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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).
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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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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.
3.4K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

7.8K
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...
7.8K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.8K
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,...
2.8K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.9K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.1K
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...
4.1K

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Acid-responsive rhenium(I) NHC complexes: pyrazine vs. pyridine.

Pedro O Abate1,2,3,4, José Francisco Rizo1,2, Francisco José Fernández-de-Córdova2

  • 1Departamento de Química Inorgánica, Universidad de Sevilla, C/Prof. García González 1, 41012 Seville, Spain. orivada@us.es.

Dalton Transactions (Cambridge, England : 2003)
|March 2, 2026
PubMed
Summary

This study synthesized rhenium(I) tricarbonyl complexes with N-heterocyclic carbenes. Pyrazine-containing complexes showed significant electronic shifts upon acid interaction, unlike pyridine analogs.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Rhenium(I) tricarbonyl complexes are of interest for their photophysical and electrochemical properties.
  • Understanding the influence of ligand structure on metal complex properties is crucial for designing new materials.

Purpose of the Study:

  • To synthesize and characterize novel rhenium(I) tricarbonyl complexes functionalized with pyridine and pyrazine NHCs.
  • To investigate the impact of Brønsted and Lewis acids on the electronic properties of these isosteric complexes.
  • To compare the electronic behavior of pyridine- versus pyrazine-functionalized complexes.

Main Methods:

  • Synthesis of four rhenium(I) tricarbonyl complexes.
  • Full characterization including single-crystal X-ray diffraction.
  • Electrochemical and spectroelectrochemical measurements.

Main Results:

  • Molecular structures of the complexes were determined.
  • Pyridine-containing complexes showed no significant electronic changes upon acid addition.
  • Pyrazine-containing complexes exhibited notable shifts in redox potentials due to the extra nitrogen atom's interaction with acids.
  • Brønsted acids induced larger electronic perturbations than alkali salts.

Conclusions:

  • The electronic properties of rhenium(I) NHC complexes are sensitive to the ligand's heterocyclic core.
  • The presence of an additional nitrogen atom in the pyrazine ring facilitates acid interactions, leading to significant electronic perturbations.
  • This work provides insights into the design of functional organometallic materials sensitive to acidic environments.