Yet another perspective on hole interactions

Tarannam, Naziha; Shukla, Rahul; Kozuch, Sebastian

doi:10.1039/d1cp03533a

Cited by 40 publications

(59 citation statements)

References 160 publications

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“…29,57,58 For more in-depth discussions on the nature of σ–hole interactions the interested reader is referred to recent reviews. 14,51,59–61…”

Section: Sigma–hole Interactions and Sensingmentioning

confidence: 99%

“…14 This notably includes (partial) charge transfer from the Lewis base into the s* orbital of the donor. 51 This interaction between an occupied orbital of the Lewis base guest and an empty donor orbital is not only highly directional, but can also be a substantial driving force for sigma-hole bonding, giving rise to a signicant degree of covalent character. 29,[52][53][54] This has also been experimentally observed for ChB interactions 29 as well as halide-XB complexes.…”

Section: Brief Introduction To Sigma-hole Interactionsmentioning

confidence: 99%

“…29,57,58 For more in-depth discussions on the nature of s-hole interactions the interested reader is referred to recent reviews. 14,51,[59][60][61] Of further note is that, depending on their hybridisation, ChB donors can form one (sp 2 ) or two sigma holes (sp 3 ). The "additional" substituent of sp 3 hybridised ChB donors (in comparison to only one substituent on typical XB or HB donors), hereby presents a potent means of further tuning the s-hole strength, or providing additional functionalities, such as optical or electrochemical reporter groups.…”

Section: Brief Introduction To Sigma-hole Interactionsmentioning

confidence: 99%

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Halogen bonding and chalcogen bonding mediated sensing

Hein

Beer

2022

Chem. Sci.

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“…29,57,58 For more in-depth discussions on the nature of σ–hole interactions the interested reader is referred to recent reviews. 14,51,59–61…”

Section: Sigma–hole Interactions and Sensingmentioning

confidence: 99%

Section: Brief Introduction To Sigma-hole Interactionsmentioning

confidence: 99%

Section: Brief Introduction To Sigma-hole Interactionsmentioning

confidence: 99%

See 1 more Smart Citation

Halogen bonding and chalcogen bonding mediated sensing

Hein

Beer

2022

Chem. Sci.

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“…Since the creation of the term "σ-hole" by Clark et al [1,2], the study of hole interactions has been the focus of recent attention in the field of noncovalent interactions [3]. The σ-hole bond was generally defined as a net attractive interaction between one electrophilic σ-hole and the other nucleophilic region [4,5].…”

Section: Introductionmentioning

confidence: 99%

The Bifurcated σ-Hole···σ-Hole Stacking Interactions

Wang

2022

Molecules

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The bifurcated σ-hole···σ-hole stacking interactions between organosulfur molecules, which are key components of organic optical and electronic materials, were investigated by using a combined method of the Cambridge Structural Database search and quantum chemical calculation. Due to the geometric constraints, the binding energy of one bifurcated σ-hole···σ-hole stacking interaction is in general smaller than the sum of the binding energies of two free monofurcated σ-hole···σ-hole stacking interactions. The bifurcated σ-hole···σ-hole stacking interactions are still of the dispersion-dominated noncovalent interactions. However, in contrast to the linear monofurcated σ-hole···σ-hole stacking interaction, the contribution of the electrostatic energy to the total attractive interaction energy increases significantly and the dispersion component of the total attractive interaction energy decreases significantly for the bifurcated σ-hole···σ-hole stacking interaction. Another important finding of this study is that the low-cost spin-component scaled zeroth-order symmetry-adapted perturbation theory performs perfectly in the study of the bifurcated σ-hole···σ-hole stacking interactions. This work will provide valuable information for the design and synthesis of novel organic optical and electronic materials.

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“…But chlorine and bromine tend to exhibit greater σ‐hole interactions with DNA base pairs, thus enhancing their ability to bind with biomolecules. [ 51 ] The lipophilic nature of the complexes ( C1–C4 ) due to the presence of PPh 3 also contributes to the enhanced cytotoxicity as seen in literature reports. [ 52 ]…”

Section: Resultsmentioning

confidence: 93%

Pd(II)–PPh₃ complexes of halogen substituted acylthiourea ligands: Biomolecular interactions and in vitro anti‐proliferative activity

Dorairaj

Haribabu

Chang

et al. 2022

Applied Organom Chemis

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Herein, we report the synthesis of four new Pd(II) acylthiourea complexes (C1–C4) to study the effect of halogen substituted acylthiourea ligands on the biological applications of their Pd(II)–PPh3 complexes. The complexes were characterized by various spectroscopic and analytical methods. The distorted square planar geometry of complexes was confirmed by single crystal X‐ray diffraction study, which also revealed the bidentate (N, S) coordination of the ligands with Pd(II). Interactions of the complexes with biomolecules (DNA/BSA) were investigated by spectroscopic and docking tools. All the complexes showed good binding ability with the targeted biomolecules. Further, in vitro anti‐proliferative activity of the complexes was investigated by performing MTT assay on cancer (HeLa‐cervical, HCT116‐colorectal, and HepG2‐hepatic) and normal (HEK293‐embryonic kidney) cell lines. All the complexes displayed remarkable activity on the three cancer cells, and among them, complex C2 bearing chlorine substituted acylthiourea showed superior activity on HeLa cells with an IC50 value of 6.5 μM, which was higher than that of cisplatin. Apoptosis induced by C2 on HeLa cells was assessed by AO/EB, DAPI and DNA laddering assays, and flow cytometry. Finally, the apoptotic efficiency of C2 was tested by cell cycle analysis, wherein the complex induced the cell cycle arrest in HeLa cells at G0/G1 phase.

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Yet another perspective on hole interactions

Abstract: Hole interactions are known by different names depending on the key atom of the bond (halogen bond, chalcogen bond, hydrogen bond, etc.), and the geometry of the interaction (σ if...

Cited by 40 publications

References 160 publications

Halogen bonding and chalcogen bonding mediated sensing

Halogen bonding and chalcogen bonding mediated sensing

The Bifurcated σ-Hole···σ-Hole Stacking Interactions

Pd(II)–PPh₃ complexes of halogen substituted acylthiourea ligands: Biomolecular interactions and in vitro anti‐proliferative activity

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Yet another perspective on hole interactions

Abstract: Hole interactions are known by different names depending on the key atom of the bond (halogen bond, chalcogen bond, hydrogen bond, etc.), and the geometry of the interaction (σ if...

Cited by 40 publications

References 160 publications

Halogen bonding and chalcogen bonding mediated sensing

Halogen bonding and chalcogen bonding mediated sensing

The Bifurcated σ-Hole···σ-Hole Stacking Interactions

Pd(II)–PPh3 complexes of halogen substituted acylthiourea ligands: Biomolecular interactions and in vitro anti‐proliferative activity

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Product

Resources

About

Pd(II)–PPh₃ complexes of halogen substituted acylthiourea ligands: Biomolecular interactions and in vitro anti‐proliferative activity