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Regioselectivity and Stereochemistry of Hydroboration

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 Alkenes

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 I

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...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Structural Isomerism

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...

Preparation of Alcohols via Addition Reactions

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...

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Multifunctionality of silver closo-boranes.

Mark Paskevicius^1,2, Bjarne R S Hansen¹, Mathias Jørgensen¹

¹Department of Chemistry and Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Langelandsgade 140, Aarhus C DK-8000, Denmark.

Nature Communications

|April 27, 2017

Summary

This summary is machine-generated.

New silver borane semiconductors exhibit high ion conductivity and form silver nano-filaments. These materials show promise for applications in photocatalysis, solid-state ionics, and nano-wire production.

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Area of Science:

Materials Science
Solid-State Chemistry
Nanotechnology

Background:

Silver compounds have diverse historical applications, including in catalysis and antimicrobial uses.
Semiconducting properties of silver compounds are of interest for advanced material applications.

Purpose of the Study:

To introduce a new class of silver borane semiconductors (Ag2B10H10 and Ag2B12H12).
To investigate their electronic, ionic, and structural properties.
To explore their potential in various technological fields.

Main Methods:

Synthesis and characterization of silver borane compounds.
Measurement of bandgap energy and ion conductivity.
Transmission electron microscopy (TEM) for observing nano-filament formation and reabsorption.

Main Results:

The silver boranes are semiconductors with a 2.3 eV bandgap, absorbing green visible light.
They exhibit exceptionally high ion conductivity, enhanced by AgI substitution (up to 3.2 mS cm-1).
Fast silver nano-filament growth and reabsorption were observed under electron excitation in TEM.

Conclusions:

Silver closo-boranes possess unique semiconducting and ionic properties.
Their dynamic-anion facilitated Ag+ migration contributes to high ion conductivity.
These materials demonstrate multifunctionality, opening possibilities for photocatalysis, solid-state ionics, and nano-wire production.