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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
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Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Proton-assisted hydrogen activation on polyhedral cations.

Beatriz Calvo1, Ramón Macías, Maria Jose Artigas

  • 1Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea-ISQCH, Universidad de Zaragoza-CSIC, C/Pedro Cerbuna 12, 50009 Zaragoza, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 13, 2013
PubMed
Summary

Protonation of rhodathiaboranes with triflic acid yields stable cationic species. These compounds exhibit unique conformational isomerism and facilitate proton-assisted hydrogen activation, showcasing novel reactivity in boron-containing materials.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

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

Published on: February 15, 2016

Area of Science:

  • Organometallic Chemistry
  • Boron Chemistry
  • Coordination Chemistry

Background:

  • Rhodathiaboranes are a class of organometallic compounds containing rhodium, sulfur, and boron.
  • Understanding the reactivity and structural properties of these polyhedral clusters is crucial for developing new catalytic systems.
  • Protonation is a common method to modify the electronic and structural properties of metal-boron clusters.

Purpose of the Study:

  • To investigate the reaction of specific rhodathiaborane complexes with triflic acid.
  • To characterize the resulting protonated species and their structural features.
  • To explore the reactivity of these new cationic rhodathiaboranes, particularly in hydrogen activation.

Main Methods:

  • Treatment of 1,1-(PR3)2-3-(Py)-closo-1,2-RhSB9H8 complexes with triflic acid (TfOH).
  • Characterization of products using multinuclear NMR spectroscopy.
  • Single-crystal X-ray diffraction analysis for structural determination of key compounds.

Main Results:

  • Protonation occurred at the Rh(1)-B(3) edge, forming stable cationic 11-vertex closo-rhodathiaboranes.
  • Unusual conformational isomerism was observed in the solid state for one of the protonated complexes.
  • A bis-PPh3-ligated analogue underwent PPh3 ligand release and subsequent reaction with H2, demonstrating proton-assisted hydrogen activation.

Conclusions:

  • Cationic rhodathiaboranes can be synthesized and are stable under various conditions.
  • These compounds display interesting structural phenomena like conformational isomerism.
  • The study presents a new pathway for proton-assisted hydrogen activation mediated by polyhedral boron-containing compounds.