Enhancement of Iodine–Hydride Interaction by Substitution and Cooperative Effects in NCX–NCI–HMY Complexes

Li, Qingzhong; Sun, Liang; Liu, Xiaofeng; Li, Wenzuo; Cheng, Jianbo; Zeng, Yanli

doi:10.1002/cphc.201200430

Cited by 22 publications

(12 citation statements)

References 57 publications

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“…Due to the similarity between halogen and hydrogen bonds, the halogen bond also exhibits cooperative effects with itself and other types of interactions [3,33,[35][36][37]. More recently, the cooperative effects in the 4-Z-Py···XCN···XCN system (Z=H, F, OH, OCH 3 , CH 3 , NH 2 , NO 2 , and CN; Py = pyridine; and X = Cl and Br) was reported [38].…”

Section: Introductionmentioning

confidence: 92%

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Cooperativity between fluorine-centered halogen bonds: investigation of substituent effects

et al. 2013

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This article analyzes the substitution effects on cooperativity between fluorin-centered halogen bonds in NCF · · · NCF · · · NCX and CNF · · · CNF · · · CNX complexes, where X = H, F, Cl, CN, OH, and NH₂. These effects are investigated theoretically in terms of geometric and energetic features of the complexes, which are computed by ab initio methods. The topological analysis, based on the quantum theory of atoms in molecules (QTAIM), is used to characterize the interactions and analyze their enhancement with varying electron density at bond critical points. It is found that the complexes with electron-donating groups exhibit a strong cooperativity, while a much weaker cooperativity occurs in the NCF · · · NCF · · · NCCN and CNF · · · CNF · · · CNCN trimers. An excellent correlation is found between the cooperative energy in the ternary complexes and the calculated three-body interaction energies. The energy decomposition analysis (EDA) indicates that the electrostatic and dispersion effects play a main role in the cooperativity of fluorine-centered halogen bonding.

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Section: Introductionmentioning

confidence: 92%

“…The cooperativity is one of the most important characteristics of non-covalent interactions [33,34]. Due to the similarity between halogen and hydrogen bonds, the halogen bond also exhibits cooperative effects with itself and other types of interactions [3,33,[35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Cooperativity between fluorine-centered halogen bonds: investigation of substituent effects

et al. 2013

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“…This deviation was found for the H-M-Li and H-M-Na (M = Be and Mg) in halogen-hydride interactions with ICN as the halogen donor. 62 The relative magnitude of molecule XO 2 F geometrical deformation can be estimated with the change of F-X···N/C angle. This angle becomes larger in the XO 2 F:HNC complex than that in the HCN counterpart, and the substituent Li makes it much larger.…”

Section: Theoretical Methodsmentioning

confidence: 99%

Non-additivity between substitution and cooperative effects in enhancing hydrogen bonds

Zhuo

Cheng

2014

The Journal of Chemical Physics

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Ternary systems XO2F:NCH:NCY and XO2F:CNH:CNY (X = P and As; Y = H and Li) as well as the corresponding binary ones were studied at the MP2/aug-cc-pVTZ level. Interestingly, the π-hole pnicogen bond in the PO2F complex is stronger than that in the AsO2F counterpart. The substituent Li in the Lewis base strengthens the hydrogen bond and pnicogen bond, but the more prominent enhancing effect is found for the pnicogen bond. The substitution effect is governed mainly through electrostatic interaction for the hydrogen bond but a combination of electrostatic and polarization interactions for the pnicogen bond. In the ternary systems, the π-hole pnicogen bond exhibits a positive cooperative effect with the hydrogen bond. Energy decomposition analysis indicates that the cooperativity is mainly attributed to the polarization energy. There is positive non-additivity between the substitution and cooperative effects, which is an effective measure for strengthening the hydrogen bond. The largest interaction energies occur in AsO2F:CNH:CNLi, amounting to -130.24 kJ/mol for the pnicogen bond and -119.90 kJ/mol for the hydrogen bond, and the former is a covalent interaction and the latter is an ion-pair hydrogen bond.

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“…In complex systems with the presence of two or more non-covalent interactions, there is a mutual interplay between them, irrespective of whether they are of the same type [36,37] or different [38][39][40]. This mutual influence can lead to interesting cooperativity or synergic effects.…”

Section: Introductionmentioning

confidence: 97%

Effect of cation–π interaction on lithium and halogen bonds: a comparative study

Esrafili

Mohammadirad

2014

Molecular Physics

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Ab initio calculations have been performed to study the complex of M + -PhX-NCY (M = Li, Na; X = Li, Br and Y = H, OH and NH 2 ). The aim is to compare the mutual cooperative effects between cation-π and lithium/halogen interactions. These effects are studied in terms of geometric and energetic properties, 15 N chemical shielding parameters, molecular electrostatic potentials and natural bond orbital analyses. A positive cooperativity is observed on introduction of a cation-π interaction to the PhLi-NCY and PhBr-NCY dyads. The cation-π interaction has an enhancing effect on the halogen bond interaction energy, making it increased by152%-233%, whereas that of lithium bond interaction by 18%-22%. The enhancing mechanism is analysed in views with the atomic charges, charge transfer and electrostatic potentials.

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Enhancement of Iodine–Hydride Interaction by Substitution and Cooperative Effects in NCX–NCI–HMY Complexes

Cited by 22 publications

References 57 publications

Cooperativity between fluorine-centered halogen bonds: investigation of substituent effects

Cooperativity between fluorine-centered halogen bonds: investigation of substituent effects

Non-additivity between substitution and cooperative effects in enhancing hydrogen bonds

Effect of cation–π interaction on lithium and halogen bonds: a comparative study

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