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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

15.7K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
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.
15.7K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.9K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
12.9K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.1K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.1K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.5K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.5K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.2K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.2K
VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

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Effect of Lone Pairs of Electrons on Molecule Geometry
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Bromination of 2D materials.

Eva Marie Freiberger1, Julien Steffen2, Natalie J Waleska-Wellnhofer1

  • 1Physikalische Chemie II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstr. 3, D-91058 Erlangen, Germany.

Nanotechnology
|December 4, 2023
PubMed
Summary

Bromine adsorption on hexagonal boron nitride (h-BN) nanomesh and graphene reveals distinct behaviors. Bromine reacts on h-BN but not graphene, indicating selective surface interactions and potential for novel material applications.

Keywords:
brominefunctionalizationgraphenehexagonal boron nitridemachine-learning force fieldmolecular dynamicsx-ray photoelectron spectroscopy

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Area of Science:

  • Surface Science
  • Materials Chemistry
  • Nanotechnology

Background:

  • Hexagonal boron nitride (h-BN) and graphene are 2D materials with unique electronic properties.
  • Understanding halogen interactions with these surfaces is crucial for catalysis and electronics.

Purpose of the Study:

  • Investigate bromine adsorption, reaction, and thermal stability on h-BN/Rh(111) and graphene/Rh(111).
  • Compare the reactivity and bonding characteristics of bromine on these distinct 2D materials.

Main Methods:

  • High-resolution X-ray Photoelectron Spectroscopy (XPS) and temperature-programmed XPS for in situ analysis.
  • Density Functional Theory (DFT) calculations for theoretical support.
  • Molecular dynamics simulations with a machine-learning force field.

Main Results:

  • Bromine selectively adsorbs within h-BN nanomesh pores, unlike on graphene.
  • On-surface reactions form polybromides on h-BN, followed by decomposition to bromide, indicating strong covalent bonding.
  • Bromine shows limited reactivity on graphene, with some intercalation at high temperatures.
  • Adsorption is reversible on both surfaces upon heating.

Conclusions:

  • The h-BN nanomesh exhibits selective bromine adsorption and unique reactivity compared to graphene.
  • Strong covalent bonding of bromine to h-BN suggests potential for stable functionalization.
  • Theoretical calculations support experimental findings on adsorption energetics and substrate interactions.