N'-[(5-Methyl-furan-2-yl)methyl-ene]isonicotinohydrazide
1Microscale Science Institute, Weifang University, Weifang 261061, People's Republic of China.
Summary
Researchers synthesized a novel compound C(12)H(11)N(3)O(2) from isonicotinohydrazide and 5-methyl-furan-2-carbaldehyde. Crystal analysis revealed specific ring interactions and intermolecular forces stabilizing its structure.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Isonicotinohydrazide is a versatile precursor in organic synthesis.
- Furan derivatives are important heterocyclic compounds with diverse applications.
- Understanding molecular interactions is key to designing new materials.
Purpose of the Study:
- To synthesize and characterize a new chemical entity derived from isonicotinohydrazide and a furan derivative.
- To elucidate the three-dimensional structure and crystal packing of the synthesized compound.
- To investigate the nature of intermolecular interactions governing crystal formation.
Main Methods:
- Chemical synthesis involving the reaction of isonicotinohydrazide and 5-methyl-furan-2-carbaldehyde.
- Single-crystal X-ray diffraction to determine molecular and crystal structure.
- Analysis of bond angles, dihedral angles, and intermolecular interactions.
Main Results:
- The title compound, C(12)H(11)N(3)O(2), was successfully synthesized.
- X-ray crystallography revealed a dihedral angle of 46.90(9)° between the pyridine and furan rings.
- The crystal structure is stabilized by a bifurcated intermolecular N-H⋯(N,O) interaction.
Conclusions:
- The synthesis yielded a novel compound with potential applications in medicinal chemistry or materials science.
- The observed dihedral angle provides insight into the conformational preferences of the molecule.
- The bifurcated intermolecular interaction highlights a specific mode of crystal stabilization relevant to supramolecular chemistry.
Related Concept Videos
Nomenclature 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.
Nitrosation of Enols
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Preparation of Nitriles
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.


