Computational NMR as Useful Tool for Predicting Structure and Stereochemistry of Four‐Membered Sulfur Heterocycles. Issue 19 (27th June 2016)

• Record Type: Journal Article
• Authors: Pisano, Luisa; Degennaro, Leonardo; Carraro, Massimo; Azzena, Ugo; Fanelli, Flavio; Mastrorilli, Piero; Luisi, Renzo
• Is Part Of: European journal of organic chemistry. Issue 19(2016)
• Page Start: 3252
• Page End: 3258
• Publication Date: 2016-06-27
• Subjects: Sulfur heterocycles -- Stereochemistry -- NMR spectroscopy -- DFT calculations; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600372
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : We report a computational NMR study of stereochemically challenging thietane 1‐oxides. Comparison of calculated and experimental data allows to assign structure and stereochemistry to the examined molecules. Computations included full conformational analysis of each thietane, DFT geometry optimizations and GIAO NMR calculations. Among the possible stereoisomers, only the computed structures with the correct stereochemistry were found to fit experimental NMR spectroscopic data. Computational analysis provide useful information on the conformational ring preference not easy to disclose by conventional structural analysis. Abstract : A computational NMR study of stereochemically challenging thietane 1‐oxides is reported. Among the possible stereoisomers, only the computed structures with the correct stereochemistry were found to fit experimental NMR spectroscopic data. Computational analysis provide useful information on the ring conformational preference not easy to disclose by conventional structural analysis.