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- Title
Differentiation and identification of enantiomers by nuclear magnetic resonance spectroscopy with support of quantum mechanical computations.
- Authors
Brzezicki, Artur; Garbacz, Piotr
- Abstract
We report nuclear magnetic resonance studies of two chiral building blocks of solifenacin, phenyltetrahydroisoquinoline and quinuclidinol, in which chiral solvating agents, Mosher's acid, and Pirkle's alcohol were used for spectral discrimination between enantiomers of solifenacin constituents. Based on the constraints following from measurements of the nuclear Overhauser effect, structures of phenyltetrahydroisoquinoline and Pirkle's alcohol solvates were found. Next, shifts of nuclear magnetic resonance signals of phenyltetrahydroisoquinoline due to the application of Pirkle's alcohol were computed using density functional theory methods. The computed carbon‐13 shifts reproduce those determined experimentally, allowing us to attribute the absolute configuration to phenyltetrahydroisoquinoline enantiomers without the need for the use of empirical rules.
- Subjects
QUANTUM computing; NUCLEAR magnetic resonance; NUCLEAR magnetic resonance spectroscopy; OVERHAUSER effect (Nuclear physics); DENSITY functionals; ENANTIOMERS; DENSITY functional theory; CHEMICAL shift (Nuclear magnetic resonance)
- Publication
Chirality, 2024, Vol 36, Issue 1, p1
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.23623