Can the positive aromatic ring be as π-electron donor in π-halogen bond? A MP2 theoretical investigation on the unusual π-halogen bond interaction between three-membered ring $$ \left( {\hbox{BNN}} \right)_3^{+} $$ and X1X2 (X1, X2 = F, Cl, Br)

Qi, Haitao; Ren, Fangfang; Zhang, Jing-lin; Wang, Jingyu

doi:10.1007/s00894-010-0790-9

Cited by 7 publications

(3 citation statements)

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“…Even less common are XB interactions between non-carbon-based aromatic π-systems and halogen atoms. Qi et al studied the interactions between the electron-deficient positive aromatic three-membered ring (BNN) 3+ and dihalogen molecules XY employing MP2 calculations based on the 6-311+ G(2d) and aug-cc-pVDZ basis sets and found the calculated binding energies followed the expected trends in the dipole moment of the dihalogen, the polarizability of X, and the electron-withdrawing strength of Y . All-metal aromatic species such as Al 4 2– , initially described by Li et al, were also able to establish a π–XB interaction with halohydrocarbons (XCH 3 , XCH 2 CH 3 , XCHCH 2 , and XCCH, with X = Cl, Br, I) .…”

Section: Computational and Theoretical Investigations Of Halogen Bondingmentioning

confidence: 99%

“…Qi et al studied the interactions between the electron-deficient positive aromatic three-membered ring (BNN) 3+ molecules XY employing MP2 calculations based on the 6-311+ G(2d) and aug-cc-pVDZ basis sets and found the calculated binding energies followed the expected trends in the dipole moment of the dihalogen, the polarizability of X, and the electron-withdrawing strength of Y. 97 All-metal aromatic species such as Al 4 2−…”

Section: Other Contributions To the Nature Of Halogen Bondingmentioning

confidence: 99%

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Halogen Bonding in Supramolecular Chemistry

et al. 2015

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CONTENTS 1. Introduction to Halogen Bonding 7119 1.1. Nature of the Halogen Bond 7119 1.2. Scope of the Review 7120 2. Computational and Theoretical Investigations of Halogen Bonding 7120 2.1.Quantum Mechanics Methods 7120 2.2. σ-Hole Model of Halogen Bonding 7120 2.3. Other Contributions to the Nature of Halogen Bonding 7122 2.4. Recent Examples of Computationally Investigated Halogen-Bonded Complexes 7123 2.4.1. XB to Neutral Species 7123 2.4.2. XB to Anions 7126 2.4.3. XB in Protein−Ligand Complexes 7127 2.4.4. Electron-Transfer Processes Affected by XB Interactions 7127 2.5. Classical Force Field Calculations 7127 2.6. Conclusions and Outlook 7129 3. Gas-Phase Studies of Halogen-Bonding Interactions 7130 4. Halogen Bonding in the Solid State 7131 4.1. Introduction to Crystal Engineering and Functional Materials 7131 4.2. Fundamentals 7132 4.3. Halogen-Bonding Hierarchy 7134 4.3.1. Ranking Halogen-Bond Donors 7134 4.3.2. HB/XB Complementarity/Competition 7136 4.3.3. Predicting XBs 7138 4.4. Control of Solid-State Supramolecular Architectures 7138 4.4.1. Polymorphism 7138 4.4.2. Stoichiometry 7139 4.4.3. Tautomeric Control 7140 4.4.4. XBs Involving Metals and Metal-Bound XBs 7140 4.4.5. XB with Anions in the Solid State 4.5. Solid-State Architectures 4.6.

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Section: Computational and Theoretical Investigations Of Halogen Bondingmentioning

confidence: 99%

Section: Other Contributions To the Nature Of Halogen Bondingmentioning

confidence: 99%

Halogen Bonding in Supramolecular Chemistry

et al. 2015

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“…Therefore, the X•••π bonding in complex ii is more reasonable. However, due to the unusual X•••π bonding in complex ii 48 , we performed DFT calculations for it using M06-2X in 1,2-dichloroethane. The structure of complex ii (Fig.…”

Section: Resultsmentioning

confidence: 99%

Multiselective gridization achieved by electrophilic C-X activation of dual halogen bonding cooperation

Xie

Wei

Zhong

et al. 2022

Preprint

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Organic science & technology (OST) become the frontier horizon after nanotechnology, information technology as well as biotechnology toward the era of consciousness. Organic nanogridarenes (ONGAs) are becoming robust nanoscaffolds for next-generation multifunctional/intelligent semiconductors with tunable cross-scale features. However, the prerequisite of trans-dimensional & intelligent design is to clarify the gridization rules for the discovery of the powerful molecular gridization protocols. Here, we report an efficient and multiselective Csp2-Csp3 gridization based on dual halogen bonding (X···π and X···S, X = Br, I) self-activated electrophilic substitution of halogenated electron-rich molecular blocks under supersonic conditions. Windmill-type nanogrids of cyclopenta[1,2-b:5,4-b']dithiophene (WG4) were obtained with the maximum path selectivity (96%), nanogrid-size selectivity (67%), site-selectivity (>99%) and moderate diastereoselectivity (WG4-1-6:WG4-2-6:WG4-3-6:WG4-4-6 =1:3.3:5.3:0), superior to the previous Friedel-Crafts gridization. Mechanistic studies have revealed the roles of XBs where the X···S bonding accelerates dehalogenation after electrophilic attack, and the X···π bonding leads to the multiselectivity of WG4. Impressively, C2-symmetric WG4-1-6 (21×21×15 Å) crystallizes into a Fd3̄c space group as the 16th pure organic molecules in CCDC library and hierarchically self-assemble into a complex 3D porous superstructure.

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Is a MH (M = Be and Mg) radical a better electron donor in halogen‐hydride interaction?: A theoretical comparison with HMH

Bai

Cheng

et al. 2012

Int J of Quantum Chemistry

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Quantum chemical calculations have been performed to investigate the complexes of HMHXCCH, HMHXCF3, MHXCCH, and MHXCF3 (M = Be and Mg; X = Cl, Br, and I) at the MP2/aug‐cc‐pVTZ level. The geometrical, energetic, and spectroscopic parameters were analyzed for these complexes. The results show that the MH is a better electron donor in the halogen‐hydride interaction than HMH. The enhancement of halogen‐hydride interaction increases in the order of Cl < Br < I, Be < Mg, and XCCH < XCF3. The halogen‐hydride interaction was understood with natural bond orbital, atoms in molecules, and electrostatic potentials. © 2012 Wiley Periodicals, Inc.

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Can the positive aromatic ring be as π-electron donor in π-halogen bond? A MP2 theoretical investigation on the unusual π-halogen bond interaction between three-membered ring $$ \left( {\hbox{BNN}} \right)_3^{+} $$ and X1X2 (X1, X2 = F, Cl, Br)

Cited by 7 publications

References 51 publications

Halogen Bonding in Supramolecular Chemistry

Halogen Bonding in Supramolecular Chemistry

Multiselective gridization achieved by electrophilic C-X activation of dual halogen bonding cooperation

Is a MH (M = Be and Mg) radical a better electron donor in halogen‐hydride interaction?: A theoretical comparison with HMH

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