Assignment of NMR spectral data of diastereomeric tetrahydrofuranyl acetals directly from their mixture by spectral simulation

Autor: Nešić Milan S., Nešić Milica D., Radulović Niko S.
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Journal of the Serbian Chemical Society, Vol 89, Iss 1, Pp 1-11 (2024)
Druh dokumentu: article
ISSN: 0352-5139
1820-7421
23061405
99742209
DOI: 10.2298/JSC230614054N
Popis: In this study, an NMR spectral analysis of the mixture of diastereomeric acetals, synthesized from 2,3-dihydrofurane and a racemic mixture of citronellol, was performed. 1H-NMR full spin analysis was achieved by manually adjusting δH and J values (previously calculated using the Spartan software) to fit the experimentally available values, followed by further optimization using MestreNova software. The simulated 1H- and 13C-NMR spectra of individual diastereomers, as well as their superimposed and summed spectra, were compared with the obtained experimental spectra. Spin simulation of proton signals was particularly useful for the assignment of the diastereotopic protons of tetrahydrofuranyl moiety and diastereomer discrimination. The NMR spectral data of individual diastereomers – chemical shifts, coupling constants, HMBC and NOESY interactions were systematized in appropriate tables and schemes. To the best of our knowledge, this is for the first time that the complete assignment of tetrahydrofuranyl moiety was performed, and the data obtained herein may be of great importance for the utilization of this protecting group in the future.
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