Related Experiment Video
Updated: Dec 6, 2025
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Nature and Strength of Lewis Acid/Base Interaction in Boron and Nitrogen Trihalides
Daniela Rodrigues Silva1,2, Lucas de Azevedo Santos1,2, Matheus P Freitas2
1Department of Theoretical Chemistry, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Amsterdam Center for Multiscale Modeling (ACMM), Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV, Amsterdam (The, Netherlands.
Abstract:
We have quantum chemically investigated the bonding between archetypical Lewis acids and bases. Our state-of-the-art computations on the X3 B-NY3 Lewis pairs have revealed the origin behind the systematic increase in B-N bond strength as X and Y are varied from F to Cl, Br, I, H. For H3 B-NY3 , the bonding trend is driven by the commonly accepted mechanism of donor-acceptor [HOMO(base)-LUMO(acid)] interaction. Interestingly, for X3 B-NH3 , the bonding mechanism is determined by the energy required to deform the BX3 to the pyramidal geometry it adopts in the adduct. Thus, Lewis acids that can more easily pyramidalize form stronger bonds with Lewis bases. The decrease in the strain energy of pyramidalization on going from BF3 to BI3 is directly caused by the weakening of the B-X bond strength, which stems primarily from the bonding in the plane of the molecule (σ-like) and not in the π system, at variance with the currently accepted mechanism.
Related Concept Videos
02:16Lewis Acids and Bases
02:33Lewis Acids and Bases
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
02:55Exceptions to the Octet Rule
02:45Alkyl 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...
03:05Acid Strength and Molecular Structure
In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals (A) increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te. Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with increasing...
03:13Intermolecular Forces