Non-Covalent Interactions in Organic, Organometallic, and Inorganic Supramolecular Systems Relevant for Medicine, Materials Science, and Catalysis

Novikov, Alexander S.

doi:10.3390/cryst12020246

Cited by 17 publications

(11 citation statements)

References 21 publications

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“…An alternative strategy, based on the complexation of harmful substances [ 9 , 10 , 11 , 12 ] by macrocyclic systems offers new perspectives to address the issue of capturing and storing hazardous substances. Supramolecular chemistry is mainly concerned with the study of the host-guest complexes in which two or more neutral or charged molecules bind to each other via non-covalent interactions [ 13 , 14 , 15 ]; these interactions are the main driving forces of the complexation process, which leads to the modification of the physicochemical properties of host-guest complexes [ 16 , 17 , 18 , 19 , 20 ]. Among the supramolecular systems, cyclodextrins [ 21 , 22 ], cucurbiturils [ 23 , 24 , 25 ], calixarenes [ 26 , 27 , 28 , 29 ], and pillararenes [ 30 , 31 , 32 ] are the most studied host compounds.…”

Section: Introductionmentioning

confidence: 99%

In Search of Preferential Macrocyclic Hosts for Sulfur Mustard Sensing and Recognition: A Computational Investigation through the New Composite Method r2SCAN-3c of the Key Factors Influencing the Host-Guest Interactions

et al. 2022

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Sulfur mustard (SM) is a harmful warfare agent that poses a serious threat to human health and the environment. Thus, the design of porous materials capable of sensing and/or capturing SM is of utmost importance. In this paper, the interactions of SM and its derivatives with ethylpillar[5]arene (EtP[5]) and the interactions between SM and a variety of host macrocycles were investigated through molecular docking calculations and non-covalent interaction (NCI) analysis. The electronic quantum parameters were computed to assess the chemical sensing properties of the studied hosts toward SM. It was found that dispersion interactions contributed significantly to the overall complexation energy, leading to the stabilization of the investigated systems. DFT energy computations showed that SM was more efficiently complexed with DCMP[5] than the other hosts studied here. Furthermore, the studied macrocyclic containers could be used as host-based chemical sensors or receptors for SM. These findings could motivate experimenters to design efficient sensing and capturing materials for the detection of SM and its derivatives.

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Section: Introductionmentioning

confidence: 99%

In Search of Preferential Macrocyclic Hosts for Sulfur Mustard Sensing and Recognition: A Computational Investigation through the New Composite Method r2SCAN-3c of the Key Factors Influencing the Host-Guest Interactions

et al. 2022

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“…In addition, an unconventional lp··· π contact is also observed in one of the dimers of 2 . These noncovalent interactions play a critical role in the synthesis and stabilization of supramolecular architectures of numerous organic and inorganic compounds relevant to medicine, materials science, and catalysis …”

Section: Introductionmentioning

confidence: 99%

“…The crystal structure of These noncovalent interactions play a critical role in the synthesis and stabilization of supramolecular architectures of numerous organic and inorganic compounds relevant to medicine, materials science, and catalysis. 39 It is known that two cyclooxygenase (COX-1 and COX-2) enzymes have been involved in the inflammatory cell signaling pathway in an arachidonic acid-dependent manner. Selective inhibition of COX-2 can reduce the adverse reactions, including ulcerogenic effects of non-steroidal anti-inflammatory drugs such as acetylsalicylic acid and ibuprofen.…”

Section: Introductionmentioning

confidence: 99%

Structural and Energetic Properties of Weak Noncovalent Interactions in Two Closely Related 3,6-Disubstituted-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives: In Vitro Cyclooxygenase Activity, Crystallography, and Computational Investigations

et al. 2022

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Two 3,6-disubstituted-[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazole derivatives, namely, 3-(adamantan-1-yl)-6-(2-chloro-6-fluorophenyl)-[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazole 1 and 6-(2-chloro-6-fluorophenyl)-3-phenyl-[1,2,4]triazolo[3,4- b ][1,3,4]thiadiazole 2 , were prepared, and the detailed analysis of the weak intermolecular interactions responsible for the supramolecular self-assembly was performed using X-ray diffraction and theoretical tools. Analyses of Hirshfeld surface and 2D fingerprint plot demonstrated the effect of adamant-1-yl/phenyl moieties on intermolecular interactions in solid-state structures. The effect of these substituents on H···H/Cl/N contacts was more specific. The CLP-PIXEL and density functional theory methods provide information on the energetics of molecular dimers observed in these compounds. The crystal structure of compound 1 stabilizes with a variety of weak intermolecular interactions, including C–H···N, C–H···π, and C–H···Cl hydrogen bonds, a directional C–S···π chalcogen bond, and unconventional short F···C/N contacts. The crystal structure of compound 2 is stabilized by π-stacking interactions, C–H···N, C–H···π, and C–H···Cl hydrogen bonds, and highly directional attractive σ–hole interactions such as the C–Cl···N halogen bond and the C–S···N chalcogen bond. In addition, S(lp)···C(π) and short N···N contacts play a supportive role in the stabilization of certain molecular dimers. The final supramolecular architectures resulting from the combination of different intermolecular interactions are observed in both the crystal packing. The molecular electrostatic potential map reveals complementary electrostatic potentials of the interacting atoms. The quantum theory of atoms in molecules approach was used to delineate the nature and strength of different intermolecular interactions present in different dimers of compounds 1 and 2 . The in vitro experiments suggest that both compounds showed selectivity against COX-2 targets rather than COX-1. Molecular docking analysis showed the binding pose of the compounds at the active sites of COX-1/2 enzymes.

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“…With the surging interest in controlling molecular aggregations, , noncovalent interactions (NCIs) have been regarded as driving forces in defining and ruling organizations that lead to a wide variety of conformational architectures and thereafter govern the dynamic processes occurring within superstructures. , In particular, π–π stacking between aromatic rings are common motifs in biomolecular structures and also help understand the binding mechanism between the DNA and proteins, , stereoselective organic reactivity, catalyst design, and the stabilization of supramolecular complexes …”

mentioning

confidence: 99%

“…W ith the surging interest in controlling molecular aggregations, 1,2 noncovalent interactions (NCIs) have been regarded as driving forces in defining and ruling organizations that lead to a wide variety of conformational architectures and thereafter govern the dynamic processes occurring within superstructures. 3,4 In particular, π−π stacking between aromatic rings are common motifs in biomolecular structures and also help understand the binding mechanism between the DNA and proteins, 5,6 stereoselective organic reactivity, 7 catalyst design, 8 and the stabilization of supramolecular complexes. 9 Despite its frequent occurrence, picturing the nature of the π−π stacking remains challenging, since it is defined by a subtle balance between competing energetic contributions and is generally contaminated by other types of NCIs (e.g., hydrogen bonds (HBs), 10 halogen bonds 11 ).…”

mentioning

confidence: 99%

Scissor-like Face to Face π–π Stacking: A Surprising Preference Induced by the Isocyano Group in the Self-Assembled Dimer of Phenyl Isocyanide

Zheng

Wang

et al. 2022

J. Phys. Chem. Lett.

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Phenyl isocyanide has been chosen as a prototype to probe the π–π interaction modulated by the −NC group, which has a chameleonic nature with two main resonance forms showing a triple bond and being carbenoid. The rotational spectroscopic investigation complemented with theoretical analyses indicates that the phenyl isocyanide dimer has a scissor-like configuration controlled by dispersive forces along with the formation of π–π stacking. This is the first rotational spectroscopic evidence, to the best of our knowledge, that the mono-substitution by an −NC group on benzene can activate the meta position in forming noncovalent interactions. This work also provides experimental evidence on the importance of substituent effects in modulating π–π stacked structures, as well as practical proof of a biased interaction behavior of isocyanide-substituted aromatic molecules.

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Non-Covalent Interactions in Organic, Organometallic, and Inorganic Supramolecular Systems Relevant for Medicine, Materials Science, and Catalysis

Cited by 17 publications

References 21 publications

In Search of Preferential Macrocyclic Hosts for Sulfur Mustard Sensing and Recognition: A Computational Investigation through the New Composite Method r2SCAN-3c of the Key Factors Influencing the Host-Guest Interactions

In Search of Preferential Macrocyclic Hosts for Sulfur Mustard Sensing and Recognition: A Computational Investigation through the New Composite Method r2SCAN-3c of the Key Factors Influencing the Host-Guest Interactions

Structural and Energetic Properties of Weak Noncovalent Interactions in Two Closely Related 3,6-Disubstituted-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives: In Vitro Cyclooxygenase Activity, Crystallography, and Computational Investigations

Scissor-like Face to Face π–π Stacking: A Surprising Preference Induced by the Isocyano Group in the Self-Assembled Dimer of Phenyl Isocyanide

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