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Related Concept Videos

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

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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...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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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.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.2K
Nuclear Overhauser Enhancement (NOE)01:06

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1.3K
Irradiation of a spin-active nucleus causes an increase or decrease in the signal intensity of neighboring nuclei that are not necessarily chemically bonded or involved in J-coupling. This phenomenon, called the nuclear Overhauser enhancement (NOE), results from through-space interactions between the nuclear spins. The NOE effect decreases with increasing internuclear distance and is generally not observed beyond 4 angstroms. In NOE, dipole-dipole interactions between neighboring spin-active...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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3.8K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.8K
Inorganic Nitrogen Assimilation01:22

Inorganic Nitrogen Assimilation

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Nitrogen is an essential element in biological systems, forming a crucial component of proteins, nucleic acids, and other cellular constituents. Many bacteria and archaea acquire nitrogen in the form of nitrate (NO₃⁻) or ammonia (NH₃), which are then assimilated into biomolecules through specific enzymatic pathways.Assimilatory Nitrate ReductionWhen nitrate enters the cell, it undergoes a two-step reduction process known as assimilatory nitrate reduction. Initially, the enzyme...
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Two Push-Pull Channels Enhance the Dinitrogen Activation by Borylene Compounds.

Huaiyu Zhang1, Rui Yuan1, Wei Wu2

  • 1Institute of Computational Quantum Chemistry, College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang, 050024, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 6, 2019
PubMed
Summary

Borylenes, such as cyclic alkyl(amino) carbene-boron (CAAC) complexes, activate nitrogen (N2) by forming bent BNNB cores. This unique bonding involves push-pull interactions, enhancing N2 activation and catalytic capacity.

Keywords:
block localized wavefunction (BLW)borondinitrogen activationpush-pull channelsvalence bond (VB)

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Area of Science:

  • Organoboron Chemistry
  • Nitrogen Fixation
  • Theoretical Chemistry

Background:

  • Borylenes, particularly cyclic alkyl(amino) carbene-boron (CAAC) complexes, have emerged as novel agents for nitrogen (N2) activation.
  • Previous studies showed borylene-CAAC complexes can bind and activate N2, forming a bent BNNB core, unlike linear N2 in transition metal complexes.

Purpose of the Study:

  • To investigate the bonding nature of terminal end-on and end-on bridging borylene-N2 complexes using valence bond (VB) theory.
  • To elucidate the mechanism behind the bent BNNB core formation and enhanced N2 activation.

Main Methods:

  • Valence bond (VB) theory was employed to analyze the electronic structure and bonding in borylene-N2 complexes.
  • Comparison of bonding mechanisms in terminal end-on and bridging borylene-N2 systems.

Main Results:

  • In terminal end-on complexes, bonding follows a σ donation and π back-donation model, similar to transition metals.
  • In end-on bridging complexes, σ donation originates from N2's π orbitals, creating perpendicular push-pull channels.
  • This push-pull interaction is responsible for the bent BNNB geometry and enhanced N2 activation.

Conclusions:

  • The push-pull interaction in bridging borylene-N2 complexes is key to their unique reactivity and geometry.
  • Substituents on boron can modulate the bent angle and push-pull strength, influencing N2 activation.
  • (CAAC)FB demonstrates improved catalytic activity for N2 activation, validating the proposed mechanism.