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Downfield chemical shifts at α‐protons and carbons of β‐propiothiolactones
Author(s) -
Lee Hee Bong,
Park HyungYeon,
Lee BonSu,
Kim Young Gyu
Publication year - 2000
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/1097-458x(200006)38:6<468::aid-mrc675>3.0.co;2-f
Subject(s) - chemistry , heteroatom , chemical shift , proton , sulfur , carbon fibers , computational chemistry , crystallography , stereochemistry , organic chemistry , ring (chemistry) , physics , materials science , quantum mechanics , composite number , composite material
Both the α‐protons and carbons of β‐propiothiolactones exhibit atypical downfield chemical shifts. The α‐protons of β‐propiothiolactones with no heteroatom at the α‐position appear at 3.53–5.35 ppm, whereas the α‐carbons appear at 56.9–86.2 ppm. The major cause of the unexpected deshielding effect was rationalized by assuming a through‐space interaction between the occupied orbital of the α‐carbon and the vacant orbital of sulfur. Copyright © 2000 John Wiley & Sons, Ltd.