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Other Nuclides: 31P, 19F, 15N NMR

Other Nuclides: ³¹P, ¹⁹F, ¹⁵N NMR

Many organic, inorganic, and biological molecules contain spin-half nuclei such as nitrogen-15, fluorine-19, and phosphorus-31. As a result, NMR studies of these nuclei have found extensive applications in chemical and biological research.
While fluorine-19 and phosphorous-31 have high natural abundances (100%) and positive gyromagnetic ratios, nitrogen-15 has a low natural abundance and a negative gyromagnetic ratio. However, nitrogen-15 is still preferred over nitrogen-14 (which has a...

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Updated: Jul 5, 2025

An Optimized Protocol for the Efficient Radiolabeling of Gold Nanoparticles by Using a 125I-labeled Azide Prosthetic Group

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Published on: October 10, 2016

¹⁵NRORC: An Azine Labeling Protocol.

Zachary A Tolchin¹, Joel M Smith¹

¹Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, Florida 32306, United States.

Journal of the American Chemical Society

|January 12, 2024

Summary

This summary is machine-generated.

Researchers developed a new method for synthesizing nitrogen-15 (¹⁵N)-labeled azines. This technique enables efficient isotopic labeling of diverse heterocyclic compounds and pharmaceuticals.

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Area of Science:

Organic Chemistry
Isotope Synthesis
Medicinal Chemistry

Background:

Nitrogen-15 (¹⁵N) labeled compounds are crucial for mechanistic studies and pharmaceutical development.
Existing methods for synthesizing ¹⁵N-labeled heterocycles can be limited in scope or efficiency.

Purpose of the Study:

To develop a practical and broadly applicable method for the synthesis of ¹⁵N-labeled azines.
To demonstrate the utility of this method for generating labeled pharmaceuticals.

Main Methods:

Activation of azine heterocycles using electron-deficient arenes.
Substitution of the nitrogen atom with a ¹⁵N-labeled reagent via an ANRORC mechanism.
Application to dearomative synthesis of reduced heterocyclic congeners.

Main Results:

Achieved high isotopic enrichment of ¹⁵N-labeled azines.
Demonstrated the method's applicability to a wide range of azine substrates.
Successfully performed a dearomative formal synthesis of ¹⁵N-solifenacin.

Conclusions:

The described method provides a facile and efficient route to ¹⁵N-labeled azines.
This approach is valuable for synthesizing labeled pharmaceuticals and exploring heterocyclic chemistry.
The method facilitates dearomative access to reduced nitrogen-containing heterocycles.