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Updated: May 29, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Chlorodifluoroacetyl cyanide, ClF2CC(O)CN: synthesis, structure, and spectroscopic characterization
Luis A Ramos1, Sonia E Ulic, Rosana M Romano
1CEQUINOR (UNLP-CONICET), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, 1900 La Plata, República Argentina.
A novel molecule, difluorochloroacetyl cyanide, was characterized using multiple spectroscopic methods. Researchers identified two stable conformers, with the gauche form being more stable, indicating its potential as a new chemical precursor.
Area of Science:
- * Molecular spectroscopy
- * Quantum chemistry
- * Organic synthesis
Background:
- * Acyl cyanides are valuable in preparative chemistry.
- * Understanding molecular structure and properties is crucial for developing new chemical precursors.
Purpose of the Study:
- * To characterize the novel molecule difluorochloroacetyl cyanide (ClF(2)CC(O)CN).
- * To investigate its conformational properties and electronic structure.
- * To assess its potential as a precursor in chemical synthesis.
Main Methods:
- * Infrared (IR) and Raman spectroscopy
- * Nuclear Magnetic Resonance (NMR) spectroscopy ((19)F and (13)C)
- * Photoelectron Spectroscopy (PES) and Photoionization Mass Spectrometry (PIMS)
- * Gas Electron Diffraction (GED)
- * Quantum chemical calculations
Main Results:
- * Difluorochloroacetyl cyanide exists in two conformers (gauche and syn) in gas and liquid phases.
- * The gauche conformer is more stable by 1.3 kcal mol(-1).
- * The first vertical ionization energy is 12.0 eV, attributed to oxygen lone pair electron ejection.
- * Valence electronic properties and ionization/dissociation pathways were elucidated.
Conclusions:
- * Difluorochloroacetyl cyanide has been thoroughly characterized.
- * Its conformational preferences and electronic properties are now understood.
- * The molecule shows promise as a new precursor in preparative chemistry due to its unique structure and reactivity.
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