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Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic Sevoflurane: A vibrational circular dichroism study
Author(s) -
Wang Feng,
Polavarapu Prasad L.,
Schurig V.,
Schmidt R.
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10106
Subject(s) - chemistry , vibrational circular dichroism , conformational isomerism , chirality (physics) , enantiopure drug , ab initio , absolute configuration , density functional theory , circular dichroism , sevoflurane , absorption (acoustics) , basis set , ab initio quantum chemistry methods , computational chemistry , stereochemistry , molecule , organic chemistry , catalysis , chiral symmetry , medicine , nambu–jona lasinio model , physics , quantum mechanics , enantioselective synthesis , anesthesia , acoustics , quark
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. Chirality 14:618–624, 2002. © 2002 Wiley‐Liss, Inc.