Chalcogen Bond as a Factor Stabilizing Ligand Conformation in the Binding Pocket of Carbonic Anhydrase IX Receptor Mimic DOI Open Access
Kamil Wojtkowiak, Mariusz Michalczyk, Wiktor Zierkiewicz

et al.

International Journal of Molecular Sciences, Journal Year: 2022, Volume and Issue: 23(22), P. 13701 - 13701

Published: Nov. 8, 2022

It is postulated that the overexpression of Carbonic Anhydrase isozyme IX in some cancers contributes to acidification extracellular matrix. was proved this promotes growth and metastasis tumor. These observations have made an attractive drug target. In light findings importance glycoprotein cancer treatment, we employed quantum-chemical approaches study non-covalent interactions binding pocket. As a ligand, acetazolamide (AZM) molecule chosen, being known as potential inhibitor exhibiting anticancer properties. First-Principles Molecular Dynamics performed chalcogen other AZM ligand its complexes with amino acids forming site. Based on Density Functional Theory (DFT) post-Hartree-Fock methods, metric electronic structure parameters were described. The Non-Covalent Interaction (NCI) index Atoms Molecules (AIM) methods applied for qualitative/quantitative analyses interactions. Finally, AZM-binding pocket interaction energy decomposition carried out. Chalcogen bonding important factor stabilizing preferred conformation. Free mapping via metadynamics Path Integral molecular dynamics confirmed significance bond structuring conformational flexibility systems. developed models are useful design new inhibitors desired pharmacological

Language: Английский

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers DOI
Paola Peluso, Bezhan Chankvetadze

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(16), P. 13235 - 13400

Published: Aug. 2, 2022

It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as fundamental phenomenon regulating life human activities. Thus, represent the narrative thread of fascinating story which goes across several disciplines medical, chemical, physical, biological, other natural sciences. This review has been conceived with awareness modern attitude toward its consequences needs to be founded on multidisciplinary approaches disclose basis essential phenomena domain With primary aim discussing this topic an integrated way, comprehensive pool rational systematic information provided, concerns fundamentals chirality, description interactions, their implications processes occurring different contexts. A specific focus devoted enantioselection chromatography electromigration techniques because unique feature "multistep" processes. second motivation for writing make clear statement about state art, tools we have at our disposal, what still missing fully understand mechanisms underlying recognition.

Language: Английский

Citations

174

Anion⋯anion self-assembly under the control of σ- and π-hole bonds DOI Creative Commons
Andrea Pizzi, Arun Dhaka, Roberta Beccaria

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(13), P. 6654 - 6674

Published: Jan. 1, 2024

The electrostatic attraction between charges of opposite signs and the repulsion same sign are ubiquitous influential phenomena in recognition self-assembly processes. However, it has been recently revealed that specific attractive forces ions with relatively common. These can be strong enough to overcome Coulomb sign, leading formation stable anion⋯anion cation⋯cation adducts. Hydroden bonds (HBs) probably best-known interaction effectively direct these counterintuitive assembly In this review we discuss how σ-hole π-hole break paradigm like-charges drive anions into discrete as well one-, two-, or three-dimensional σ-Hole regions excess electron density molecular entities (

Language: Английский

Citations

14

Aerogen Bond, Halogen Bond, Chalcogen Bond, Pnictogen Bond, Tetrel Bond, Triel Bond ... Why So Many Names? DOI
Robin Taylor

Crystal Growth & Design, Journal Year: 2024, Volume and Issue: 24(10), P. 4003 - 4012

Published: May 6, 2024

The nomenclature exemplified in this paper's title has more terms than necessary. It conceals the often-similar physical natures of noncovalent interactions that it names, and pointlessly imitates term used for most important interaction, hydrogen bond. In doing so, becomes inconsistent with naming style covalent several interactions. other shortcomings attracted criticism from quarters. is suggested here simplest alternative consists three terms: σ-hole π-hole p-hole interaction. first two are well-known often regarded as implying an electrostatic Given Hellmann–Feynman theorem, expectation completely satisfied. Additional could be σ- or almost but not quite hypervalent dative ("perihypervalent bond" "pericovalent suggested). With some exceptions, argued "interaction" should preferred to "bond". Effecting a change would difficult. best started by open objective exchange views on current state

Language: Английский

Citations

13

Definition of the Halogen Bond (IUPAC Recommendations 2013): A Revisit DOI
Pradeep R. Varadwaj, Arpita Varadwaj, Helder M. Marques

et al.

Crystal Growth & Design, Journal Year: 2024, Volume and Issue: 24(13), P. 5494 - 5525

Published: June 24, 2024

This Article revisits the "Definition of Halogen Bond (IUPAC Recommendations 2013)" [Desiraju, G. R. Pure Appl. Chem. 2013, 85 (8), 1711–1713], recommendations that fail to include fundamental, underlying concept (electrophilic) σ- and p-/π-hole theory orbital-based charge transfer interactions accompany halogen bond formation. An electrophilic σ-hole, or p-/π-hole, is an electron-density-deficient region positive polarity (and potential) on electrostatic surface side along, orthogonal to, a covalently bonded in molecular entity leads development noncovalent interaction─a bond─when close proximity electron-density-rich nucleophilic same another identical different entity, with which it interacts. re-examines characteristic features lists wide variety donors acceptors participate bonding. We add caveats are essential for identifying bonding chemical systems, necessary appropriate use terminologies involved. Illustrative examples systems feature inter- intramolecular bonds other crystalline phase given, together case study some dimer using first-principles calculations. also point out π-hole/belt (or p-hole/belt) may develop derivative halogenated molecules be prone forming when nucleophiles similar entity.

Language: Английский

Citations

10

Yet another perspective on hole interactions DOI
Naziha Tarannam, Rahul Shukla, Sebastian Kozuch

et al.

Physical Chemistry Chemical Physics, Journal Year: 2021, Volume and Issue: 23(36), P. 19948 - 19963

Published: Jan. 1, 2021

Hole interactions are known by different names depending on their key atom ( e.g. halogen, chalcogen, triel or hydrogen bonds), and the geometry of interaction (σ, π, δ). Maybe we can make some order analysing molecular orbitals?

Language: Английский

Citations

44

Te⋯N secondary-bonding interactions in tellurium crystals: Supramolecular aggregation patterns and a comparison with their lighter congeners DOI
Edward R. T. Tiekink

Coordination Chemistry Reviews, Journal Year: 2022, Volume and Issue: 457, P. 214397 - 214397

Published: Jan. 21, 2022

Language: Английский

Citations

30

A new look at the chalcogen bond: π-hole-based chalcogen (Se, Te) bonding which does not include a σ-hole interaction DOI
Eugene A. Katlenok, Maxim L. Kuznetsov, Nikolay A. Semenov

et al.

Inorganic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(10), P. 3065 - 3081

Published: Jan. 1, 2023

Chalcogen bonding which does not include σ-hole interaction.

Language: Английский

Citations

17

Importance of π-π interactions in the solid state structures of two cobalt complexes derived from N,O donor reduced Schiff base ligands DOI
Rabi Sankar Sarkar, Snehasis Banerjee, Shouvik Chattopadhyay

et al.

Polyhedron, Journal Year: 2024, Volume and Issue: 254, P. 116916 - 116916

Published: Feb. 29, 2024

Language: Английский

Citations

6

Principles Guiding the Square Bonding Motif Containing a Pair of Chalcogen Bonds between Chalcogenadiazoles DOI
Steve Scheiner

The Journal of Physical Chemistry A, Journal Year: 2022, Volume and Issue: 126(7), P. 1194 - 1203

Published: Feb. 10, 2022

The bonding motif adopted by a dimer of chalcogenadiazole molecules is characterized pair equivalent Ch···N chalcogen bonds. Quantum calculations show that the interaction energy substantial, varying between 4 kcal/mol for Ch = S and 17 Te. cooperative in total bond strength greater than either individually. Neither addition phenyl ring nor cyano substituents to diazole has much influence on this binding. Removal one N from weakens binding, two nitrogens little effect. largest perturbation arises with three atoms each ring, which binding increases some 25%. size plays minor role most cases, although near doubling occurs if there are present four-membered ring.

Language: Английский

Citations

20

Halogen Bond via an Electrophilic π-Hole on Halogen in Molecules: Does It Exist? DOI Open Access
Pradeep R. Varadwaj

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(9), P. 4587 - 4587

Published: April 23, 2024

This study reveals a new non-covalent interaction called π-hole halogen bond, which is directional and potentially non-linear compared to its sister analog (σ-hole bond). A shown here be observed on the surface of in halogenated molecules, can tempered display aptness form bond with series electron density-rich sites (Lewis bases) hosted individually by 32 other partner molecules. The [MP2/aug-cc-pVTZ] level characteristics bonds 33 binary complexes obtained from charge density approaches (quantum theory intramolecular atoms, molecular electrostatic potential, independent gradient model (IGM-δginter)), intermolecular geometries energies, second-order hyperconjugative transfer analyses are discussed, similar interactions. That molecules substantiated experimentally reported crystals documented Cambridge Crystal Structure Database. importance design growth chemical systems synthetic chemistry, crystallography, crystal engineering yet fully explicated.

Language: Английский

Citations

5