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Hybridization of Atomic Orbitals I

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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...

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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.

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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.

Regioselectivity and Stereochemistry of Hydroboration

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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.

Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

Carbene-stabilized beryllium borohydride.

Robert J Gilliard¹, Mariham Y Abraham, Yuzhong Wang

¹Department of Chemistry and the Center for Computational Chemistry, The University of Georgia, Athens, Georgia 30602-2556, USA.

Journal of the American Chemical Society

|June 8, 2012

Summary

This summary is machine-generated.

Researchers synthesized novel N-heterocyclic carbene-stabilized beryllium compounds. These compounds undergo unique dual reduction reactions, offering new pathways in organometallic chemistry and material science.

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Published on: November 30, 2022

Area of Science:

Organometallic Chemistry
Inorganic Chemistry
Catalysis

Background:

N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
Beryllium compounds exhibit unique reactivity due to their electronic properties.

Purpose of the Study:

To synthesize and characterize novel NHC-stabilized beryllium complexes.
To investigate the reactivity of these complexes, particularly in reduction reactions.

Main Methods:

Reaction of N-heterocyclic carbene (L:) with beryllium dichloride (BeCl2) to form L:BeCl2 (1).
Preparation of carbene-stabilized beryllium borohydride monomer L:Be(BH4)2 (2) using LiBH4.
Synthesis of compound 3 via reaction of 2 with Na2[Fe(CO)4]·dioxane.

Main Results:

Quantitative yield of L:BeCl2 (1).
Successful preparation of the carbene-stabilized beryllium borohydride monomer (2).
Observation of an unusual "dual reduction" of the imidazole ring in compound 3, involving hydroboration and hydrogenation.

Conclusions:

Novel NHC-stabilized beryllium complexes were synthesized.
A unique dual reduction pathway was observed in an imidazole-based beryllium compound.
These findings expand the scope of beryllium chemistry and reductive transformations.