Abstract：
:The mechanism and origin of selectivity for [3 + 2]-cycloaddition (32CA) reactions between thioketone and carbohydrate-derived nitrones in THF were investigated by using the density functional theory (DFT) at the M06-2X/6-311+G(d,p)//M06-2X/6-31+G(d,p) level of theory combined with the solvation SMD model. The calculated results revealed that the 32CA reactions proceed through the asynchronous one-step manner. For the chemoselectivity in thioketone, the C=S bond as a dipolarophile attacking three-atom-component (TAC) nitrone in reactivity was more preferential than the C=O bond. The theoretical results also confirmed the stereoselectivity of two 32CA reactions of thioketone with carbohydrate-derived nitrones with the anti-form product being more favored than the syn-form product, and the predicted anti/syn product ratios are in agreement with the experimental ones in literature. Furthermore, the analysis of the conceptual density functional theory reactivity indices showed that the 32CA reactions have polar character. Weak noncovalent interaction and Parr function analyses are used to reveal the origin of the stereoselectivity. Graphical abstract [3 + 2]-cycloaddition reactions between thioketone and carbohydrate-derived nitrones.
journal_name
J Mol Modeljournal_title
Journal of molecular modelingauthors
Yang J,Zhang Y,Yang Y,Xue Ydoi
10.1007/s00894-019-4104-6subject
Has Abstractpub_date
2019-07-02 00:00:00pages
209issue
7eissn
1610-2940issn
0948-5023pii
10.1007/s00894-019-4104-6journal_volume
25pub_type
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