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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

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:
¹H NMR: Complex Splitting01:13

¹H NMR: Complex Splitting

A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied first.
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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The magic triangle goes MAD: experimental phasing with a bromine derivative.

Tobias Beck1, Tim Gruene, George M Sheldrick

  • 1Department of Structural Chemistry, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany. tbeck@shelx.uni-ac.gwdg.de

Acta Crystallographica. Section D, Biological Crystallography
|April 13, 2010
PubMed
Summary

A new phasing tool, 5-amino-2,4,6-tribromoisophthalic acid (B3C), offers improved protein binding for macromolecular structure determination. This novel compound enables successful multiwavelength anomalous dispersion (MAD) experiments.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Area of Science:

  • Structural Biology
  • Biochemistry
  • Crystallography

Background:

  • Macromolecular structure determination relies on experimental phasing.
  • Nonspecific binding of heavy-atom ions is a common challenge in phasing.
  • Novel compounds combining heavy atoms and functional groups are needed for specific protein binding.

Purpose of the Study:

  • To develop and evaluate a novel phasing tool, 5-amino-2,4,6-tribromoisophthalic acid (B3C).
  • To assess B3C's efficacy in multiwavelength anomalous dispersion (MAD) experiments.
  • To investigate radiation damage and compare B3C with existing phasing tools.

Main Methods:

  • Synthesis of 5-amino-2,4,6-tribromoisophthalic acid (B3C).
  • Incorporation of B3C into proteinase K.
  • Conducting multiwavelength anomalous dispersion (MAD) experiments at the Br K edge.
  • Investigating radiation damage to the bromine-carbon bond.

Main Results:

  • B3C demonstrated effective binding to proteins via hydrogen bonds through its functional groups.
  • Successful MAD phasing experiment was carried out using B3C.
  • Radiation damage to the B3C bromine-carbon bond was investigated.
  • Comparison with I3C for single-wavelength anomalous dispersion (SAD) phasing was performed.

Conclusions:

  • B3C is a promising novel phasing tool for macromolecular crystallography.
  • The compound's design facilitates specific protein interactions and efficient phasing.
  • B3C offers a viable alternative for experimental phasing, particularly in MAD experiments.