期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 5, 页码 2879-2883出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo5029425
关键词
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Three decades after the discovery of a strong S-C-P anomeric effect in 2-diphenylphosphinoyl-1,3-dithiane (1) and 2-trimethylphosphonium-1,3-dithiane (4), its definitive interpretation is still lacking. The present study reports DFT geometry optimizations of 1-ax, 1-eq, 4-ax, and 4-eq, which do reproduce the S-C-P anomeric effect in 1 and 4, worth 5.45 and 3.08 kcal/mol, respectively (in chloroform solvent). Weinholds NBO analysis supports the existence of dominant n(X) -> sigma*(C-Y) stereoelectronic interactions that stabilize the axial conformers.
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