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Related Concept Videos

Halogens03:01

Halogens

18.3K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Valence Bond Theory02:45

Valence Bond Theory

31.9K
Overview of Valence Bond Theory
31.9K
Alkyl Halides02:45

Alkyl Halides

16.3K
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...
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Intermolecular Forces03:13

Intermolecular Forces

57.7K
Atoms and molecules interact through bonds (or forces): intramolecular and intermolecular. The forces are electrostatic as they arise from interactions (attractive or repulsive) between charged species (permanent, partial, or temporary charges) and exist with varying strengths between ions, polar, nonpolar, and neutral molecules. The different types of intermolecular forces are ion–dipole, dipole–dipole, hydrogen bonds, and dispersion; among these, dipole–dipole, hydrogen...
57.7K
Intermolecular vs Intramolecular Forces03:00

Intermolecular vs Intramolecular Forces

86.6K
Intermolecular forces (IMF) are electrostatic attractions arising from charge-charge interactions between molecules. The strength of the intermolecular force is influenced by the distance of separation between molecules. The forces significantly affect the interactions in solids and liquids, where the molecules are close together. In gases, IMFs become important only under high-pressure conditions (due to the proximity of gas molecules). Intermolecular forces dictate the physical properties of...
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Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

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The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
3.7K

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Related Experiment Video

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

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Modulating the Competition between Different Atoms to Form Halogen Bonds.

Steve Scheiner1

  • 1Department of Chemistry and Biochemistry, Utah State University, Logan, Utah 84322-0300, United States.

The Journal of Physical Chemistry. A
|November 11, 2024
PubMed
Summary

Substituents on alkyl chains can reverse halogen bonding preferences between iodine and bromine atoms. This control is more challenging with aromatic rings due to electron cloud mobility.

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Area of Science:

  • Computational chemistry
  • Supramolecular chemistry
  • Organic chemistry

Background:

  • Halogen bonding (XB) is a non-covalent interaction involving a Lewis base and an electrophilic halogen atom.
  • The strength of halogen bonds typically correlates with halogen size and polarizability, with larger halogens like iodine forming stronger bonds than bromine.
  • Controlling the selectivity and strength of halogen bonds is crucial for designing molecular recognition and self-assembly systems.

Purpose of the Study:

  • To investigate the influence of substituent placement on alkyl chains on halogen bond donor selectivity.
  • To explore the feasibility of reversing the intrinsic halogen bond preference between iodine and bromine.
  • To compare the effect of substituents on alkyl chains versus aromatic rings in modulating halogen bond interactions.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to model halogen bonding interactions.
  • The study focused on systems involving iodine (I) and bromine (Br) atoms as halogen bond donors and ammonia (NH3) as a nucleophile.
  • Substituent effects on n-butyl chains and aromatic rings were systematically analyzed.

Main Results:

  • DFT calculations revealed that the intrinsic preference for iodine over bromine as a halogen bond donor can be reversed by strategic substituent placement on an n-butyl chain.
  • Similar reversals in donor strength were observed for oxygen (O) versus nitrogen (N) atoms in substituents interacting with electrophilic iodine.
  • Reversing these preferences was found to be significantly more challenging when the competing halogen atoms were part of an aromatic system, attributed to the mobile pi-electron cloud.

Conclusions:

  • Substituent engineering on alkyl chains offers a viable strategy to tune and reverse halogen bond donor selectivity.
  • The electronic environment, particularly the presence of electron-donating or withdrawing groups, plays a critical role in modulating halogen bond strength and selectivity.
  • Aromatic systems present inherent challenges for achieving such reversals due to their delocalized electronic structure, impacting the fine-tuning of halogen bonding interactions.