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Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

7.3K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
7.3K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.2K
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...
6.2K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.2K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.3K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.3K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.5K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.5K

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Aromatic 1,2-Azaborinin-1-yls as Electron-Withdrawing Anionic Nitrogen Ligands for Main Group Elements.

Felix Lindl1,2, Anna Lamprecht1,2, Merle Arrowsmith1,2

  • 1Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 22, 2022
PubMed
Summary

New 1,2-azaborinines were synthesized and functionalized, revealing insights into their electronic properties and structural behavior. These findings advance the understanding of organoboron chemistry and ligand design.

Keywords:
1,2-azaborinineN-functionalizationaromaticitycrystallographic analysessalt metathesis

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry
  • Materials Science

Background:

  • 1,2-Azaborinines are heterocyclic compounds with potential applications in catalysis and materials science.
  • Understanding their synthesis and reactivity is crucial for developing novel organoboron compounds.

Purpose of the Study:

  • To synthesize novel 2-aryl-3,4,5,6-tetraphenyl-1,2-azaborinines.
  • To explore the reactivity and coordination chemistry of these azaborinines.
  • To investigate the electronic and structural properties of the 1,2-azaborinin-2-yl ligand.

Main Methods:

  • Synthesis of 1,2-azaborinines via ring-expansion of borole precursors.
  • Desilylative hydrolysis and deprotonation to form group 1 salts.
  • Salt metathesis reactions with various electrophiles to form metal complexes.
  • Spectroscopic (11B NMR) and crystallographic analyses.

Main Results:

  • Successful synthesis of 2-aryl-3,4,5,6-tetraphenyl-1,2-azaborinines with silicon and tin substituents.
  • Formation of group 1 salts (Li, Na, K) with distinct aggregation behaviors.
  • Synthesis of group 2, 13, and 15 1,2-azaborinin-2-yl complexes via salt metathesis.
  • 1,2-azaborinin-2-yl ligand exhibits electron-withdrawing properties, comparable to bromide.
  • Correlation between ring twisting, N-substituent tilt angle, and 11B NMR chemical shifts.

Conclusions:

  • The study presents a versatile synthetic route to functionalized 1,2-azaborinines.
  • The electronic and structural properties of the 1,2-azaborinin-2-yl ligand can be tuned by substituents.
  • These findings contribute to the development of novel organoboron compounds with tailored properties.