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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.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic 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.

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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.

Amides to Carboxylic Acids: Hydrolysis

Amides to Carboxylic Acids: Hydrolysis

Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...

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Related Experiment Video

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

N'-(3-Methoxy-benzyl-idene)aceto-hydrazide.

Lu-Ping Lv, Tie-Ming Yu, Wen-Bo Yu

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a C(10)H(12)N(2)O(2) molecule, revealing a planar acetohydrazide group and trans configuration. Molecules form dimers via hydrogen bonds, creating ribbon-like crystal structures.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
The acetohydrazide moiety is a common functional group in various biologically active compounds.
Benzene rings and methoxy groups influence molecular packing and properties.

Purpose of the Study:

To elucidate the detailed crystal structure and molecular geometry of the title compound C(10)H(12)N(2)O(2).
To investigate the intermolecular interactions, including hydrogen bonding and C-H interactions, governing crystal packing.
To characterize the planarity and dihedral angles within the molecule and their impact on overall structure.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
Geometric parameters such as bond lengths, bond angles, and dihedral angles were precisely measured.
Intermolecular interactions were identified and analyzed using hydrogen bond and weak interaction analysis.

Main Results:

The acetohydrazide group was found to be planar (within 0.012(1) Å) and formed a dihedral angle of 5.25(8)° with the benzene ring.
The methoxy group exhibited coplanarity with the benzene ring (C-O-C-C = 0.1(2)°).
The molecule adopts a trans configuration around the C=N double bond, with crystal packing dominated by N-H⋯O hydrogen bonds forming dimers and C-H⋯O hydrogen bonds forming ribbon-like structures, alongside C-H⋯π interactions.

Conclusions:

The study provides precise structural data for C(10)H(12)N(2)O(2), highlighting the interplay of planarity and dihedral angles.
Intermolecular hydrogen bonding and C-H⋯π interactions are key factors in the observed crystal architecture.
The findings contribute to the understanding of molecular assembly in organic crystals.