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

The gem-dimethyl effect revisited.

Steven M Bachrach1

  • 1Department of Chemistry, Trinity University, 1 Trinity Place, San Antonio, Texas 78212 sbachrach@trinity.edu.

The Journal of Organic Chemistry
|February 19, 2008
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

The Topology of Molecules with Twelve Fused Phenyl Rings ([12]Circulenes): Rings, Infinitenes, and Möbius Infinitenes.

The Journal of organic chemistry·2023
Same author

Cycloparaphenylene Möbius trefoils.

Chemical communications (Cambridge, England)·2020
Same author

Cycloparaphenylene Lemniscates and Trefoils.

The Journal of organic chemistry·2019
Same author

Planar rings in nano-Saturns and related complexes.

Chemical communications (Cambridge, England)·2019
Same author

Chiral Superbases with Extended Hydrogen Bond Networks.

The Journal of organic chemistry·2019
Same author

"Planetary Orbit" Systems Composed of Cycloparaphenylenes.

The Journal of organic chemistry·2016
Same journal

Switchable <i>N</i>-Haloethylation and C-H Halogenation of NH-Enaminones with 1,2-Dihaloethanes.

The Journal of organic chemistry·2026
Same journal

Lewis Acid-Catalyzed Cascade Ring Expansion and Intramolecular Friedel-Crafts Type Cyclization of α-Dithioacetyl Propargyl Alcohols: Access to <i>S</i>,<i>S</i>-Heterocycle-Fused Benzofulvenes and 3-Benzylidene-1-indanones.

The Journal of organic chemistry·2026
Same journal

Photocatalytic Decarboxylation of Carboxylic Acids to Construct Unnatural Amino Acids and Peptides-Containing Piperidine Rings.

The Journal of organic chemistry·2026
Same journal

TABF as a Double Proton Sponge: Steric Preorganization versus Antiaromatic Destabilization.

The Journal of organic chemistry·2026
Same journal

Copper-Catalyzed Radical Sulfonylative Cyclization of <i>o</i>-Vinylanilides with Sulfonyl Chlorides for the Synthesis of Sulfonylated 4<i>H</i>-Benzo[<i>d</i>][1,3]oxazines.

The Journal of organic chemistry·2026
Same journal

Photochemical Ni-Catalyzed Cross-Coupling of Aryl Bromides with Hydrazides.

The Journal of organic chemistry·2026
See all related articles

The gem-dimethyl effect in 1,1-dimethylcyclobutane has no significant enthalpic component. Ring strain energy calculations confirm this finding, impacting understanding of molecular stability.

Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • The gem-dimethyl effect describes steric interactions in molecules with geminal dimethyl groups.
  • Understanding the energetic contributions to this effect is crucial for predicting molecular stability and reactivity.
  • Cyclobutane derivatives provide a model system for studying ring strain and substituent effects.

Purpose of the Study:

  • To computationally determine the ring strain energy of 1,1-dimethylcyclobutane.
  • To investigate the enthalpic contribution of the gem-dimethyl effect in this system.
  • To elucidate the energetic basis of the gem-dimethyl effect in strained rings.

Main Methods:

  • Utilized a variety of computational chemistry methods.

Related Experiment Videos

  • Calculated the ring strain energy for 1,1-dimethylcyclobutane.
  • Analyzed the enthalpic components contributing to the observed strain.

    • Main Results:

    • Ring strain energy computations were performed using multiple theoretical approaches.
    • No significant enthalpic component was identified for the gem-dimethyl effect in 1,1-dimethylcyclobutane.
    • The results indicate that steric strain, not enthalpy, is the primary factor.

    Conclusions:

    • The gem-dimethyl effect in 1,1-dimethylcyclobutane is largely enthalpically neutral.
    • Ring strain energy is a key metric for assessing the energetic impact of substituents in cyclic systems.
    • This finding refines the understanding of substituent effects in strained organic molecules.