Halogen Bonding: A Halogen-Centered Noncovalent Interaction Yet to Be Understood
Abstract
:1. Introduction
2. Geometry-Based Identification of Halogen Bonding
2.1. Early Recognition
2.2. The Birth of Halogen Bonding and the σ-Hole Concept
2.3. Classification of Halogen Bonding
2.4. The Many-fold Controversy
2.4.1. Is an Atom–Atom Contact a Bond (or an Interaction)?
2.4.2. How to Define a Bond?
2.4.3. Is the Concept of Atomic Charge Meaningful?
2.4.4. Is the Directionality Feature in Halogen-Centered Noncovalent Interactions Understood?
2.4.5. Polarization Induced σ-Hole: Is It Real or a Provocation?
2.4.6. Is the σ-Hole Model a Unified Model?
2.5. The Topology of Fluorine Centered Bonding
2.6. The X3 Synthon in Crystals
3. Charge Density Models for Visualizing Noncovalent Interactions
4. Prototypical Examples of Halogen-Centered Noncovalent Interactions
4.1. The Tetrafluoromethane (CF4) System
4.2. The Tetrachloromethane (CCl4) System
4.3. The Tetrabromomethane (CBr4) System
4.4. The Tetraiodomethane (CI4) System
4.5. The Chlorine Monofluoride (ClF) Crystal System
4.6. Examples of Some Crystal Systems Stabilized by Type-I and -II Contacts
4.6.1. Some Halogen-Substituted Fullerene Systems
4.6.2. Some Halogen-Substituted Borane Systems
4.6.3. Some Halogen-Substituted Aromatic and Nonaromatic Systems
5. Conclusions and Outlook
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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0.0010 | 0.0015 | 0.00165 | 0.0017 | 0.0018 | 0.0020 | 0.0025 | 0.0030 | 0.0035 | 0.0040 | 0.0050 | 0.0055 |
- a | - a | −3.72 | −3.70 | −3.64 | −3.50 | −3.10 | −2.60 | −2.10 | −1.52 | −0.25 | +0.41 |
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Varadwaj, P.R.; Varadwaj, A.; Marques, H.M. Halogen Bonding: A Halogen-Centered Noncovalent Interaction Yet to Be Understood. Inorganics 2019, 7, 40. https://doi.org/10.3390/inorganics7030040
Varadwaj PR, Varadwaj A, Marques HM. Halogen Bonding: A Halogen-Centered Noncovalent Interaction Yet to Be Understood. Inorganics. 2019; 7(3):40. https://doi.org/10.3390/inorganics7030040
Chicago/Turabian StyleVaradwaj, Pradeep R., Arpita Varadwaj, and Helder M. Marques. 2019. "Halogen Bonding: A Halogen-Centered Noncovalent Interaction Yet to Be Understood" Inorganics 7, no. 3: 40. https://doi.org/10.3390/inorganics7030040