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Long range substituent effects relfected in the 13 C NMR spectra of allyl alcohols and their derivatives
Author(s) -
Wenkert Ernest,
Gašić Miroslav J.,
Hagaman Edward W.,
Kwart L. D.
Publication year - 1975
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270070112
Subject(s) - chemistry , substituent , chemical shift , double bond , acylation , polarization (electrochemistry) , spectral line , carbon fibers , medicinal chemistry , photochemistry , nmr spectra database , organic chemistry , catalysis , physics , materials science , astronomy , composite number , composite material
Abstract Acylation of allyl alcohols induces strong carbon shifts, shielding γ and deshielding δ effects. These shifts are a consequence of through‐bond polarization of the olefinic carbons. Allyl ethers show similar, but milder perturbations. The olefinic carbon shifts reveal a strong concentration dependence. This effect, in greatly reduced form, is also observed in non‐oxygenated alkenes. Hydrogen bonding by alcohols enhances the chemical shift difference in olefinic carbon pairs by increased polarization.