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Hydrogen Bonds

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...

Hydrogen Bonds

Hydrogen Bonds

Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....

Alkyl Halides

Alkyl Halides

Structural Properties
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...

Valence Bond Theory

Valence Bond Theory

Overview of Valence Bond Theory

Valence Bond Theory

Valence Bond Theory

Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...

Noncovalent Attractions in Biomolecules

Noncovalent Attractions in Biomolecules

Noncovalent attractions are associations within and between molecules that influence the shape and structural stability of complexes. These interactions differ from covalent bonding in that they do not involve sharing of electrons.
Four types of noncovalent interactions are hydrogen bonds, van der Waals forces, ionic bonds, and hydrophobic interactions.
Hydrogen bonding results from the electrostatic attraction of a hydrogen atom covalently bonded to a strong-electronegative atom like oxygen,...

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Related Experiment Video

Updated: Nov 1, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Halogen-Halogen Nonbonded Interactions.

Kenneth B Wiberg¹

¹Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.

|June 21, 2021

Summary

This summary is machine-generated.

Halogen bonding interactions in methyl and phenyl halides show minimal stabilization via direct halogen-halogen contact. Instead, halogen-hydrogen interactions and substituted ring orientations significantly influence molecular arrangements and crystal structures.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

Computational Chemistry
Chemical Physics
Molecular Interactions

Background:

Nonbonded interactions are crucial for molecular assembly and material properties.
Halogen bonding, a specific type of nonbonded interaction, plays a significant role in crystal engineering and supramolecular chemistry.

Purpose of the Study:

To investigate halogen-halogen nonbonded interactions in methyl halides and phenyl halides.
To determine the energetic contributions of different interaction geometries and types (halogen-halogen vs. halogen-hydrogen).

Main Methods:

Utilized computational chemistry methods, specifically B3LYP and MP2 levels of theory.
Employed extended basis sets, including 6-311+G* and aug-cc-pVTZ, for accurate electronic structure calculations.

Main Results:

Methyl halides exhibit modest stabilization (1-2 kcal/mol) through "90°" approaches, attributed to long-range electron correlation.
Halogen-hydrogen interactions were found to be a major stabilizing factor in methyl halide dimers.
Chlorobenzene dimers showed greater stabilization when benzene rings were stacked, with meta-oriented chlorine atoms being energetically favorable over ortho or para.
Dimerization energies suggest halogen-halogen interactions are less significant than the influence of halogens on electron distribution and ring-ring interactions.

Conclusions:

Direct halogen-halogen interactions contribute minimally to the stabilization of methyl and phenyl halide dimers.
Halogen-hydrogen interactions and pi-stacking of aromatic rings are more dominant forces in determining molecular arrangements.
Crystallographic observations in these compounds may be primarily driven by substituted ring interactions and crystal packing forces, rather than direct halogen-halogen contacts.