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

Why Doesn't all-trans-1,2,3,4,5,6-Hexaspiro(THF)cyclohexane complex metal ions?

Rablen1, Paquette, Borden

  • 1Department of Chemistry, Swarthmore College, 500 College Avenue, Swarthmore, Pennsylvania 19081-1397, Department of Chemistry, The Ohio State University, Evans Chemistry Labs, Columbus, Ohio 43210, and Department of Chemistry, University of Was.

The Journal of Organic Chemistry
|January 10, 2001
PubMed
Summary

All-trans-hexaspiro(THF)cyclohexane favors an equatorial conformation due to the gauche effect and high energetic costs of axial alkoxy groups. These factors overcome typical preferences for alkyl substituents in cyclohexane derivatives.

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

Synthesis and conformational properties of several maximally substituted hexa(spirotetrahydrofuranyl)cyclohexanes. Assessment Of the pronounced bias of the all-trans D(3)(d)()-symmetric isomer for total equatorial oxygen occupancy

The Journal of organic chemistry·2001
Same author

Convergent regiodirected assembly of 2,3-disubstituted furans

Organic letters·2000
Same author

Computational analysis of the solvent effect on the barrier to rotation about the conjugated C-N bond in methyl N, N-dimethylcarbamate

The Journal of organic chemistry·2000
Same author

Radical and anionic response of N-(Bromomethanesulfonyl)-substituted alpha,alpha'-bridged piperidine substrates

The Journal of organic chemistry·2000
Same author

Selected topics related to occupational exposures. Part II. Occupational infectious diseases

Disease-a-month : DM·2000
Same author

Selected topics related to occupational exposures. Part III. Occupational dermatology

Disease-a-month : DM·2000

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Cyclohexane derivatives typically favor equatorial substituents due to steric hindrance.
  • Alkoxy substituents usually prefer equatorial positions, but this study explores exceptions.

Purpose of the Study:

  • To investigate the conformational preferences of all-trans-hexaspiro(THF)cyclohexane.
  • To elucidate the factors driving the unusual equatorial preference of alkoxy substituents in this molecule.

Main Methods:

  • Ab initio calculations
  • Density functional theory (DFT) calculations
  • Conformational analysis of cyclohexane derivatives with spiro(THF) units.

Main Results:

  • All-trans-hexaspiro(THF)cyclohexane strongly favors the all-oxygen-equatorial conformer.

Related Experiment Videos

  • The gauche effect favors di-O-equatorial arrangements when oxygen atoms are adjacent.
  • Axial alkoxy substituents incur a higher energetic cost (approx. 2 kcal/mol) compared to alkyl substituents in 1,3-diaxial interactions.

    • Conclusions:

    • The conformational bias in all-trans-hexaspiro(THF)cyclohexane is driven by multiple gauche interactions and the significant energetic penalty of axial alkoxy groups.
    • These findings challenge the typical understanding of substituent preferences in cyclohexane systems.