Aryl Fluoroalkyl Sulfoxides: Optical Stability and p K a   Measurement | Zendy

Messara Amélia | Zendy; Vanthuyne Nicolas | Zendy; Diter Patrick | Zendy; Elhabiri Mourad | Zendy; Panossian Armen | Zendy; Hanquet Gilles | Zendy; Magnier Emmanuel | Zendy; Leroux Frédéric R. | Zendy

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Aryl Fluoroalkyl Sulfoxides: Optical Stability and p K a Measurement

Author(s) -

Messara Amélia,

Vanthuyne Nicolas,

Diter Patrick,

Elhabiri Mourad,

Panossian Armen,

Hanquet Gilles,

Magnier Emmanuel,

Leroux Frédéric R.

Publication year - 2021

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202100816

Subject(s) - chemistry , enantiomer , aryl , trifluoromethyl , titration , thermal stability , enantiomeric excess , medicinal chemistry , sulfoxide , organic chemistry , enantioselective synthesis , catalysis , alkyl

The enantiomeric separation of aryl trifluoromethyl and difluoromethyl sulfoxides was realized via chiral chromatography. The configurational stability of each set of enantiomers was then studied by thermal enantiomerization. The Δ G ≠ values obtained cover a range of 38.2–41.0 kcal mol −1 at 214 °C, thus demonstrating their optical stability at room temperature. However, a shorter half‐life time has been observed for difluoromethyl sulfoxides. Furthermore, the acidities of six aryl difluoromethyl sulfoxides were determined in DMSO by an overlapping indicator method using UV‐visible spectrophotometric titrations. The p K a values fall in range of 20.3–22.5 and differ by about 10 log units compared to non‐fluorinated analogues.

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