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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

14.9K
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...
14.9K
Nucleophilic Substitution Reactions02:34

Nucleophilic Substitution Reactions

19.2K
Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
19.2K
¹H NMR of Labile Protons: Deuterium (²H) Substitution00:48

¹H NMR of Labile Protons: Deuterium (²H) Substitution

1.3K
This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.
1.3K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.7K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.7K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

13.8K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
13.8K

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Transformation of Organic Household Leftovers into a Peat Substitute
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An H-Substituted Rhodium Silylene.

Connor S MacNeil1, Paul G Hayes1

  • 1Canadian Centre for Research in Advanced Fluorine Technologies (C-CRAFT), Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive W, Lethbridge, T1K 3M4, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 27, 2019
PubMed
Summary

This study details the synthesis of neutral rhodium silylenes from rhodium(I) complexes and hydrosilanes. These novel silylene complexes exhibit short Rh-Si bonds and altered ligand coordination, confirmed by spectroscopy and crystallography.

Keywords:
H-substituted silylenehydrosilation catalysismetal-ligand cooperativitypincer ligandsrhodium

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Area of Science:

  • Organometallic Chemistry
  • Rhodium Complexes
  • Silylene Chemistry

Background:

  • Organometallic rhodium(I) complexes display diverse reactivity.
  • Silylenes are silicon analogues of carbenes, with unique bonding properties.
  • Understanding silylene formation and characterization is crucial for catalysis and materials science.

Purpose of the Study:

  • To investigate the reactivity of rhodium(I) complexes with hydrosilanes.
  • To isolate and characterize novel neutral rhodium silylene complexes.
  • To elucidate the structural and electronic properties of the resulting silylenes.

Main Methods:

  • Addition reactions of hydrosilanes (PhRSiH2) to rhodium(I) complexes ((iPrNNN)Rh(COE) and (iPrNNN)Rh(CO)).
  • Isolation and characterization of rhodium(III) silyl hydride and rhodium(I) silylene complexes.
  • Multinuclear NMR spectroscopy, X-ray crystallography, and Density Functional Theory (DFT) computations.

Main Results:

  • Isolation of neutral rhodium(I) silylenes (iPrNNN)(CO)Rh=SiRPh (R=H, Ph).
  • Characterization of short Rh-Si bonds (2.262(1) Å and 2.2702(7) Å) in the silylene complexes.
  • Observation of a change in the (iPrNNN) ligand bonding mode and loss of H2 during the reaction.

Conclusions:

  • Divergent reactivity of rhodium(I) complexes with hydrosilanes leads to neutral silylenes.
  • The isolated rhodium silylenes possess well-defined structures with short Rh-Si bonds.
  • Deuterium labeling confirmed the loss of H2, providing insights into the reaction mechanism.