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Isomerism in Alkenes02:01

Isomerism in Alkenes

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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K
UV–Vis Spectroscopy: Molecular Electronic Transitions01:16

UV–Vis Spectroscopy: Molecular Electronic Transitions

2.6K
In Ultraviolet–Visible (UV–Vis) spectroscopy, the absorption of electromagnetic radiation is used to probe the electronic structure of molecules. This technique provides insights into molecular electronic transitions, particularly the movement of electrons between different molecular orbitals. Radiation is absorbed if the energy of the electromagnetic radiation passing through the molecule is precisely equal to the energy difference between the excited and ground states. During this...
2.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.3K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.3K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.8K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
10.8K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.2K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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High-Contrast and Fast Photorheological Switching of a Twist-Bend Nematic Liquid Crystal
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Normal to abnormal ItBu·AlH3 isomerization in solution and in the solid state.

Anna M Chernysheva1, Michael Weinhart, Manfred Scheer

  • 1Institute of Chemistry, St. Petersburg State University, Universitetskaya nab. 7/9, 199034, St. Petersburg, Russia. a.y.timoshkin@spbu.ru.

Dalton Transactions (Cambridge, England : 2003)
|March 4, 2020
PubMed
Summary

An N-heterocyclic carbene aluminum hydride complex isomerizes to an abnormal carbene complex in polar solvents and the solid state. This isomerization is promoted by solvent polarity, as confirmed by structural and computational studies.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Area of Science:

  • Organometallic Chemistry
  • Carbene Chemistry
  • Solid-State Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Aluminum hydride complexes offer unique reactivity profiles.
  • Isomerization reactions are crucial for understanding reaction mechanisms and developing new synthetic routes.

Purpose of the Study:

  • To investigate the isomerization of an N-heterocyclic carbene (NHC) aluminum hydride complex.
  • To characterize the resulting abnormal carbene complex.
  • To elucidate the role of solvent polarity and solid-state effects on the isomerization process.

Main Methods:

  • Synthesis and characterization of NHC-aluminum hydride complexes.
  • Single crystal X-ray diffraction for structural determination.
  • Nuclear Magnetic Resonance (NMR) spectroscopy and Density Functional Theory (DFT) computations.

Main Results:

  • Observation of the isomerization of ItBu·AlH3 to aItBu·AlH3 in polar solvents and the solid state.
  • Structural characterization of both the normal and abnormal carbene complexes.
  • DFT calculations and NMR studies confirmed the promotion of isomerization by solvent polarity.

Conclusions:

  • The isomerization of NHC-aluminum hydride complexes is feasible in polar media and the solid state.
  • Solvent polarity plays a significant role in facilitating this isomerization.
  • DFT studies provide insights into the potential reaction pathways for the observed isomerization.