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Related Experiment Videos

Chemoselectivities in acetalization, thioacetalization, oxathioacetalization and azathioacetalization.

Ram Kinkar Roy1, Priyanka Bagaria, Sarala Naik

  • 1Department of Chemistry, Birla Institute of Technology and Science (BITS), Pilani-333 031, Rajasthan, India. rkoy2@rediffmail.com

The Journal of Physical Chemistry. A
|February 10, 2006
PubMed
Summary

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This study compares cyclic acetal yields using aldehydes and various bisnucleophiles. Theoretical calculations, including atomic charges and electrophilicity, explain observed trends and reaction mechanisms.

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Acetal formation is a fundamental organic reaction.
  • Understanding factors influencing acetal yield is crucial for synthetic chemistry.

Purpose of the Study:

  • To experimentally and theoretically compare the relative yields of cyclic acetals.
  • To elucidate the reaction mechanisms governing acetal formation using computational descriptors.

Main Methods:

  • Experimental synthesis of cyclic acetals from substituted benzaldehydes and bisnucleophiles.
  • Theoretical calculations of atomic charges and global electrophilicity (w).
  • Application of the Hard-Soft Acid-Base (HSAB) theory.

Main Results:

  • Acetal yields for p-(NO2)C6H4CHO followed the trend (S,N) > (S,O) > (O,O) > (S,S).

Related Experiment Videos

  • Acetal yields for p-(OH)C6H4CHO followed the trend (S,N) ≈ (S,S) > (S,O) > (O,O).
  • Theoretical descriptors correlated well with experimental observations, explaining yield variations.

    • Conclusions:

    • Global electrophilicity (w) values predict acetal yields.
    • Atomic charges and local softness explain reaction mechanisms.
    • Reaction control (charge vs. orbital) depends on the specific substrates and nucleophiles involved.