Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic Sevoflurane: A vibrational circular dichroism study.
1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane, compound B, is a product obtained in the degradation of the anesthetic Sevoflurane. Enantiopure (+)-B was investigated using vibrational circular dichroism (VCD). Experimental absorption and VCD spectra of (+)-B in CDCl(3) solution in the 2,000-900 cm(-1) region are compared with the ab initio predictions of absorption and VCD spectra obtained from density functional theory using B3LYP/6-31G* basis set for different conformers of (S)-1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane. This comparison indicates that (+)-B is of the (S)-configuration in CDCl(3) solution, in agreement with previous literature results. Our results also indicate that this compound adopts six predominant conformations in CDCl(3) solution.
Wang
Feng
F
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Polavarapu
Prasad L
PL
Schurig
V
V
Schmidt
R
R
D018685:Anesthetics, Inhalation / Q000737:chemistry*; D002942:Circular Dichroism; D008738:Methyl Ethers / Q000737:chemistry*; D008968:Molecular Conformation; D000077149:Sevoflurane; D014732:Vibration
D018685:Anesthetics, Inhalation; D008738:Methyl Ethers; D000077149:Sevoflurane