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Related Concept Videos

Solvating Effects02:12

Solvating Effects

An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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Related Experiment Video

Updated: Jun 13, 2026

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

Solvent effects on isomerization in a ruthenium sulfoxide complex.

Tod A Grusenmeyer1, Beth Anne McClure, Christopher J Ziegler

  • 1Department of Chemistry and Biochemistry, Nanoscale and Quantum Phenomena Institute, Ohio University, Athens, Ohio 45701, USA.

Inorganic Chemistry
|April 24, 2010
PubMed
Summary

This study details the isomerization kinetics of a ruthenium complex with 2,2′-bipyridine, 2,2′-biquinoline, and 2-methylsulfinylbenzoate ligands. Solvent polarity significantly influences the sulfoxide isomerization rate, impacting electrochemical properties.

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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

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Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor
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Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Published on: October 26, 2017

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Last Updated: Jun 13, 2026

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

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor
07:12

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Published on: October 26, 2017

Area of Science:

  • Inorganic Chemistry
  • Coordination Chemistry
  • Photochemistry

Background:

  • Ruthenium complexes with polypyridyl ligands are widely studied for their electrochemical and photophysical properties.
  • Sulfoxide ligands offer unique coordination modes and potential for isomerization reactions.
  • Understanding ligand isomerization is crucial for designing functional metal complexes.

Purpose of the Study:

  • To synthesize and characterize the novel ruthenium complex [Ru(bpy)(biq)(OSO)](PF6).
  • To investigate the electrochemical behavior and isomerization kinetics of the sulfoxide ligand within the complex.
  • To determine the influence of solvent polarity on the isomerization rate constants.

Main Methods:

  • Synthesis and characterization of the ruthenium complex using UV-visible and infrared spectroscopy.
  • Electrochemical studies employing cyclic voltammetry.
  • Kinetic analysis of sulfoxide isomerization in various organic solvents.

Main Results:

  • The complex [Ru(bpy)(biq)(OSO)](PF6) was successfully synthesized and characterized.
  • UV-Vis and IR data indicated intramolecular S-->O and O-->S isomerization of the sulfoxide ligand.
  • Cyclic voltammetry demonstrated isomerization triggered by redox events.
  • The rate constant for S-->O isomerization varied significantly with solvent: 3.2 s⁻¹ (propylene carbonate), 0.80 s⁻¹ (acetonitrile), and 0.26 s⁻¹ (dichloromethane).

Conclusions:

  • The study elucidates the structure-property relationships in a novel ruthenium complex.
  • Solvent-dependent isomerization kinetics of the sulfoxide ligand were quantified.
  • Redox-triggered isomerization offers potential for electrochemical control in ruthenium-based systems.