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Methoxyacetone revisited.

Archna Sharma1, Vivek K Gupta1, Igor Reva2

  • 1PG Department of Physics, University of Jammu, Jammu, J&K 180006, India.

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
|December 6, 2023
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Summary
This summary is machine-generated.

Methoxyacetone (MA) exists in four conformations, with the most stable Tt form dominating experimental observations due to conformational cooling. UV photolysis of MA follows Norrish type II and I mechanisms, yielding formaldehyde and carbon monoxide.

Keywords:
(max. 6): MethoxyacetoneConformational coolingDecarbonylationInfrared spectroscopyMatrix isolationPhotochemistry

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Area of Science:

  • Computational Chemistry
  • Spectroscopy
  • Photochemistry

Background:

  • Understanding molecular conformations is crucial for predicting chemical behavior.
  • Methoxyacetone (MA) is a molecule with potential for complex conformational dynamics.
  • Previous experimental work isolated MA in cryogenic matrices.

Purpose of the Study:

  • To computationally investigate the conformational landscape of methoxyacetone (MA).
  • To correlate computational predictions with experimental spectroscopic data.
  • To elucidate the photochemical mechanisms of MA under UV irradiation.

Main Methods:

  • Ab initio (MP2) and Density Functional Theory (DFT/B3LYP) calculations were employed.
  • Conformational analysis involved studying internal rotations around key dihedral angles.
  • Experimental infrared spectroscopy and UV photolysis were used for characterization and reaction studies.

Main Results:

  • Four stable conformations of MA were predicted, with the Trans-trans (Tt) conformer being the most stable.
  • Experimental infrared spectroscopy detected only the Tt conformer, attributed to conformational cooling during matrix deposition.
  • UV photolysis (300-260 nm) of MA proceeded via Norrish type II and type I mechanisms, producing formaldehyde and carbon monoxide.

Conclusions:

  • Computational methods accurately predict the conformational preferences of MA.
  • Conformational cooling explains the experimental observation of a single conformer.
  • The photolysis of MA provides insights into its reaction pathways under UV light, highlighting Norrish mechanisms.