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Diazonium Group Substitution: –OH and –H

Diazonium 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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

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...

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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...

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

Electrophilic Addition to Alkynes: Hydrohalogenation

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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

Gui-Ming Deng, Zhen Chen, Chao-Run Wang

Acta Crystallographica. Section E, Structure Reports Online

|January 20, 2012

Summary

This summary is machine-generated.

This study details the molecular structure of C(16)H(14)N(2)O, revealing a 23.5° dihedral angle between its phenyl rings. The crystal structure shows molecules linked by N-H-O hydrogen bonds, forming chains along the a axis.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Crystal engineering utilizes intermolecular forces, such as hydrogen bonds, to design materials with specific structures and functions.

Purpose of the Study:

To elucidate the crystal structure and molecular geometry of the title compound, C(16)H(14)N(2)O.
To investigate the intermolecular interactions governing the solid-state packing of this molecule.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and bond parameters.
Analysis of the crystal structure identified the presence and geometry of hydrogen bonding interactions.

Main Results:

The molecular structure of C(16)H(14)N(2)O was determined, with a significant dihedral angle of 23.5(6)° between the two phenyl rings.
A detailed analysis of the crystal packing revealed the formation of extended chains through N-H-O hydrogen bonds, oriented along the crystallographic a axis.

Conclusions:

The determined dihedral angle provides insight into the conformational preferences of the molecule in the solid state.
The observed hydrogen bonding network highlights the role of intermolecular forces in dictating crystal architecture and suggests potential for further crystal engineering applications.