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

Substituent effects on benzdiyne: a density functional theory study.

Sundaram Arulmozhiraja1, Tadatake Sato, Akira Yabe

  • 1Photoreaction Control Research Center, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan.

The Journal of Organic Chemistry
|June 21, 2003
PubMed
Summary

Density functional theory (DFT) investigated how substituents affect benzdiyne properties. Electron-withdrawing groups destabilized benzdiyne derivatives, while electron-donating groups stabilized them, with field effects dominating resonance effects.

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

Construction and commissioning of mid-infrared self-amplified spontaneous emission free-electron laser at compact energy recovery linac.

The Review of scientific instruments·2021
Same author

Elucidation of Molecular Mechanism of a Selective PPARα Modulator, Pemafibrate, through Combinational Approaches of X-ray Crystallography, Thermodynamic Analysis, and First-Principle Calculations.

International journal of molecular sciences·2020
Same author

Desensitization to mid-spatial-frequency surface errors.

Optics express·2019
Same author

Hepatocyte ELOVL Fatty Acid Elongase 6 Determines Ceramide Acyl-Chain Length and Hepatic Insulin Sensitivity in Mice.

Hepatology (Baltimore, Md.)·2019
Same author

Total Synthesis of Termicalcicolanone A via Organocatalysis and Regioselective Claisen Rearrangement.

Organic letters·2019
Same author

Dual conformation of the ligand induces the partial agonistic activity of retinoid X receptor α (RXRα).

FEBS letters·2018

Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • Benzdiynes are reactive intermediates with unique electronic structures.
  • Understanding substituent effects is crucial for predicting their stability and reactivity.
  • Previous studies have explored various aspects of benzdiyne chemistry.

Purpose of the Study:

  • To investigate the impact of diverse substituents on benzdiyne properties using DFT.
  • To analyze the relative stabilities and electronic characteristics of substituted benzdiynes.
  • To correlate theoretical findings with experimental spectroscopic data.

Main Methods:

  • Density Functional Theory (DFT) calculations employing the B3LYP hybrid functional.
  • Utilized split-valence 6-31G(d) and cc-pVTZ basis sets for structural and vibrational analyses.

Related Experiment Videos

  • Employed isodesmic reactions to determine relative stabilities and heats of formation.

    • Main Results:

    • Electron-withdrawing substituents destabilized benzdiynes, while electron-donating groups stabilized them.
    • Field/inductive effects were found to be more influential than resonance effects.
    • Calculated asymmetric nu(Ctbd1;C) stretching frequencies were near 1500 cm⁻¹, consistent with experimental IR data.

    Conclusions:

    • Substituent type significantly modulates benzdiyne stability and electronic properties.
    • DFT calculations provide reliable predictions for benzdiyne behavior.
    • The study offers insights into the vibrational spectroscopy of substituted benzdiynes.