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Fluorination effects probed in 4-fluoroacetophenone and its monohydrate.

Xiujuan Wang1, Jiayi Li1, Juncheng Lei1

  • 1School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, 401331, Chongqing, China. qian.gou@cqu.edu.cn.

Physical Chemistry Chemical Physics : PCCP
|September 15, 2023
PubMed
Summary

Fourier transform microwave spectroscopy revealed one conformer of 4-fluoroacetophenone and two isomers of its monohydrate. Hydrogen bonding and fluorination effects on molecular structure and methyl group rotation were analyzed.

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Area of Science:

  • Molecular Spectroscopy
  • Quantum Chemistry
  • Supramolecular Chemistry

Background:

  • 4-Fluoroacetophenone is a key molecule in organic chemistry.
  • Understanding the non-covalent interactions in its hydrated forms is crucial for predicting its behavior.

Purpose of the Study:

  • To investigate the rotational spectra of 4-fluoroacetophenone monomer and its monohydrate.
  • To determine the structures and analyze the intermolecular interactions of the observed species.
  • To study the effect of fluorination on molecular properties.

Main Methods:

  • Fourier transform microwave spectroscopy
  • Quantum chemical calculations
  • Analysis of 13C isotopologues

Main Results:

  • One conformer of 4-fluoroacetophenone and two isomers of 4-fluoroacetophenone-H2O were identified.
  • Both isomers are stabilized by O-H⋯O and C-H⋯O hydrogen bonds.
  • Fluorination effects on geometry, non-covalent interactions, and methyl internal rotation barriers were analyzed.

Conclusions:

  • Accurate structural determination of 4-fluoroacetophenone monomer was achieved.
  • The stabilization mechanisms and conformational preferences of the monohydrate were elucidated.
  • The study provides insights into the influence of fluorine substitution on molecular interactions.