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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.1K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.1K
Relative Reactivity of Carboxylic Acid Derivatives01:13

Relative Reactivity of Carboxylic Acid Derivatives

4.0K
Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
4.0K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.7K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.7K
Preparation of Amides01:29

Preparation of Amides

4.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.2K
Preparation of 1&deg; Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.8K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.8K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.6K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.6K

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Cationic Bismuth Amides: Accessibility, Structure, and Reactivity.

Hannah Dengel1, Crispin Lichtenberg1

  • 1Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 13, 2016
PubMed
Summary
This summary is machine-generated.

This study explores new cationic bismuth amides, revealing phenyl transfer with tetraphenylborate counteranions and enhanced stability with fluorinated boron compounds. These cationic bismuth species exhibit increased reactivity, forming novel guanidinates.

Keywords:
B−C bond activationamidesbismuthcationic speciesguanidinates

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Investigating cationic bismuth compounds offers new avenues in coordination chemistry.
  • Amido ligands are synthetically versatile building blocks for metal complexes.
  • Understanding ion pairing and reactivity is crucial for designing novel bismuth materials.

Purpose of the Study:

  • To synthesize and characterize novel cationic bismuth amide compounds.
  • To explore the influence of different counteranions on bismuth complex stability and reactivity.
  • To investigate the coordination chemistry and aggregation behavior of these cationic species.

Main Methods:

  • Synthesis of cationic bismuth complexes using amido ligands.
  • Characterization via multinuclear NMR (¹H, ¹¹B, ¹³C, ¹⁵N, ¹⁹F, ³¹P), IR spectroscopy, and single-crystal X-ray diffraction.
  • Computational analysis using Density Functional Theory (DFT) calculations.

Main Results:

  • Isolation and characterization of cationic bismuth amides with phenyl transfer observed using [BPh₄]⁻.
  • Enhanced stability of cationic bismuth amides achieved with fluorinated tetraarylborate counteranions.
  • Formation of solvent-separated ion pairs and investigation of their aggregation and spectroscopic properties.
  • Compounds 4 and 5 exhibit increased reactivity towards diisopropylcarbodiimide, yielding the first cationic bismuth guanidinates.

Conclusions:

  • Cationic bismuth amides can be accessed using simple amido ligands.
  • Counteranion choice significantly impacts the stability and reactivity of cationic bismuth complexes.
  • The synthesized cationic bismuth compounds serve as precursors to novel guanidinate derivatives.