wang et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2012)

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Review Chemistry, Inorganic & Nuclear

Halogen bonding in metal-organic-supramolecular networks

Roberta Bertani et al.

COORDINATION CHEMISTRY REVIEWS (2010)

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Article Chemistry, Multidisciplinary

The thiocyanate anion as a polydentate halogen bond acceptor

Pascal Cauliez et al.

CRYSTENGCOMM (2010)

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Article Biochemistry & Molecular Biology

Expansion of the σ-hole concept

Jane S. Murray et al.

JOURNAL OF MOLECULAR MODELING (2009)

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Review Chemistry, Multidisciplinary

Halogen bonding in supramolecular chemistry

Pierangelo Metrangolo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Article Chemistry, Multidisciplinary

A facile and convenient method for synthesis of alkyl thiocyanates under homogeneous phase transfer catalyst conditions

Ali Reza Kiasat et al.

CHINESE CHEMICAL LETTERS (2008)

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Article Chemistry, Physical

Enhanced anion binding of N-(Anilino)thioureas.: Contribution of the N-anilino -NH proton acidity

Zhao Li et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2008)

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Article Chemistry, Organic

Self-assembly of nitroxide radicals via halogen bonding -: directional NO•...;I interactions

K Boubekeur et al.

TETRAHEDRON LETTERS (2006)

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Article Biochemistry & Molecular Biology

Ab initio computational insight into the ion-pair S(N)2 reaction of lithium isothiocyanate and methyl fluoride in the gas phase and in acetone solution

Y Ren et al.

JOURNAL OF MOLECULAR MODELING (2006)

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Article Chemistry, Multidisciplinary

Crystal engineering through halogen bonding. 2. Complexes of diacetylene-linked heterocycles with organic iodides

A Crihfield et al.

CRYSTAL GROWTH & DESIGN (2003)

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Article Chemistry, Multidisciplinary

Noncovalent interactions in 2-mercapto-1-methylimidazole complexes with organic iodides

JI Jay et al.

CRYSTAL GROWTH & DESIGN (2001)

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Article Chemistry, Multidisciplinary

Crystal engineering through halogen bonding: Complexes of nitrogen heterocycles with organic iodides

RB Walsh et al.

CRYSTAL GROWTH & DESIGN (2001)

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Thiourea-Based Tritopic Halogen-Bonding Acceptors

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