Back to Search
Start Over
Mechanistic study of fenoprofen photoisomerization to pure (S)-fenoprofen: a DFT study.
- Source :
-
Structural Chemistry . Feb2020, Vol. 31 Issue 1, p115-122. 8p. - Publication Year :
- 2020
-
Abstract
- This work provides a comprehensive DFT study on the conversion mechanism and photoisomerization of the effective and commonly used nonsteroidal anti-inflammatory medicine fenoprofen. The results obtained exhibit that the rearrangement procedure of (R)-fenoprofen to its (S)-enantiomer occurs in [1,3]-hydrogen shifts with inversion of configuration at chiral center C8. According to the computed energies, we can find out that the excitation of (R)-fenoprofen methyl ester in its primary form to the first excited singlet state S1 at λ = 240 nm is the rate-limiting step of photoisomerization of fenoprofen. In order to obtain further insight into the isomerization process occurring upon excitation, this process was studied by scanning the C8-H11 distance for the excited singlet. Our calculations revealed that the isomerization process requires passing a barrier of approximately 84 kcal/mol. Furthermore, the more photostability of (S)-fenoprofen methyl ester than that of its related (R)-enantiomer can be attributed to the − 1.34 kcal/mol of thermodynamic stability of the (S)-fenoprofen methyl ester. [ABSTRACT FROM AUTHOR]
- Subjects :
- *PHOTOISOMERIZATION
*METHYL formate
*CHIRAL centers
*EXCITED states
*ISOMERIZATION
Subjects
Details
- Language :
- English
- ISSN :
- 10400400
- Volume :
- 31
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Structural Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 141339507
- Full Text :
- https://doi.org/10.1007/s11224-019-01382-1