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Updated: Jun 1, 2026
14:11
Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
N-Phenyl-pyrrolidine-1-carbothio-amide
1Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China.
Summary
Researchers synthesized a novel compound, C(11)H(14)N(2)S, using 1-isothiocyanato-benzene and pyrrolidine. Crystal analysis revealed significant intermolecular N-H⋯S interactions, offering insights into molecular assembly.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- The synthesis of novel organic compounds is crucial for advancing materials science and drug discovery.
- Understanding intermolecular interactions is key to predicting and controlling crystal packing and material properties.
Purpose of the Study:
- To synthesize and characterize a new organic compound with the molecular formula C(11)H(14)N(2)S.
- To investigate the crystal structure of the synthesized compound and identify any significant intermolecular interactions.
Main Methods:
- Synthesis via the reaction of 1-isothiocyanato-benzene with pyrrolidine.
- Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
Main Results:
- Successful synthesis of the target compound C(11)H(14)N(2)S.
- The crystal structure revealed the presence of intermolecular hydrogen bonds of the N-H⋯S type.
- Detailed structural analysis confirmed the molecular geometry and packing arrangement.
Conclusions:
- The reaction between 1-isothiocyanato-benzene and pyrrolidine yields a novel compound with potential applications in organic synthesis.
- The identified N-H⋯S interactions play a significant role in stabilizing the crystal lattice and directing molecular assembly.
- This study contributes to the understanding of structure-property relationships in organic sulfur-nitrogen compounds.
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01:11Aryldiazonium 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 para position.
01:19Diazonium 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.
01:25Basicity of Heterocyclic Aromatic Amines
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).
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
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, or cyano...
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01:371° 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.
01:261° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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