The shape of ibuprofen in the gas phase

Phys Chem Chem Phys. 2015 Feb 14;17(6):4538-41. doi: 10.1039/c4cp05529b.

Abstract

Ibuprofen's pain-relieving properties arise from its ability to physically block the active site of an enzyme, thus making its structural and conformational properties highly interesting. We here present a conformer-selective high-resolution broadband rotational spectroscopy study of gas-phase ibuprofen. The interpretation of the spectroscopic results is supported by quantum-chemical calculations. We identify four low-energy conformers that differ in the structural arrangement of the isobutyl moiety with respect to the remainder of the molecule. While the isobutyl group shows high structural flexibility - resulting in distinct low-energy conformers - the propanoic acid group favors a stable arrangement.

MeSH terms

  • Analgesics, Non-Narcotic / chemistry*
  • Ibuprofen / chemistry*
  • Molecular Conformation
  • Quantum Theory
  • Thermodynamics
  • Volatilization

Substances

  • Analgesics, Non-Narcotic
  • Ibuprofen