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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.

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...

Rate-Determining Steps

Rate-Determining Steps

Relating Reaction Mechanisms
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...

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...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

Radical Reactivity: Nucleophilic Radicals

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...

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Updated: May 29, 2025

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

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Published on: December 6, 2021

Predicting Dinitrogen Activation by Boron Radical Cations.

Chenshu Dai¹, Yongbing Gu¹, Shengrong Guo¹

¹Department of Ecology, Lishui University, Lishui, 323000, China.

Inorganic Chemistry

|February 3, 2025

Summary

Boron radical cations efficiently activate dinitrogen (N₂) under mild conditions. This metal-free approach utilizes σ-donation and π-backdonation, offering a promising alternative for nitrogen fixation.

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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

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Published on: January 6, 2016

Area of Science:

Inorganic Chemistry
Computational Chemistry
Materials Science

Background:

Dinitrogen (N₂) activation is challenging due to its strong triple bond.
Main group elements offer a promising, yet rare, alternative to transition metals for N₂ activation.

Purpose of the Study:

To investigate the feasibility of N₂ activation by boron radical cations.
To elucidate the mechanism of N₂ activation by boron radical cations using computational methods.

Main Methods:

Comprehensive density functional theory (DFT) calculations.
Principal Interacting Spin Orbitals (PISOs) analysis.
Intrinsic Bond Orbitals (IBOs) analysis.

Main Results:

N₂ activation by boron radical cations is kinetically and thermodynamically favorable (ΔG = -36.8 kcal/mol, barrier = 7.3 kcal/mol).
Activation proceeds via two perpendicular interactions: σ-donation and π-backdonation.
π-backdonation is identified as crucial for the N₂ activation process.

Conclusions:

Boron radical cations provide an effective metal-free pathway for N₂ activation under mild conditions.
This study highlights the potential of boron chemistry in developing new strategies for nitrogen fixation.