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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.2K
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
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

3.2K
When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
3.2K
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
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.7K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.7K
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

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Crystal structures and Hirshfeld surface analyses of two precursors of the etoxazole metabolite 'R8'.

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<i>catena</i>-Poly[[(5,5'-dimethyl-2,2'-bi-pyridine)nickel(II)]-μ<sub>2</sub>-azido-κ<sup>2</sup> <i>N</i>:<i>N</i>-μ<sub>2</sub>-azido-κ<sup>2</sup> <i>N</i>:<i>N</i>']: synthesis, crystal structure, Hirshfeld surface analysis and DFT calculations.

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Related Experiment Video

Updated: Aug 22, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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1-(3,5-Di-nitro-benzo-yl)-4-(2-meth-oxy-phen-yl)piper-azine.

Chayanna Harish Chinthal1, Channappa N Kavitha2, Hemmige S Yathirajan1

  • 1Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.

Iucrdata
|November 7, 2022
PubMed
Summary

The crystal structure of C18H18N4O6 reveals a chair conformation in the piperazine ring and planar amidic nitrogen. Molecules self-assemble via pi-stacking interactions into sheets, without hydrogen bonding.

Keywords:
crystalmol­ecular conformationsynthesisπ–π stacking

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular conformation and intermolecular interactions is crucial for predicting material properties.
  • Piperazine derivatives are common scaffolds in medicinal chemistry and materials science.
  • Pi-stacking interactions play a significant role in the self-assembly of organic molecules.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C18H18N4O6.
  • To investigate the conformational preferences of the piperazine ring and nitrogen atoms.
  • To identify and characterize intermolecular interactions governing crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, and conformational parameters.
  • Intermolecular interaction analysis, including pi-stacking and hydrogen bonding assessment.

Main Results:

  • The piperazine ring adopts a chair conformation.
  • The amidic nitrogen atom is planar (sum of angles = 360°), while the non-amidic nitrogen is pyramidal (343°).
  • Molecules form π-stacked sheets through two independent π(nitro-benzene)⋯π(meth-oxy-benzene) stacking interactions, with inter-centroid separations of 3.8444(12) and 3.9197(12) Å.
  • No hydrogen bonds were observed in the crystal structure.

Conclusions:

  • The crystal packing is dominated by π-stacking interactions, leading to the formation of layered structures.
  • The distinct geometries of the nitrogen atoms influence the molecule's conformation and intermolecular interactions.
  • The findings provide insights into the structure-property relationships of this class of organic compounds.