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NMR Spectroscopy of Aromatic Compounds

NMR Spectroscopy of Aromatic Compounds

Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.

¹H NMR: Complex Splitting

¹H NMR: Complex Splitting

A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied...

2D NMR: Overview of Heteronuclear Correlation Techniques

2D NMR: Overview of Heteronuclear Correlation Techniques

Heteronuclear correlation spectroscopy is an analytical technique that investigates the coupling between different types of nuclei, often a proton and an X-nucleus, such as carbon-13 or nitrogen-15. This method is commonly used in nuclear magnetic resonance (NMR) spectroscopy to gain insights into complex chemical compounds' structural and compositional aspects. A typical heteronuclear correlation spectrum displays X-nucleus chemical shifts on one axis and a proton spectrum on the other...

2D NMR: Overview of Homonuclear Correlation Techniques

2D NMR: Overview of Homonuclear Correlation Techniques

Homonuclear correlation spectroscopy (COSY) is a powerful technique used in Nuclear Magnetic Resonance (NMR) spectroscopy to study the correlations between nuclei of the same type within a molecule. It provides information about scalar couplings between adjacent nuclei, which helps determine connectivity and structural information. There are several COSY variants, each with its unique strengths and experimental parameters.
COSY90 is the standard two-dimensional (2D) COSY experiment that...

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)

2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)

Heteronuclear single-quantum correlation spectroscopy (HSQC) is a 2D NMR technique that reveals one-bond correlations between hydrogen and a heteronucleus. The HSQC experiment is similar to the heteronuclear correlation experiment (HETCOR) but is more sensitive. In the HSQC spectrum, the proton chemical shift is plotted on the horizontal F2 axis, while the 13C chemical shift is plotted on the vertical F1 axis. The corresponding proton and 13C spectra are also shown. The HSQC contour plot does...

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...

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Updated: Jan 8, 2026

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

Structure characterization with NMR molecular networking.

Cailum M K Stienstra^1,2, Jaegun Song¹, David Healey¹

¹Enveda Therapeutics, Inc., Boulder, CO, USA.

Communications Chemistry

|December 17, 2025

Summary

This summary is machine-generated.

We developed NMR molecular networking for analyzing Heteronuclear Single Quantum Coherence (HSQC) spectra, improving compound identification and annotation for natural product discovery.

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Area of Science:

Analytical Chemistry
Structural Biology
Natural Product Chemistry

Background:

Nuclear Magnetic Resonance (NMR) is crucial for structure determination but lacks automated workflows compared to mass spectrometry.
Heteronuclear Single Quantum Coherence (HSQC) is a key 2D-NMR experiment for structure elucidation.

Purpose of the Study:

To introduce and establish NMR molecular networking for HSQC spectra.
To adapt principles of MS² networking (transitivity, dereplication, annotation propagation) for NMR data.
To create a scalable framework for high-throughput annotation in natural product discovery.

Main Methods:

Developed a modified Hungarian distance metric for HSQC peak matching.
Applied NMR molecular networking to HSQC spectra for annotation propagation and compound dereplication.
Integrated graph topology metrics for algorithmic molecular networking to refine rankings and reduce false positives.

Main Results:

The modified metric achieved ~70-80% structural similarity recovery in spectral lookup.
NMR molecular networking accelerated and improved the identification of unknown compounds using experimental natural product spectra.
Algorithmic molecular networking enhanced ranking efficiency and reduced false positives.

Conclusions:

Established the first generalizable framework for NMR molecular networking using HSQC spectra.
Demonstrated the utility of NMR molecular networking for accelerating natural product discovery and drug development.
Provided a scalable solution for high-throughput annotation of complex chemical mixtures.