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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.7K
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.
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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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).
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.2K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.3K
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,...
2.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.1K
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...
2.1K

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The Pyrazinacenes.

Gary J Richards1, Jonathan P Hill2

  • 1Department of Applied Chemistry, Graduate School of Engineering and Science, Shibaura Institute of Technology, Fukasaku 307, Minuma-ku, Saitama-shi, Saitama 337-8570, Japan.

Accounts of Chemical Research
|July 29, 2021
PubMed
Summary
This summary is machine-generated.

Pyrazinacenes, nitrogen-rich molecules, offer unique electronic and protonic transport properties distinct from hydrocarbon acenes. Their tunable synthesis and diverse functionalities show promise for advanced applications in electronics and bioimaging.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Pyrazinacenes are nitrogen-containing heteroacenes structurally analogous to hydrocarbon acenes.
  • The incorporation of multiple nitrogen atoms imparts unique electronic and chemical properties compared to their carbon-only counterparts.
  • These properties include enhanced stability of reduced states and tunable redox behavior.

Purpose of the Study:

  • To synthesize and characterize extended pyrazinacenes, from hexaazaanthracene (N6) to tetradecaazaheptacene (N14).
  • To investigate the emergent properties arising from the high nitrogen content and extended pi-conjugation.
  • To explore potential applications in organic electronics, catalysis, and bioimaging.

Main Methods:

  • Synthesis of extended pyrazinacene derivatives.
  • X-ray crystallographic studies for structural elucidation.
  • Spectroscopic and electrochemical methods to probe electronic and protonic properties.
  • Scanning tunneling microscopy (STM) for on-surface studies.

Main Results:

  • Extended pyrazinacenes exhibit unusual linear tautomeric processes due to proton delocalization.
  • Decazapentacene (N10) displays multistability in oxidation states, suggesting redox catalytic potential.
  • The longest pyrazinacene (N14) shows amphiprotism coupled with near-infrared fluorescence, indicating pH-dependent behavior.
  • On-surface oxidation-state switching was observed via STM.

Conclusions:

  • Pyrazinacenes represent a versatile class of nitrogenous heteroacenes with unique protonic and electronic transport capabilities.
  • Their tunable synthesis allows for tailored molecular design for specific applications.
  • Emerging properties like proton delocalization, redox multistability, and pH-coupled fluorescence highlight their potential in molecular electronics, catalysis, and bioimaging.