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Related Concept Videos

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,...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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 staggered...
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...
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

A stable Schrock-type hafnium-silylene complex.

Norio Nakata1, Toshiyuki Fujita, Akira Sekiguchi

  • 1Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.

Journal of the American Chemical Society
|December 15, 2006
PubMed
Summary
This summary is machine-generated.

The synthesis of the first stable hafnium-silylene complex, featuring a hafnium-silicon double bond, was achieved through a coupling reaction. This discovery advances organometallic chemistry and the study of low-coordinate silicon species.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Silicon Chemistry

Background:

  • Silylene complexes are reactive intermediates with limited stability.
  • Hafnium complexes offer unique electronic properties for stabilizing unusual bonding arrangements.

Purpose of the Study:

  • To synthesize and characterize the first stable hafnium-silylene complex.
  • To investigate the bonding characteristics and electronic structure of hafnium-silicon multiple bonds.

Main Methods:

  • Coupling reaction between a dilithiosilane and a hafnium precursor.
  • Isolation and characterization of the product as a phosphine adduct.
  • Spectroscopic analysis (29Si NMR) and X-ray crystallography.

Main Results:

  • Successful synthesis of the stable hafnium-silylene complex (eta-C5H4Et)2(PMe3)Hf=Si(SiMetBu2)2.
  • 29Si NMR spectroscopy confirmed the silylene ligand with a downfield shift (295.4 ppm) and JSiP coupling (15.0 Hz).
  • X-ray crystallography revealed a short Si-Hf bond length (2.6515(9) A), indicative of double-bond character.

Conclusions:

  • The synthesized compound is a Schrock-type silylene complex.
  • Natural population analysis supports a negative charge on the silicon atom, consistent with a double bond.