Abstract
AbstractOver 60 lignin‐related model compounds were phosphitylated with 2‐chloro‐4,4,5,5‐tetramethyldioxaphospholane, a sterically hindered analogue of 2‐chloro‐1,3,2‐dioxaphospholane used in earlier work, and their 31P chemical shifts were recorded. Excellent resolution between the chemical shifts of phosphitylated carboxylic acids, phenols and aliphatic alcohols was obtained. The correlations of the phosphorus chemical shifts with the chemical environments of lignin‐related phenols using the Hammett principles provided an excellent linear relationship between the resonance substituent constant, σ, and the corresponding 31P NMR chemical shift values for para‐substituted lignin‐related phenols. In addition, a correlation between 31P NMR chemical shifts for ortho‐ and para‐substituted phosphitylated phenols was obtained. A set of empirical parameters that permits the accurate prediction of 31P NMR chemical shifts of lignin‐related phenolic compounds derivatized with 2‐chloro‐4,4,5,5‐tetramethyldioxaphospholane was thus obtained.
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