On the nature of non-covalent interactions in isomers of 2,5-dichloro-1,4-benzoquinone dimers – ground- and excited-state properties

Pandiyan, B. Vijaya; Deepa, P.; Kolandaivel, P.

doi:10.1039/c4cp02484b

Cited by 16 publications

(2 citation statements)

References 48 publications

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“…Work over the years has shown that this bonding mechanism is not limited to the halogen family but extends as well to other atoms, some less electronegative than others . Depending upon the column of the periodic table to which the bridging atom belongs, these noncovalent bonds have been denoted as chalcogen (6A), − pnicogen (5A), ,− and tetrel (4A) − bonds.…”

Section: Introductionmentioning

confidence: 99%

Comparison of CH···O, SH···O, Chalcogen, and Tetrel Bonds Formed by Neutral and Cationic Sulfur-Containing Compounds

Scheiner

2015

J. Phys. Chem. A

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The ability of neutral and charged S-compounds to form different sorts of noncovalent bonds is examined by ab initio calculations. Neutrals are represented by CH3SH and fluoro-substituted FSCH3; cations are (CH3)3S(+), CH3SH2(+), and FHSCH3(+). Each is paired with N-methylacetamide (NMA) whose O atom serves as a common electron donor. Charged species engage in much stronger noncovalent bonds than do the neutral molecules, by as much as an order of magnitude. The strongest noncovalent bond for any system is a O···SF chalcogen bond wherein the O lies directly opposite a S-F covalent bond, amounting to as much as 39 kcal/mol. Second in binding energy is the SH···O H-bond, which can be as large as 34 kcal/mol. Somewhat weaker is the O···SC chalcogen bond, followed by the CH···O H-bond and finally the O···C tetrel bond, which has the appearance of a trifurcated H-bond. Any CH group that participates in a CH···O H-bond shifts its NMR signal downfield by an amount roughly proportional to the strength of the H-bond. This situation is clearly distinguishable from that in a O···S chalcogen or SH···O H-bond wherein the methyl protons are shifted upfield.

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Section: Introductionmentioning

confidence: 99%

Comparison of CH···O, SH···O, Chalcogen, and Tetrel Bonds Formed by Neutral and Cationic Sulfur-Containing Compounds

Scheiner

2015

J. Phys. Chem. A

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“…This Coulombic attraction is supplemented by the transfer of charge from the neighboring molecule's lone electronp airs into the CÀX s*a ntibonding orbital under the rubric of polarization or induction energy.A dditional attraction arises by way of Londond ispersion forces. It is worthwhile to notet hat this bondingm echanism is not limited to halogen atoms, but has been observed for chalcogen, [13][14][15][16][17][18][19][20][21] pnicogen, [12,[22][23][24][25][26][27][28] and tetrel [29][30][31][32][33][34][35][36] atoms in the eponymous bonds.…”

Section: Introductionmentioning

confidence: 99%

Competitive Halide Binding by Halogen Versus Hydrogen Bonding: Bis‐triazole Pyridinium

Nepal

Scheiner

2015

Chemistry A European J

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The binding of F(-) , Cl(-) , Br(-) , and I(-) anions by bis-triazole-pyridine (BTP) was examined by quantum chemical calculations. There is one H atom on each of the two triazole rings that chelate the halide via H bonds. These H atoms were replaced by halogens Cl, Br, and I, thus substituting H bonds by halogen bonds. I substitution strongly enhances the binding; Br has a smaller effect, and Cl weakens the interaction. The strength of the interaction is sensitive to the overall charge on the BTP, rising as the binding agent becomes singly and then doubly positively charged. The strongest preference of a halide for halogenated as compared to unsubstituted BTP, as much as several orders of magnitude, is observed for I(-) . Both unsubstituted and I-substituted BTP could be used to selectively extract F(-) from a mixture of halides.

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Does the presence of water clusters induce the binding affinity of CK2 halogen ligands?: A quantum chemical perspective study

Deepa

Pandiyan

Kolandaivel

2018

Int J of Quantum Chemistry

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Protein-ligand interaction is the key factor in modeling of drugs and water molecules act as a bridge in linking protein and ligand, which was clearly depicted by Deepa (Cryst. Growth Des. 2017, 17, 1299. This work is intended toward the significance of water cluster in the midst of ligand binding. Further the idea was accounted to have in-depth analysis of the individual water molecules that interact with each part of the ligand, since in reality only very few crystal water molecules bind with the CK2 ligands. Further, bulk solvent effects have been modeled using Tomasi's polarized continuum model at M06-2X/def2-QZVP levels of theory has increased the stability of the complexes. The strength of individual water molecules and their binding nature with ligand will be depicted in detail by interaction energy and two body interaction energy calculations at M06-2X/def2-QZVP level of theory. The impact of noncovalent interactions (Hydrogen, r-hole and P-hole bonding) in bridging between water cluster cavity and ligand were deeply analysed using structural properties (bond distance and bond angle), 2DNCI plot, AIM and NBO analyses.The HOMO, LUMO energy values are discussed in detail for both monomer (ligand) and complexes (ligand with water clusters). It is expected that this study paves a novel path for the scientific community in modeling drugs with the clear understanding of the impact of water molecules on ligand. K E Y W O R D SAIM, r and P-hole, HOMO, interaction energy, LUMO, NBO analyses 1 | I N TR ODU C TI ON Water is a "mother liquid" essential for the existence of living beings. Life and water goes hand in hand, where the survival of living beings is solely depend on water molecules. Living cells are engaged by excess volume of water molecules (i.e., more than 60%) and the decrease in volume of water, that is, 10-20% source the cell death. Biomolecules compiling cells are regularly immersed within an aqueous atmosphere and encompass exclusive structures for their biological activities. [1] When "heavy water" replaces the "light water" of living cells, the homeostasis of cells is drastically changed. While the chemical properties of the above waters look similar but, their physical properties differ. Hence, to focus water as the key factor in biological interaction, many studies have deliberated the interactions between water and biomolecules, [2] specifically in proteins. [3] This study is attempted to have some basic knowledge about the influence of water environment on the halogenated CK2 ligands.Water molecules are able to alter the flexibility of the ligand in a protein molecule, thus enhancing the protein-ligand binding nature. Proteinligand interaction is the key factor in modeling of drugs and it was clearly depicted by Deepa [4] that water molecules act as a bridge in linking protein and ligand. In general crystal waters are implicated in protein-ligand interaction either by inter mediating the hydrogen bonds between the protein and the ligand thus enhancing the binding nature or by being exiled by...

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On the nature of non-covalent interactions in isomers of 2,5-dichloro-1,4-benzoquinone dimers – ground- and excited-state properties

Cited by 16 publications

References 48 publications

Comparison of CH···O, SH···O, Chalcogen, and Tetrel Bonds Formed by Neutral and Cationic Sulfur-Containing Compounds

Comparison of CH···O, SH···O, Chalcogen, and Tetrel Bonds Formed by Neutral and Cationic Sulfur-Containing Compounds

Competitive Halide Binding by Halogen Versus Hydrogen Bonding: Bis‐triazole Pyridinium

Does the presence of water clusters induce the binding affinity of CK2 halogen ligands?: A quantum chemical perspective study

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