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Halogenation of Alkenes02:46

Halogenation of Alkenes

20.7K
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.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

18.1K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
18.1K
Alkyl Halides02:45

Alkyl Halides

21.0K
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...
21.0K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

7.1K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
7.1K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

15.0K
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.
15.0K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.7K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
4.7K

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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A single heteroatom controls halogen- versus chalcogen-bond-driven cellular uptake.

Debasish Giri1, Ekta Chauhan1, Govindasamy Mugesh1

  • 1Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India. mugesh@iisc.ac.in.

Chemical Communications (Cambridge, England)
|March 13, 2026
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Summary

This study reveals how halogen and chalcogen bonds influence membrane interactions. Oxygen-based molecules use halogen bonding, while sulfur and selenium molecules rely on chalcogen bonding for uptake.

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Area of Science:

  • Supramolecular chemistry
  • Chemical biology

Background:

  • Halogen bonds and chalcogen bonds are non-covalent interactions that can mediate molecular recognition.
  • These interactions play roles in biological systems, including membrane interactions.

Purpose of the Study:

  • To investigate the distinct roles of halogen and chalcogen bonding in membrane recognition within a single molecular scaffold.
  • To compare the uptake mechanisms of oxygen, sulfur, and selenium analogues.

Main Methods:

  • Synthesis of molecular scaffolds containing oxygen, sulfur, and selenium analogues.
  • Assays to measure membrane recognition and uptake.
  • Spectroscopic and computational analyses to probe bonding interactions.

Main Results:

  • Oxygen analogues demonstrated uptake primarily dependent on halogen bonding.
  • Sulfur and selenium analogues showed uptake predominantly mediated by chalcogen bonding.
  • The same scaffold exhibited differential recognition based on the chalcogen atom.

Conclusions:

  • Halogen and chalcogen bonds play distinct, complementary roles in membrane recognition.
  • The nature of the chalcogen atom dictates whether halogen or chalcogen bonding dominates membrane interactions.
  • This provides a basis for designing molecules with tailored membrane recognition properties.