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Racemization mechanism of lithium tert-butylphenylphosphido-borane: A kinetic insight.
- Source :
-
Chirality [Chirality] 2022 Jan; Vol. 34 (1), pp. 27-33. Date of Electronic Publication: 2021 Nov 03. - Publication Year :
- 2022
-
Abstract
- The racemization mechanism of tert-butylphenylphosphido-borane is investigated experimentally and theoretically. Based on this converging approach, it is shown, first, that several phosphido-borane molecular species coexist at the time of the reaction and, second, that one particular of both initially assumed reactive routes most significantly contribute to the overall racemization process. From our converging modeling and experimental measurement, it comes out that the most probable species to be here encountered is a phosphido-borane-Li (THF) <subscript>2</subscript> neutral solvate, whose P-stereogenic center monomolecular inversion through a Y-shaped transition structure (Δ <subscript>r</subscript> G° <superscript>≠</superscript> : 81 kJ mol <superscript>-1</superscript> ) brings the largest contribution to the racemization process.<br /> (© 2021 Wiley Periodicals LLC.)
- Subjects :
- Kinetics
Lithium
Stereoisomerism
Boranes
Subjects
Details
- Language :
- English
- ISSN :
- 1520-636X
- Volume :
- 34
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Chirality
- Publication Type :
- Academic Journal
- Accession number :
- 34734430
- Full Text :
- https://doi.org/10.1002/chir.23383