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Related Concept Videos

Structure of Amines01:19

Structure of Amines

3.1K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
3.1K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.0K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
3.0K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.5K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.5K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
15.0K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

13.9K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
13.9K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

17.7K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
17.7K

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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U-Shaped Helical Azaarenes: Synthesis, Structures, and Properties.

Kexiang Zhao1, Guankui Long2, Wenbo Liu1

  • 1School of Materials Science and Engineering , Nanyang Technological University , Singapore 639798 , Singapore.

The Journal of Organic Chemistry
|December 5, 2019
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Summary

Researchers synthesized U-shaped helical azaarenes, confirming their unique helical structures through crystal analysis. This study advances the understanding of complex molecular architectures.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Azaarenes are nitrogen-containing aromatic compounds with diverse applications.
  • Helical structures in organic molecules can lead to unique chiroptical and material properties.
  • Designing and synthesizing complex helical architectures remains a challenge in organic chemistry.

Purpose of the Study:

  • To synthesize and characterize a novel series of U-shaped helical azaarenes.
  • To investigate the structural and physical properties of these helical compounds.
  • To confirm the presence and nature of helicity in the solid state.

Main Methods:

  • Multi-step organic synthesis to construct the U-shaped azaarene framework.
  • Single-crystal X-ray diffraction to determine solid-state molecular structures.
  • Spectroscopic techniques (e.g., NMR, UV-Vis) to analyze compound properties.

Main Results:

  • Successful synthesis of a series of U-shaped helical azaarenes was achieved.
  • Crystal structures unequivocally confirmed the U-shaped helical conformation.
  • The obtained solid-state structures provide direct evidence of molecular helicity.

Conclusions:

  • The study demonstrates a viable synthetic route to U-shaped helical azaarenes.
  • The confirmed helicity in the solid state opens possibilities for their use in chiral materials.
  • This work contributes to the field of helical organic molecules and their structural diversity.