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Following the oxidation state of organosulfur compounds with NMR: Experimental data versus DFT calculations and database-powered NMR prediction
Jagiellonian Univ, Fac Pharm, Dept Organ Chem, Med Coll, Ul Med 9, PL-30688 Krakow, Poland..
KTH, School of Industrial Engineering and Management (ITM), Materials Science and Engineering.
Jagiellonian Univ, Fac Pharm, Dept Organ Chem, Med Coll, Ul Med 9, PL-30688 Krakow, Poland..
Jagiellonian Univ, Fac Pharm, Dept Organ Chem, Med Coll, Ul Med 9, PL-30688 Krakow, Poland..
2020 (English)In: Journal of Molecular Structure, ISSN 0022-2860, E-ISSN 1872-8014, Vol. 1202, article id 127346Article in journal (Refereed) Published
Abstract [en]

The thioether-sulfoxide-sulfone oxidation ladder is a feature significant for drug synthesis and medicinal chemistry. The studies presented herein showed the suitability of various NMR prediction methods for following the oxidation state of sulfur. Method accuracy and the value of additional information were evaluated. As a model for the study, a small set of novel terminal alkynes containing a thioether, sulfoxide or sulfone fragment and an n-alkyl chain was used. The compounds have been synthesized and investigated using H-1 and C-13 NMR spectroscopy, with 2D-NMR spectra providing the certainty of assignment. The experimental NMR spectra were confronted to chemical shifts calculated using the DFT-GIAO method and two generally available database-powered NMR prediction algorithms. The ability to correctly determine the oxidation state of sulfur using experimental and predicted NMR data is discussed, as well as the predictive power and accuracy of the prediction methods used. Additionally, the structure and conformational dynamics of the synthesized compounds are discussed using the DFT-based calculations results.

Place, publisher, year, edition, pages
Elsevier, 2020. Vol. 1202, article id 127346
Keywords [en]
Terminal alkynes, Sulfones, Sulfoxides, NMR prediction, GIAO
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-266217DOI: 10.1016/j.molstruc.2019.127346ISI: 000501486700038Scopus ID: 2-s2.0-85075497320OAI: oai:DiVA.org:kth-266217DiVA, id: diva2:1383139
Note

QC 20200107

Available from: 2020-01-07 Created: 2020-01-07 Last updated: 2020-01-07Bibliographically approved

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