Related Experiment Video
Updated: Nov 20, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
A low cost, high accuracy method for halogen bonding complexes
Raphaël Robidas1, Claude Y Legault1, Stefan M Huber2
1Department of Chemistry, Université de Sherbrooke, 2500 boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada. Raphael.Robidas@USherbrooke.ca.
Abstract:
The ONIOM scheme M052X/[Def2TZVP+Def2TZVPD.ECP(I)]:AM1 is shown to represent halogen bond (XB) geometries nearly as well as DFT while being more than two orders of magnitude faster in systems containing >40 atoms. This finding is shown to hold for 40 XB donors, which cover most known backbones, and for a range of neutral and anionic Lewis bases. Complexation free energies can be accurately computed using these geometries and a single-point energy calculation at the DFT level. This approach circumvents the unfavorable scaling of computing time associated with modeling large systems involving halogen bonding.
More Related Videos
Related Concept Videos
Alkyl Halides
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Multiple Halogenation of Methyl Ketones: Haloform Reaction
α-Halogenation of Carboxylic Acid Derivatives: Overview
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Hybridization of Atomic Orbitals I

