Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

Stereochemical analysis by solid-state NMR: structural predictions in ambuic acid.

James K Harper1, Dewey H Barich, Jian Z Hu

  • 1Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112, USA.

The Journal of Organic Chemistry
|June 7, 2003
PubMed
Summary
This summary is machine-generated.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Locations of Ca<sup>2+</sup>, Zn<sup>2+</sup>, and Sulfur in Zn-Modified LTA Zeolites During Sulfur Capture and Release.

Inorganic chemistry·2026
Same author

Implantation and Analysis of a Biphasic Bioinspired Osteochondral Chitosan Construct in a Large Animal Model.

ACS biomaterials science & engineering·2026
Same author

Metal-Mediated Nitrogen Doping of Carbon Supports Boosts Hydrogen Production from Ammonia.

Angewandte Chemie (International ed. in English)·2025
Same author

Promising Alloys for Hydrogen Storage in the Compositional Space of (TiVNb)<sub>100-<i>x</i></sub>(Cr,Mo)<sub><i>x</i></sub> High-Entropy Alloys.

ACS applied materials & interfaces·2025
Same author

A solid-state NMR approach for distinguishing between RNH<sub>2</sub> and RNH<sub>3</sub><sup>+</sup> sites.

Solid state nuclear magnetic resonance·2025
Same author

Improving the Prediction of Antioxidant Activity by Identifying High-Probability Conformations with NMR.

Analytical chemistry·2025
Same journal

Concise Synthesis of Pyrano/Benzopyrano[2,3-<i>c</i>]pyrazol-6-ones via Ir/Rh-Catalyzed C-H Activation and Tandem Annulation.

The Journal of organic chemistry·2026
Same journal

Regiodivergent Cyclizations of Donor-Acceptor Cyclopropanes with Hydrazines under Solventless, Mechanochemical Milling.

The Journal of organic chemistry·2026
Same journal

Photocatalytic Decarboxylative Coupling of Diacyl Peroxides with TEMPO.

The Journal of organic chemistry·2026
Same journal

Mechanistic Insights into the Isothiourea-Catalyzed Addition Reaction of a <i>para</i>-Nitrophenyl Ester and an <i>N</i>-Benzylpyridinium Salt.

The Journal of organic chemistry·2026
Same journal

Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Anthrones and 9-Phenanthrols.

The Journal of organic chemistry·2026
Same journal

Copper(II)-Catalyzed <i>N</i>-Arylation and <i>N</i>-Vinylation of Oxadiazolones with Boronic Acids under Mild Conditions.

The Journal of organic chemistry·2026
See all related articles

A new solid-state NMR method predicts ambuic acid

Area of Science:

  • Organic Chemistry
  • Solid-State Chemistry
  • Structural Biology

Background:

  • Ambuic acid's relative stereochemistry remains undetermined.
  • Previous solution NMR studies provided limited structural insights.
  • Crystallization difficulties hinder traditional structural analysis.

Purpose of the Study:

  • To determine the relative stereochemistry of ambuic acid.
  • To develop and validate a novel solid-state NMR approach for structural elucidation.
  • To investigate the potential for intermolecular interactions, such as hydrogen bonding, in ambuic acid.

Main Methods:

  • Utilized solid-state Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Compared experimental chemical shift tensor principal values with computationally derived values for all possible diastereomers.

Related Experiment Videos

  • Modeled molecular conformation and hydrogen-bonding arrangements simultaneously.

    • Main Results:

    • Successfully predicted the relative stereochemistry of ambuic acid.
    • A dimeric structure, stabilized by hydrogen bonding between carboxyl groups, was proposed.
    • The dimeric model significantly improved the fit of carboxyl carbon tensor data compared to a monomeric model.
    • The method also provided insights into lattice details.

    Conclusions:

    • The novel solid-state NMR technique accurately determines relative stereochemistry.
    • Ambuic acid likely exists as a dimer in the solid state, mediated by carboxyl group hydrogen bonding.
    • This method is broadly applicable, especially for challenging, poorly crystalline, or hydrogen-poor materials.