Preparation and conformational properties of the novel perfluorodiether, CF3OCF2OCF2C(O)F, a model molecule to study properties of perfluoropolyethers

ROSANA M. ROMANO; JOANNA CZARNOWSKI; CARLOS O. DELLA VÉDOVA

INORGANIC CHEMISTRY

Año: 2001 vol. 40 p. 3039 - 3047

0020-1669

The compound CF3OCF2OCF2C(O)F was prepared by oxidation of hexafluoropropene with molecular oxygen in the gas-phase using CF3OF as initiator. 13C NMR, FTIR, Raman, UV-vis, and mass spectra were obtained and interpreted. The theoretical structure studies were performed by the calculation of the potential energy surfaces, using the results obtained for a smaller related molecule, CF3OCF2C(O)F, as a starting point. A high degree of conformational flexibility of this compound is evidenced by the values of several conformations, varying within the range of 1 kcal/mol. Theoretical calculations predict chain conformations as the most stable molecular forms, as expected from the presence of the anomeric effect. The experimental fundamental vibrational modes are compared with those obtained theoretically, using ab initio and density functional theory methods, HF/6-31+G* and B3LYP/ 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. conformational flexibility of this compound is evidenced by the values of several conformations, varying within the range of 1 kcal/mol. Theoretical calculations predict chain conformations as the most stable molecular forms, as expected from the presence of the anomeric effect. The experimental fundamental vibrational modes are compared with those obtained theoretically, using ab initio and density functional theory methods, HF/6-31+G* and B3LYP/ 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. conformational flexibility of this compound is evidenced by the values of several conformations, varying within the range of 1 kcal/mol. Theoretical calculations predict chain conformations as the most stable molecular forms, as expected from the presence of the anomeric effect. The experimental fundamental vibrational modes are compared with those obtained theoretically, using ab initio and density functional theory methods, HF/6-31+G* and B3LYP/ 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. interpreted. The theoretical structure studies were performed by the calculation of the potential energy surfaces, using the results obtained for a smaller related molecule, CF3OCF2C(O)F, as a starting point. A high degree of conformational flexibility of this compound is evidenced by the values of several conformations, varying within the range of 1 kcal/mol. Theoretical calculations predict chain conformations as the most stable molecular forms, as expected from the presence of the anomeric effect. The experimental fundamental vibrational modes are compared with those obtained theoretically, using ab initio and density functional theory methods, HF/6-31+G* and B3LYP/ 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. point (mp ) -140(5) °C), its boiling point (bp ) 14.5 (1) °C), and the relation between its vapor pressure and the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. the absolute temperature (ln P ) 13.699 - 2023.4/T) were also determined. 6-31+G*, respectively. The density of the compound at ambient temperature (ä ) 1.7(1) g/mL), its melting point (mp ) -140(5) °