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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

16.8K
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...
16.8K
Halogenation of Alkenes02:46

Halogenation of Alkenes

17.1K
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.
17.1K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.6K
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.
12.6K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.5K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.5K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
10.3K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.0K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.0K

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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3-[1-(4-Bromo-phen-yl)eth-oxy]-2,2,5-trimethyl-4-phenyl-3-aza-hexa-ne.

Praveen Pitliya1, Ray J Butcher1, A Karim2

  • 1Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
PubMed
Summary
This summary is machine-generated.

This study details a novel alk-oxy-amine compound, C22H30BrNO, an effective initiator for nitroxide-mediated free radical polymerization. X-ray analysis revealed its diastereomeric mixture and specific molecular conformations, including disordered bromine atom positions.

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Nitroxide-mediated polymerization (NMP) is a controlled radical polymerization technique.
  • Alkoxyamine compounds are crucial initiators in NMP.
  • Developing new initiators with specific structural features is essential for advancing NMP.

Purpose of the Study:

  • To synthesize and characterize a novel alkoxyamine compound, C22H30BrNO.
  • To elucidate the crystal structure and conformational properties of the compound using X-ray diffraction.
  • To assess its potential as an initiator in nitroxide-mediated free radical polymerization.

Main Methods:

  • Synthesis of the title alkoxyamine compound.
  • Single crystal X-ray diffraction analysis.
  • Analysis of molecular conformation and intermolecular interactions.

Main Results:

  • The compound C22H30BrNO was prepared as a mixture of two diastereomers.
  • X-ray analysis confirmed the presence of one diastereomer as a pair of enantiomers (R,S and S,R).
  • Specific conformations of tert-butyl, isopropyl, and ethoxy groups were determined, along with a dihedral angle of 33.12° between phenyl rings. The bromine atom exhibited disorder over two positions.

Conclusions:

  • The synthesized alk-oxy-amine compound possesses defined structural characteristics suitable for polymerization initiation.
  • The crystal structure provides insights into the conformational preferences and packing of such molecules.
  • Further studies are warranted to explore its efficacy in nitroxide-mediated free radical polymerization.