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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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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.
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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.
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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...
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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...
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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution.

Martin H H Voelkel1, Patrick Wonner1, Stefan Matthias Huber1

  • 1Fakultät für Chemie und Biochemie Ruhr-Universität Bochum Universitätsstraße 150 44801 Bochum Germany.

Chemistryopen
|February 20, 2020
PubMed
Summary
This summary is machine-generated.

Preorganization significantly enhances halogen bonding strength in supramolecular chemistry. This study confirms preorganization, not electronic effects, drives increased Lewis acidity in bis(iodobenzimidazolium) catalysts.

Keywords:
Lewis acidsanion recognitionhalogen bondingorganocatalysissolution

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Catalysis

Background:

  • Halogen bonding is a key interaction in supramolecular chemistry.
  • Previous work developed a trifluoromethyl-substituted bis(iodobenzimidazolium) halogen bond donor with enhanced catalytic activity.
  • The enhanced activity was potentially due to electronic effects or preorganization.

Purpose of the Study:

  • To systematically investigate the origin of increased Lewis acidity in halogen bond donors.
  • To differentiate the contributions of electronic effects versus preorganization.
  • To compare trifluoromethyl-substituted and unsubstituted bis(iodobenzimidazolium) compounds.

Main Methods:

  • Synthesis of bis(iodobenzimidazolium) derivatives with and without a trifluoromethyl group.
  • Calorimetric measurements of halide complexations to quantify halogen bonding strength.
  • Evaluation of catalyst performance in benchmark chemical reactions.

Main Results:

  • Calorimetric data revealed that preorganization is the primary factor responsible for increased halogen bonding strength.
  • The trifluoromethyl group's influence on electronic effects was less significant than preorganization.
  • Catalytic performance in benchmark reactions aligned with findings on halogen bonding strength.

Conclusions:

  • Preorganization, achieved through structural design, is the dominant factor enhancing Lewis acidity and halogen bonding strength.
  • The study clarifies the mechanism behind the improved catalytic activity of the developed halogen bond donors.
  • This research provides insights for designing more effective supramolecular catalysts.