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

Tribenzo

Cantrill1, Fyfe, Heiss

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA.

Organic Letters
|May 18, 2000
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

A Discussion on Amenorrhœal Insanity.

Proceedings of the Royal Society of Medicine·2009
Same author

Artificial Molecular Machines.

Angewandte Chemie (International ed. in English)·2000
Same author

Self-assembly of an amphiphilic

Organic letters·2000
Same author

A photochemically driven molecular-level abacus

Chemistry (Weinheim an der Bergstrasse, Germany)·2000
Same author

Repulsion of resonance states and exceptional points

Physical review. E, Statistical physics, plasmas, fluids, and related interdisciplinary topics·2000
Same author

Comparison of two intraosseous infusion techniques in an EMT training program

Academic emergency medicine : official journal of the Society for Academic Emergency Medicine·2000
Same journal

A General Photocatalytic Decarboxylative Hydrogenation of Carboxylic Acids in Batch and Flow under Metal-Free Conditions.

Organic letters·2026
Same journal

Direct Access to Sulfonamidated-1,4-Benzoquinones via Sulfonamidation of Aryl Alcohol-Derived Quinone Monoacetals.

Organic letters·2026
Same journal

Photo/Cerium Co-Catalyzed Hydroalkylation of Alkynes Via Decarboxylative Ring-Opening of Cyclic Carboxylic Acids.

Organic letters·2026
Same journal

Electrochemical Dehydroxylative Thiolation of Alkyl Alcohols with Disulfides.

Organic letters·2026
Same journal

Molybdenum-Catalyzed Intramolecular Deoxygenative Annulation of 2-(Formamido)aryl Ketones to Access 3-Monosubstituted Oxindoles.

Organic letters·2026
Same journal

Modular Synthesis of Spiroisochromans with Spiro Quaternary Carbon Centers Via TBAT-Promoted Multicomponent Cascade Reactions.

Organic letters·2026
See all related articles

Dibenzylammonium (DBA+) ions form [2]pseudorotaxanes with tribenzo[27]crown-9 (TB27C9) via hydrogen bonding. Substituents on DBA+ ions significantly impact complex stability and formation kinetics.

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Dibenzylammonium (DBA+) ions can form inclusion complexes with macrocyclic hosts.
  • Tribenzo[27]crown-9 (TB27C9) is a macrocycle capable of complexing cationic guests.
  • Hydrogen bonding plays a crucial role in stabilizing supramolecular assemblies.

Purpose of the Study:

  • To investigate the formation and stability of [2]pseudorotaxanes between DBA+ ions and TB27C9.
  • To determine the effect of substituents on the DBA+ phenyl rings on complexation.
  • To analyze the kinetics of complex formation and dissociation.

Main Methods:

  • Synthesis of substituted Dibenzylammonium (DBA+) ions.
  • Complexation studies using tribenzo[27]crown-9 (TB27C9).
  • Spectroscopic techniques (e.g., NMR) to characterize pseudorotaxane formation and stability.

Related Experiment Videos

  • Kinetic experiments to measure complexation and dissociation rates.

    • Main Results:

    • [2]Pseudorotaxanes are successfully formed between DBA+ ions and TB27C9, stabilized by hydrogen bonding.
    • Electron-withdrawing substituents (e.g., pCO2Me) on DBA+ enhance complex stability compared to the parent DBA+ ion.
    • Complexes with substituted DBA+ ions exhibit slower equilibration rates than the parent complex.

    Conclusions:

    • The stability and kinetics of DBA+/TB27C9 pseudorotaxanes are tunable via substituents on the DBA+ ion.
    • Hydrogen bonding is the primary driving force for the observed complexation.
    • This work provides insights into the rational design of host-guest systems with controlled binding affinities and dynamics.