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Related Concept Videos

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.
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Complexometric Titration: Ligands00:43

Complexometric Titration: Ligands

Different monodentate and polydentate ligands are used as complexing agents in complexometric titration reactions. The formation of complexes by mono- and bidentate ligands involves two or more intermediate steps, limiting their use as complexing agents. In comparison, polydentate ligands can form complexes with metal ions in a single-step process, facilitating sharper end points. This means polydentate ligands, such as amino carboxylic acid derivatives, are most commonly employed in...
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.

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Related Experiment Video

Updated: May 15, 2026

Attaching Biological Probes to Silica Optical Biosensors Using Silane Coupling Agents
09:35

Attaching Biological Probes to Silica Optical Biosensors Using Silane Coupling Agents

Published on: May 1, 2012

Sugar complexation to silicone boronic acids.

Michael A Brook1, Laura Dodge, Yang Chen

  • 1Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St. W., Hamilton ON, Canada L8S 4M1. mabrook@mcmaster.ca

Chemical Communications (Cambridge, England)
|January 17, 2013
PubMed
Summary
This summary is machine-generated.

Researchers developed novel surface-active compounds by merging silicones and boronic acids. These versatile materials allow tunable properties for diverse applications by modifying their structure and attached saccharides.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Synthesis and Characterization of Supramolecular Colloids
09:26

Synthesis and Characterization of Supramolecular Colloids

Published on: April 22, 2016

Related Experiment Videos

Last Updated: May 15, 2026

Attaching Biological Probes to Silica Optical Biosensors Using Silane Coupling Agents
09:35

Attaching Biological Probes to Silica Optical Biosensors Using Silane Coupling Agents

Published on: May 1, 2012

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Synthesis and Characterization of Supramolecular Colloids
09:26

Synthesis and Characterization of Supramolecular Colloids

Published on: April 22, 2016

Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Surface Chemistry

Background:

  • Silicones are widely used polymers with tunable properties.
  • Boronic acids are known for their ability to bind saccharides.
  • Surface-active compounds are crucial in various industrial and biological applications.

Purpose of the Study:

  • To introduce a new class of surface-active compounds.
  • To explore the tunability of these compounds through structural modifications.
  • To investigate the stabilization mechanisms of the novel compounds.

Main Methods:

  • Synthesis of novel silicone-boronic acid hybrid compounds.
  • Characterization of the compounds' surface activity.
  • Tuning of hydrophobic (silicone) and hydrophilic (saccharide) components.
  • Stabilization using Tris buffer at neutral pH.

Main Results:

  • A new class of surface-active compounds was successfully synthesized.
  • The compounds exhibit tunable properties based on silicone structure and bound saccharides.
  • Tris buffer effectively stabilizes the four-coordinate boron structure and prevents silicone hydrolysis.

Conclusions:

  • The novel silicone-boronic acid compounds offer a versatile platform for creating tailored surface-active agents.
  • Tunability of both hydrophobic and hydrophilic moieties allows for precise control over material properties.
  • The stabilization strategy ensures the integrity and performance of these compounds in aqueous environments.