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

Are oxocarbon dianions aromatic?

Schleyer1, Najafian, Kiran

  • 1Computational Chemistry Annex, University of Georgia, Athens, Georgia 30602-2525, and Institut fur Organische Chemie der Universitat Erlangen-Nurnberg, Henkestrasse 42, D-91054 Erlangen, Germany.

The Journal of Organic Chemistry
|May 18, 2000
PubMed
Summary

Oxocarbon dianions exhibit varying degrees of aromaticity, with C3O3(2-) being doubly aromatic. Cyclic electron delocalization was assessed using structural, energetic, and magnetic criteria for these compounds.

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

Pseudo Groove's sign: A novel finding in cutaneous tuberculosis.

Indian journal of sexually transmitted diseases and AIDS·2026
Same author

Efficient molecular solar thermal energy storage in self-assembled columnar triethynylbenzene-azobenzene systems.

Chemical communications (Cambridge, England)·2026
Same author

Netherton Syndrome Masquerading as Pustular Psoriasis.

Indian dermatology online journal·2026
Same author

Viscosity-sensitive NIR probe for detecting cellular state transitions in Normal, Cancer and apoptotic cells.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2026
Same author

Microalbuminuria in normotensive nondiabetic overweight and obese versus nonobese adults.

Journal of family medicine and primary care·2025
Same author

Design and synthesis of new 1,4-naphthoquinones appended sulfenylated thiazoles as cyclooxygenase II inhibitors: Exploring the utility in the development of anticancer agents.

Bioorganic chemistry·2025

Area of Science:

  • Theoretical Chemistry
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Aromaticity is a key concept in chemistry, influencing molecular stability and reactivity.
  • Oxocarbons and their dianions represent a class of compounds with potential aromatic character.
  • Understanding electron delocalization is crucial for predicting molecular properties.

Purpose of the Study:

  • To assess the cyclic electron delocalization and aromaticity of oxocarbon dianions (CnOn(2-)) and their neutral counterparts (CnOn) for n = 3-6.
  • To investigate the contributions of sigma and pi electron delocalization to aromaticity.
  • To analyze the influence of ring size on aromatic properties.

Main Methods:

  • Utilized structural, energetic, and magnetic criteria to evaluate aromaticity.

Related Experiment Videos

  • Employed the Individual Gauge for Localized Orbitals (IGLO) method to compute localized orbital contributions.
  • Calculated nucleus-independent chemical shifts (NICS) to probe electron delocalization.

    • Main Results:

    • C3O3(2-) exhibits double aromaticity (sigma and pi delocalization).
    • C4O4(2-) shows moderate aromaticity, while C5O5(2-) and C6O6(2-) display reduced aromaticity.
    • The pi contribution to NICS decreases with increasing ring size in oxocarbon dianions.
    • Neutral C4O4 displays cyclic electron delocalization via partial sigma bond occupancy.
    • All neutral oxocarbons possess highly exothermic dissociation energies.

    Conclusions:

    • Aromaticity in oxocarbon dianions is size-dependent, with smaller rings being more aromatic.
    • Both sigma and pi electron delocalization contribute to the aromatic character of these systems.
    • Neutral oxocarbons, despite delocalization, are thermodynamically unstable towards dissociation.