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Updated: Jun 1, 2026
05:07
Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
Published on: June 23, 2019
3-(3,5-Dimethyl-1H-pyrazol-1-yl)propanamide.
Jian-Feng Zhang1, Feng Huang, Shu-Jiao Chen
1State Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China.
Summary
This study reveals that C(8)H(13)N(3)O molecules form a stable three-dimensional crystal network. This network is primarily stabilized by intermolecular hydrogen bonds, including N-H⋯N and N-H⋯O interactions.
Area of Science:
- Crystal engineering
- Supramolecular chemistry
- Materials science
Background:
- Understanding intermolecular forces is crucial for designing novel materials.
- Hydrogen bonding plays a significant role in crystal lattice formation and stability.
- The specific compound C(8)H(13)N(3)O was investigated for its potential in crystal engineering.
Purpose of the Study:
- To elucidate the crystal structure of C(8)H(13)N(3)O.
- To identify and analyze the intermolecular interactions responsible for crystal stabilization.
- To explore the potential of this compound in forming extended supramolecular architectures.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks, including N-H⋯N, N-H⋯O, and C-H⋯O interactions.
- Computational methods may be used to further analyze interaction energies (if applicable, though not explicitly stated in the abstract).
Main Results:
- The crystal structure of C(8)H(13)N(3)O was successfully determined.
- Molecules are interconnected via a robust three-dimensional network facilitated by strong intermolecular N-H⋯N and N-H⋯O hydrogen bonds.
- Weak intermolecular C-H⋯O hydrogen bonds contribute to the overall crystal lattice stabilization.
Conclusions:
- The compound C(8)H(13)N(3)O exhibits a well-defined three-dimensional supramolecular structure.
- Intermolecular hydrogen bonding is the dominant driving force for the observed crystal packing.
- The findings provide insights into the rational design of crystalline materials with specific network topologies.
Related Concept Videos
01:28Preparation of 1° Amines: Gabriel Synthesis
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
01:17Nomenclature of Primary Amines
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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.
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.