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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

18.6K
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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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

9.1K
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.
9.1K
Halogenation of Alkenes02:46

Halogenation of Alkenes

17.2K
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.
17.2K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.5K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
2.5K
Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

2.2K
The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
2.2K
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

2.2K
The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Cooperative Self-Assembly in Linear Chains Based on Halogen Bonds.

Pascal Vermeeren1, Lando P Wolters1, Gábor Paragi1,2,3

  • 1Department of Theoretical Chemistry, Amsterdam Institute of Molecular and Life Sciences (AIMMS) Amsterdam Center for Multiscale Modeling (ACMM), Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV, Amsterdam, The Netherlands.

Chempluschem
|April 27, 2021
PubMed
Summary
This summary is machine-generated.

Computational studies reveal cooperative halogen bonding in linear chains. This enhanced stability arises from charge transfer, similar to hydrogen bonds, particularly in cyanogen halide and halocyanoacetylene systems.

Keywords:
MO theorycooperativityenergy decomposition analysishalogen bondingnon-covalent interactions

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Supramolecular Chemistry

Background:

  • Halogen bonding is a significant non-covalent interaction.
  • Understanding cooperative effects in molecular chains is crucial for materials science.
  • Previous studies have explored halogen bonding but often focused on isolated interactions.

Purpose of the Study:

  • To investigate the cooperative properties of halogen bonds in linear molecular chains.
  • To elucidate the underlying bonding mechanism using advanced computational methods.
  • To compare the cooperativity in different types of halogen-containing systems.

Main Methods:

  • Dispersion-corrected relativistic density functional theory (DFT) calculations.
  • Energy decomposition analysis (EDA).
  • Kohn-Sham molecular orbital (KS-MO) analysis.

Main Results:

  • Linear chains of cyanogen halide (X-CN) and halocyanoacetylene (X-CC-CN) exhibit increased stabilization with chain length.
  • 4-halobenzonitrile (X-C6 H4 -CN) chains do not show significant cooperative effects.
  • The cooperativity is attributed to charge transfer between nitrogen lone-pair (σHOMO) and C-X acceptor (σ*LUMO) orbitals, decreasing the σ-system's HOMO-LUMO gap.

Conclusions:

  • Cooperative halogen bonding is confirmed in specific linear molecular architectures.
  • The observed cooperativity mechanism is analogous to that of hydrogen bonds.
  • These findings provide insights into the design of novel materials with tunable electronic properties.