In:
Israel Journal of Chemistry, Wiley, Vol. 61, No. 11-12 ( 2021-12), p. 743-749
Abstract:
The hydration kinetics of enantiomerically pure propylene oxide (PO, CH 3 *CHCH 2 O) to chiral propylene glycol (PG, CH 3 *CH(OH)CH 2 OH) in aqueous solution have been studied using FTIR while simultaneously monitoring the net chirality of the reaction mixture. The hydration reaction appears to be first‐order in the PO concentration with a rate constant of 0.05 hr −1 . More importantly, the reaction is enantioselective; the product PG retains the chirality of the 2C carbon in PO with ∼2 : 1 selectivity. The fact that there is some inversion of the chirality suggests that the dominant transition state is one in which the 2C−O bond in PO is cleaved, resulting in a close to planar transition state capable of inversion during hydration. If the transition state involved 1C−O cleavage it would retain the rigid chiral center of the PO reactant, preventing significant inversion.
Type of Medium:
Online Resource
ISSN:
0021-2148
,
1869-5868
DOI:
10.1002/ijch.v61.11-12
DOI:
10.1002/ijch.202100098
Language:
English
Publisher:
Wiley
Publication Date:
2021
detail.hit.zdb_id:
2066481-3
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