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Halogenation of Alkenes02:46

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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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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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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.
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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pH controlled assembly of a self-complementary halogen-bonded dimer.

Leonardo Maugeri1, Ellen M G Jamieson1, David B Cordes1

  • 1School of Chemistry and EaStCHEM , University of St Andrews , North Haugh , St Andrews , Fife KY16 9ST , UK . Email: d.philp@st-andrews.ac.uk ; ; Tel: +44 1334 467264.

Chemical Science
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Summary
This summary is machine-generated.

Phenols and phenoxide anions form halogen bonds with iodotriazoles. Deprotonation triggers self-assembly into stable, reversible dimers, demonstrating tunable molecular interactions.

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Area of Science:

  • Supramolecular Chemistry
  • Halogen Bonding
  • Molecular Recognition

Background:

  • Halogen bonds are crucial non-covalent interactions.
  • The strength of halogen bonds is sensitive to the electronic environment of the interacting atoms.
  • Protonation state significantly influences the interaction strength between phenols/phenoxides and halogen bond donors.

Purpose of the Study:

  • To investigate halogen bonding between phenols/phenoxide anions and iodotriazoles.
  • To demonstrate self-assembly of molecules through halogen bonding.
  • To explore the influence of protonation state on molecular assembly and its reversibility.

Main Methods:

  • Synthesis of molecules containing both iodotriazole and phenol/phenoxide moieties.
  • X-ray crystallography for solid-state structure determination.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (specifically 19F NMR) for solution-state analysis and stability studies.

Main Results:

  • Phenoxide anions form significantly stronger halogen bonds with iodotriazoles compared to phenols.
  • A molecule bearing both an iodotriazole and a phenoxide anion self-assembles into a stable homodimer via halogen bonds.
  • The assembly process is triggered by deprotonation (addition of base) and is fully reversible upon protonation.
  • The dimer structure was confirmed in the solid state and its persistence and stability in solution were demonstrated using 19F NMR.

Conclusions:

  • The protonation state of oxygen atoms critically controls halogen bond-mediated assembly.
  • Tunable and reversible self-assembly of molecular systems can be achieved by modulating protonation states.
  • This work highlights the potential of halogen bonding in designing responsive supramolecular structures.