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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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 tetrahedral value,...
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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 was based on the...
Cycloalkanes02:28

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

1,2-BN cyclohexane: synthesis, structure, dynamics, and reactivity.

Wei Luo1, Lev N Zakharov, Shih-Yuan Liu

  • 1Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.

Journal of the American Chemical Society
|July 27, 2011
PubMed
Summary
This summary is machine-generated.

Researchers synthesized the first 1,2-boron nitride (BN) cyclohexane, a BN/CC isostere. This stable compound releases dihydrogen upon heating and exhibits a lower ring inversion barrier than cyclohexane.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Area of Science:

  • * Inorganic Chemistry
  • * Organic Chemistry
  • * Materials Science

Background:

  • * Boron-nitrogen (BN) isosterism offers a route to novel carbon-based compound structures.
  • * Cyclohexane is a fundamental carbocyclic scaffold with well-studied conformational properties.

Purpose of the Study:

  • * To report the first synthesis and characterization of 1,2-BN cyclohexane, the BN isostere of cyclohexane.
  • * To investigate the thermal stability and reactivity of 1,2-BN cyclohexane.
  • * To compare the ring inversion dynamics of 1,2-BN cyclohexane with cyclohexane.

Main Methods:

  • * Synthesis of 1,2-BN cyclohexane via novel chemical routes.
  • * Spectroscopic characterization (e.g., NMR, IR) and elemental analysis.
  • * Computational studies and experimental analysis of conformational dynamics.

Main Results:

  • * Successful synthesis and full characterization of the parent 1,2-BN cyclohexane.
  • * 1,2-BN cyclohexane is air- and water-stable.
  • * Thermal activation leads to trimer formation with dihydrogen release.
  • * Lower activation barrier for ring inversion compared to cyclohexane observed.

Conclusions:

  • * BN/CC isosterism is a powerful strategy for generating structurally diverse compounds.
  • * 1,2-BN cyclohexane represents a new class of stable heterocyclic compounds.
  • * The electronic and structural modifications induced by BN/CC isosterism impact molecular dynamics.