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ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

Nitrosation of Enols

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.

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.

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...

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Related Experiment Video

Updated: Jun 5, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

1-Oxoisoindoline-2-carboxamide.

Bushra Maliha, Ishtiaq Hussain, M Nawaz Tahir

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study reveals the crystal structure of a C(9)H(8)N(2)O(2) molecule. Hydrogen bonding and pi-pi interactions form a 2D network, detailing molecular assembly in solid-state chemistry.

Area of Science:

Crystal engineering
Supramolecular chemistry
Organic solid-state chemistry

Background:

Understanding molecular interactions is crucial for designing materials with specific properties.
Hydrogen bonding and π-π interactions are key non-covalent forces governing crystal packing.

Purpose of the Study:

To elucidate the crystal structure of the title molecule C(9)H(8)N(2)O(2).
To investigate the role of intermolecular interactions in stabilizing the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction analysis.
Analysis of hydrogen bonding networks (N-H⋯O, C-H⋯O).
Characterization of π-π stacking interactions.

Main Results:

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Published on: June 20, 2014

The molecule C(9)H(8)N(2)O(2) exhibits a nearly planar conformation.

An intramolecular N-H⋯O hydrogen bond forms a six-membered ring.

Intermolecular N-H⋯O and C-H⋯O hydrogen bonds link molecules into a 2D polymeric network via nine-membered rings.

π-π interactions between aromatic and heterocyclic rings were observed with a centroid-centroid distance of 3.638(2) Å.

Conclusions:

The crystal structure is significantly stabilized by a combination of intra- and intermolecular hydrogen bonding.
The identified hydrogen bonding patterns lead to the formation of a robust two-dimensional supramolecular architecture.
The study highlights the importance of non-covalent interactions in directing crystal packing and forming extended networks.