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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.8K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.3K
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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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
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

10.3K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
10.3K
Alkyl Halides02:45

Alkyl Halides

19.3K
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...
19.3K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.0K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Related Experiment Video

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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3-Methyl-piperidinium bromide.

Qian Xu1

  • 1Ordered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|June 22, 2012
PubMed
Summary
This summary is machine-generated.

The crystal structure of a molecular salt reveals N-H⋯Br hydrogen bonds. These bonds connect cations and anions, forming a one-dimensional network in the solid state.

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Supramolecular chemistry

Background:

  • Molecular salts are compounds formed by the association of oppositely charged ions.
  • Hydrogen bonds play a crucial role in the self-assembly of crystal structures.
  • Understanding crystal packing is essential for predicting material properties.

Purpose of the Study:

  • To elucidate the crystal structure of the molecular salt C(6)H(14)N(+)·Br(-).
  • To identify the intermolecular interactions governing the crystal packing.
  • To characterize the network formed by these interactions.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
  • Crystal structure analysis was performed to identify hydrogen bonding patterns and network formation.

Main Results:

  • The crystal structure of the molecular salt C(6)H(14)N(+)·Br(-) was successfully determined.
  • N-H⋯Br hydrogen bonds were identified as the primary intermolecular forces.
  • These hydrogen bonds link the cations (C(6)H(14)N(+)) and anions (Br(-)) into a one-dimensional network.

Conclusions:

  • The crystal structure is characterized by a 1D network formed through N-H⋯Br hydrogen bonds.
  • This supramolecular arrangement highlights the importance of hydrogen bonding in molecular salt crystal engineering.
  • The findings contribute to the understanding of structure-property relationships in ionic organic materials.