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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...

¹H NMR: Long-Range Coupling

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...

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.

Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the...

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...

C–C Bond Formation: Aldol Condensation Overview

C–C Bond Formation: Aldol Condensation Overview

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.

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

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Published on: January 21, 2020

Natural Products Containing an N-N Bond (2013-2025).

Qiannan Xiao¹, Menghua Wang¹

¹Department of Natural Medicinal Chemistry, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing 211198, China.

Journal of Natural Products

|April 13, 2026

Summary

This summary is machine-generated.

Nitrogen-nitrogen (N-N) bond natural products are a growing class of metabolites. This review covers 169 N-N bond compounds discovered between 2013-2025, detailing their structures and activities.

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Published on: May 26, 2019

Area of Science:

Natural Product Chemistry
Organic Chemistry
Biochemistry

Background:

Nitrogen-nitrogen (N-N) bond-containing natural products represent a unique and expanding class of metabolites.
These compounds are increasingly recognized for their novel structures, diverse functions, and distinct biosynthetic pathways.

Purpose of the Study:

To review the discovery and characteristics of N-N bond-containing natural products.
To summarize structural features, biological activities, and biosynthetic logic of these compounds.

Main Methods:

Literature review of scientific publications from early 2013 to late 2025.
Systematic organization of 169 identified N-N bond natural products based on structural frameworks.

Main Results:

Compilation of 169 N-N bond natural products reported within the specified timeframe.
Detailed summary of the structural diversity and biological activities of these compounds.
Analysis of the unique biosynthetic logic underlying N-N bond formation in natural products.

Conclusions:

Nitrogen-nitrogen bond natural products are a significant and evolving area of research.
Understanding their structural originality and functional diversity is crucial for future discoveries.
Further investigation into their biosynthetic pathways may unlock novel chemical scaffolds and applications.