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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).
6.2K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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...
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Insensitive Nuclei Enhanced by Polarization Transfer (INEPT)01:15

Insensitive Nuclei Enhanced by Polarization Transfer (INEPT)

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Insensitive Nuclei Enhanced by Polarization Transfer (INEPT) is an advanced Nuclear Magnetic Resonance (NMR) technique specifically designed to detect and enhance the signals of low-abundance nuclei, such as carbon-13 and nitrogen-15, in small molecules. The fundamental principle behind INEPT is the transfer of polarization from a more abundant and highly polarizable nucleus, typically hydrogen-1, to the low-abundance nucleus of interest. This process effectively boosts the NMR signal of the...
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¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

1.1K
When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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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,...
4.1K
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.
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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[1,4]Ditellurino[2,3-b:5,6-b']di-pyrazine.

Donna Franklin1, Aundrea Lee1, Frank R Fronczek2

  • 1Department of Chemistry, Lafayette, LA 70403, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

The first heavy chalcogen-containing [1,4]ditellurino[2,3-b:5,6-b]dipyrazine exhibits a folded structure due to larger tellurium atoms. Intermolecular interactions form spiral supramolecular assemblies.

Keywords:
crystal structureheterocyclicpyrazinesupra­moleculartellurium

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Area of Science:

  • Materials Science
  • Crystallography
  • Inorganic Chemistry

Background:

  • Heterocyclic compounds containing chalcogens are crucial in materials science.
  • Previous studies focused on lighter chalcogen analogs, leaving heavy chalcogen systems underexplored.

Purpose of the Study:

  • To synthesize and characterize the first [1,4]ditellurino[2,3-b:5,6-b]dipyrazine, incorporating heavy chalcogens.
  • To investigate the structural and intermolecular properties of this novel compound.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, dihedral angles, and intermolecular contacts.

Main Results:

  • The compound C8H4N4Te2, [1,4]ditellurino[2,3-b:5,6-b]dipyrazine, was successfully synthesized and characterized.
  • Unlike its planar sulfur analog, this molecule is folded along the Te⋯Te axis with a dihedral angle of 57.9°.
  • Intermolecular Te⋯N contacts (2.894–2.963 Å) lead to the formation of spiral supramolecular assemblies and helical columns.

Conclusions:

  • The incorporation of heavy chalcogens (tellurium) significantly influences the molecular geometry, leading to a non-planar structure.
  • The observed intermolecular Te⋯N interactions are key to the formation of extended supramolecular architectures.
  • This study expands the scope of [1,4]chalcogenadipyrazines and highlights the role of heavy chalcogens in crystal engineering.