In Silico Characterization and Prediction of Thiourea-like Neutral Bidentate Halogen Bond Catalysts

2021 ◽  
Author(s):  
Hui Yang ◽  
Choon-Hong Tan ◽  
Ming Wah Wong
Keyword(s):  
In Silico ◽  
Halogen Bond ◽  
Steric Interaction ◽  
Halogen Bonds ◽  
Common Strategy ◽  
Non Covalent Interactions ◽  
Neutral Bidentate ◽  
In Silico Characterization ◽  
Covalent Interactions

Preorganization is a common strategy to align halogen bond (XB) donors to form two or more halogen bonds simultaneously. Previous approaches have utilized various non-covalent interactions such as steric interaction,...

Tetrachloromethane as halogen bond donor toward metal-bound halides

2019 ◽  
Vol 234 (1) ◽  
pp. 9-17 ◽  
Author(s):  
Lev E. Zelenkov ◽  
Daniil M. Ivanov ◽  
Margarita S. Avdontceva ◽  
Alexander S. Novikov ◽  
Nadezhda A. Bokach
Keyword(s):  
Dft Calculations ◽  
Electron Density Distribution ◽  
Halogen Bond ◽  
Topological Analysis ◽  
Halogen Bonds ◽  
Chloride Complexes ◽  
X Ray ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Supramolecular Contacts

Abstract Two annulated triazapentadiene systems, viz. 1,3,5,7,9-pentaazanona-1,3,6,8-tetraenate chloride complexes of PtII, form CCl4 solvates, containing the Cl3C–Cl···Cl–Pt halogen bonds. These halogen bonds are firstly reported type of Cl3C–Cl···Cl–M contacts. In the X-ray structures of two solvates different non-covalent interactions were detected and studied by DFT calculations and topological analysis of the electron density distribution within the framework of QTAIM method at the M06/DZP-DKH level of theory. Estimated energies of these supramolecular contacts vary from 0.6 to 2.4 kcal/mol.

scholarly journals Strength of the [Z–I···Hal]− and [Z–Hal···I]− Halogen Bonds: Electron Density Properties and Halogen Bond Length as Estimators of Interaction Energy

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 2083
Author(s):  
Maxim L. Kuznetsov
Keyword(s):  
Bond Length ◽  
Interaction Energy ◽  
Electron Density ◽  
Halogen Bond ◽  
Bond Critical Point ◽  
Halogen Bonds ◽  
Curvature Potential ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Bond energy is the main characteristic of chemical bonds in general and of non-covalent interactions in particular. Simple methods of express estimates of the interaction energy, Eint, using relationships between Eint and a property which is easily accessible from experiment is of great importance for the characterization of non-covalent interactions. In this work, practically important relationships between Eint and electron density, its Laplacian, curvature, potential, kinetic, and total energy densities at the bond critical point as well as bond length were derived for the structures of the [Z–I···Hal]– and [Z–Hal···I]– types bearing halogen bonds and involving iodine as interacting atom(s) (totally 412 structures). The mean absolute deviations for the correlations found were 2.06–4.76 kcal/mol.

scholarly journals New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

2016 ◽  
Vol 12 ◽  
pp. 2834-2848 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Recent Progress ◽  
Halogen Bonds ◽  
Hydrogen Bond Donor ◽  
New Approaches ◽  
Substrate Activation ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Hydrogen Bond Donors

Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

Solid-State NMR at the University of Ottawa

2015 ◽  
Vol 93 (5) ◽  
pp. 485-491
Author(s):  
David L. Bryce
Keyword(s):  
Solid State ◽  
Solid State Nmr ◽  
Materials Characterization ◽  
Canadian Society ◽  
Halogen Bonds ◽  
Biomolecular Nmr ◽  
Non Covalent Interactions ◽  
Nmr Crystallography ◽  
The University ◽  
Covalent Interactions

This article describes some highlights of the research which has been carried out in my laboratory at the University of Ottawa over the period covering 2005 to 2014. My research is in the general areas of solid-state NMR, applications of quantum chemistry, and biomolecular NMR. The format will follow that of my 2014 Canadian Society for Chemistry Keith Laidler Award presentation given in Vancouver in June 2014 at the 97th Canadian Chemistry Conference and Exhibition. Following a brief introduction, I will present some of our most interesting and exciting recent advances according to the following six themes: 1. Fundamental solid-state NMR. 2. Materials characterization and NMR crystallography. 3. Pharmaceuticals and polymorphism. 4. Non-covalent interactions: Halogen bonds. 5. Biomolecular NMR. 6. Software development.

Color-tunable phosphorescence of 1,10-phenanthrolines by 4,7-methyl/-diphenyl/-dichloro substituents in cocrystals assembledviabifurcated C—I...N halogen bonds using 1,4-diiodotetrafluorobenzene as a bonding donor

2017 ◽  
Vol 73 (2) ◽  
pp. 247-254 ◽  
Author(s):  
Rui Liu ◽  
Yuan Jun Gao ◽  
Wei Jun Jin
Keyword(s):  
Noncovalent Interactions ◽  
Halogen Bonding ◽  
Luminescent Properties ◽  
Halogen Bonds ◽  
X Ray Diffraction ◽  
X Ray ◽  
Color Tunable ◽  
Non Covalent Interactions ◽  
The Impact ◽  
Covalent Interactions

Single-crystal X-ray diffraction reveals a series of phosphorescent cocrystals which were assembled by 1,4-diiodotetrafluorobenzene (1,4-DITFB) and either 4,7-dimethyl-1,10-phenanthroline (DMPhe), 4,7-diphenyl-1,10-phenanthroline (DPPhe) or 4,7-dichloro-1,10-phenanthroline (DClPhe)viaC—I...N halogen bonding. These cocrystals, labeled (1), (2) and (3), respectively, are phosphorescent and a distinct change in phosphorescent color can be observed from orange–yellow, green to yellow–green, with well defined vibrational band maxima at 587, 520 and 611 nm for (1), (2) and (3). Based on the dependence of halogen bonding in sites and strength, we discussed the impact of substituents with different electron-withdrawing effects and steric hindrance on intermolecular noncovalent interactions and phosphorescence. The method of inducing and modulating phosphorescence by halogen bonding and other weak non-covalent interactions through changing the substituent groups of molecules should be significant in both theory and the application of optical function materials with predictable and modulated luminescent properties.

scholarly journals Interplay of Halogen and Hydrogen Bonding in a Series of Heteroleptic iron(III) Complexes

2021 ◽  
Author(s):  
Raúl Díaz-Torres ◽  
Jorge Echeverría ◽  
Oliver Loveday ◽  
Phimphaka Harding ◽  
David Harding
Keyword(s):  
Molecular Electrostatic Potential ◽  
Crystal Packing ◽  
Halogen Bonds ◽  
Heteroleptic Complexes ◽  
1D Chain ◽  
Nci Analysis ◽  
Non Covalent Interactions ◽  
Uv Visible ◽  
Hammett Parameter ◽  
Covalent Interactions

<div>The influence of the halogen substituent on crystal packing and redox properties is investigated in a series of heteroleptic complexes [Fe(qsal-X)(dipic)]MeOH (qsal-X = 4-halogen-2-[(8-quinolylimino)methyl]phenolate; dipic = 2,6-pyridinedicarboxylate; X = F 1, Cl 2, Br 3 and I 4).</div><div>Compounds 1 and 2 exhibit triclinic symmetry (P1̅), whereas 3 and 4 crystallise in monoclinic P21/n. The crystal packing shows self-sorting of the ligands with - interactions between the qsal-X ligands and overlap of the dipic ligands to form a 1D chain, that is supported by C-H···O interactions. In 1 and 2, the cross-section of the 1D chain is square, while for 3 and 4, it is rectangular. In the former, the dipic ligands interact through C=O··· interactions, while - interactions are found in 3 and 4. Neighbouring chains are connected via - interactions involving the quinoline rings, but their relative position is driven by the preference of 1 and 2, for C-H···X interactions, whereas 3 and 4 form O···X halogen bonds. The nature and topology of the electron density of these interactions have been investigated using molecular electrostatic potential (MEP) mapping, quantum theory of atoms in molecules (QTAIM) and ‘non-covalent interactions’ (NCI) analysis. UV-Visible experiments show MLCT bands associated with the qsal-X ligands, confirming the structure is stable in solution. Electrochemical studies reveal slight tuning of the Fe3+/Fe2+ redox couple showing a linear relationship between E° and the Hammett parameter σp.</div><div><br></div>

scholarly journals The Hydrogen Bond, the Halogen Bond and Rotational Spectroscopy: A Personal Retrospective

2019 ◽  
Vol 100 (1) ◽  
pp. 191-202
Author(s):  
Anthony Legon
Keyword(s):  
Hydrogen Bond ◽  
Experimental Work ◽  
Research Group ◽  
Halogen Bond ◽  
Rotational Spectroscopy ◽  
Non Covalent Interactions ◽  
Covalent Interactions

AbstractThis article is a personal, chronological account of experimental work carried out on the hydrogen bond, the halogen bond and other non-covalent interactions by my research group using (mainly) rotational spectroscopy since 1974. It is not intended to be comprehensive, and therefore does not include contributions made by many groups in the last 40 years or so.

Components of the interaction energy of the odd-electron halogen bond: an ab initio study

2020 ◽  
Vol 22 (27) ◽  
pp. 15389-15400
Author(s):  
Prasanta Bandyopadhyay ◽  
Md. Motin Seikh
Keyword(s):  
Ab Initio ◽  
Interaction Energy ◽  
Halogen Bond ◽  
Conceptual Dft ◽  
Ab Initio Study ◽  
Fertile Ground ◽  
Non Covalent Interactions ◽  
Covalent Interactions

The odd-electron halogen bond offers a fertile ground to explore the nature of non-covalent interactions. The regioselectivity, interaction energy and its components were analyzed by conceptual DFT parameters, NCI plot and LED-DLPNO-CCSD(T) analysis.

scholarly journals In silico decryption of serotonin–receptor binding: local non-covalent interactions and long-range conformational changes

RSC Advances ◽  
2020 ◽  
Vol 10 (62) ◽  
pp. 37995-38003
Author(s):  
Padmabati Mondal
Keyword(s):  
Long Range ◽  
Receptor Binding ◽  
Conformational Changes ◽  
In Silico ◽  
Serotonin Receptor ◽  
Receptor Complexes ◽  
Serotonin Receptor Binding ◽  
Non Covalent Interactions ◽  
The Stability ◽  
Covalent Interactions

This study is focused on identifying the main non-covalent interactions controlling the stability of serotonin–receptor complexes as well as the main conformational changes in the receptor due to serotonin–receptor binding.

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