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Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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N'-[(E)-3-Pyridylmethyl-idene]benzo-hydrazide.

Liyuan Wen¹, Handong Yin, Wenkuan Li

¹College of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

Researchers synthesized a novel compound, C(13)H(11)N(3)O, using benzohydrazide and nicotinaldehyde. Its crystal structure reveals a 47.78° dihedral angle and stabilization via intermolecular hydrogen bonds.

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Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Benzohydrazide and nicotinaldehyde are common organic precursors.
Understanding molecular interactions is key in crystal engineering.

Purpose of the Study:

To synthesize and characterize a novel organic compound.
To investigate the structural and bonding properties of the synthesized molecule.

Main Methods:

Chemical synthesis involving the reaction of benzohydrazide and nicotinaldehyde.
X-ray diffraction analysis to determine the crystal structure.

Main Results:

Successful synthesis of the title compound, C(13)H(11)N(3)O.
Determination of a 47.78° dihedral angle between the aromatic rings.
Identification of intermolecular N-H⋯N hydrogen bonds stabilizing the crystal structure.

Conclusions:

The synthesized compound exhibits a specific non-planar conformation.
Intermolecular hydrogen bonding plays a crucial role in the crystal packing and stability.