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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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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...

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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.

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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N'-[Bis(benzyl-sulfan-yl)methyl-idene]benzohydrazide.

Shahedeh Tayamon, Thahira Begum S A Ravoof, Mohamed Ibrahim Mohamed Tahir

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Summary

This study details the crystal structure of a hydrazonodithioate compound, revealing specific molecular torsions and dihedral angles. The research highlights the formation of a three-dimensional crystal architecture through hydrogen bonding and other intermolecular interactions.

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Area of Science:

Crystallography
Chemical Physics
Supramolecular Chemistry

Background:

Understanding molecular geometry and intermolecular forces is crucial for predicting material properties.
The hydrazonodithioate scaffold presents unique structural features for investigation.

Purpose of the Study:

To elucidate the detailed crystal structure of the title hydrazonodithioate compound.
To analyze the molecular conformation, including torsion and dihedral angles.
To identify and characterize the intermolecular interactions responsible for the crystal packing.

Main Methods:

Single-crystal X-ray diffraction analysis.
Geometric analysis of molecular conformation (torsion and dihedral angles).
Identification of hydrogen bonds (N-H⋯O) and other intermolecular interactions (C-H⋯O, C-H⋯N).

Main Results:

The amide group in the hydrazonodithioate is significantly twisted out of plane (C-N-N-C torsion angle of 139.71°).
Distinct dihedral angles were observed between the pyridine and phenyl rings (52.96°, 86.46°), with phenyl rings being nearly orthogonal (76.42°).
Supramolecular chains formed by N-H⋯O hydrogen bonds along the c-axis were identified, consolidated into a 3D architecture by C-H⋯O and C-H⋯N interactions.

Conclusions:

The study provides a precise description of the molecular and crystal structure of the hydrazonodithioate.
The observed non-planar geometry and specific dihedral angles are key conformational features.
Hydrogen bonding and C-H interactions dictate the formation of a stable three-dimensional supramolecular network in the solid state.