Related Experiment Video

Updated: May 14, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Synthesis, crystal structure, Hirshfeld surface analysis and experimental and theoretical study of new azo compound

Souheyla Chetioui¹, Nawel Khelloul², Nourdine Boukabcha³

¹VEHDD Laboratory, University of M'sila, 28000 M'sila, Algeria.

Acta Crystallographica. Section C, Structural Chemistry

|May 13, 2025

Abstract:

The azo dye methyl 2-{2-[(E)-2-oxo-1,2-dihydronaphthalen-1-ylidene]hydrazin-1-yl}benzoate, C₁₈H₁₄N₂O₃, was synthesized and subjected to an extensive experimental and theoretical study. Crystallizing in the monoclinic space group P2₁/c, the compound was analyzed using X-ray diffraction and density functional theory (DFT) calculations with the B3LYP functional and 6-311G(d,p) basis set. The results demonstrated a strong correlation between the experimental and theoretical geometrical parameters, with one of the tautomeric forms (denoted K, the NH/C=O tautomer) showing greater stability. Hirshfeld surface analysis revealed significant H...H, C...H and O...H interactions. Energy framework analysis indicated that dispersion forces play a crucial role in crystal stability. The vibrational and UV spectra were consistent between the experimental and theoretical data. The small energy gap in the K tautomeric form suggests higher polarizability, making it a promising candidate for optically active materials. Chemical reactivity descriptors highlighted the enhanced reactivity of the K tautomer. Reduced density gradient (RDG) analysis showed stronger hydrogen bonding in the second tautomer (denoted E, the N=N/C-OH tautomer), while molecular electrostatic potential (MEP) analysis identified high electron density around the O atoms, suggesting electrophilic sites. The high first-order hyperpolarizability of the compound points to potential nonlinear optical (NLO) applications. Biological studies suggested potential antipyretic activity, with COX-2 identified as a promising target for inhibition due to its strong binding affinity and effectiveness. These findings support further investigation into COX-2 inhibition.

Keywords:

DFT Hirshfeld surface MEP NLO RDG X-ray diffraction antipyretic azo compound crystal structure molecular electrostatic potential nonlinear optical reduced density gradient

More Related Videos

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

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.

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

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

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...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

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,...

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

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...

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

Articles linked to this work by shared authors, journal, and citation graph.

A thiosemicarbazone derivative as a potential multi-target inhibitor: Molecular docking, DFT, QTAIM, and NLO investigation of thione and thiol tautomers.

Talanta·2026

Juniperus phoenicea L. Essential Oil from Ain El Orak (Algeria): Chemical Analysis by GC/MS, In Vitro Antioxidant and In Vivo/In Silico Gastroprotective and Hepatoprotective Effects.

Foods (Basel, Switzerland)·2026

Structural, nonlinear optical, and molecular docking studies of schiff base compounds as multi-target inhibitors of AChE, BChE, and carbonic anhydrases.

Scientific reports·2025

Synthesis, characterization, DFT investigation and in silico anti-eczema evaluation of a novel thiazolidinone derivative.

Acta chimica Slovenica·2025

Exploring Pyrimidine-Based azo Dyes: Vibrational spectroscopic Assignments, TD-DFT Investigation, chemical Reactivity, HOMO-LUMO, ELF, LOL and NCI-RDG analysis.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2024

Conformation and vibrational spectroscopic analysis of 2,6-bis(4-fluorophenyl)-3,3-dimethylpiperidin-4-one (BFDP) by DFT method: A potent anti-Parkinson's, anti-lung cancer, and anti-human infectious agent.

Heliyon·2023

See all related articles