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Pseudohalogen chemistry. VIII —Substituent constants ( Z ) for the thiocyanato group in the estimation of the chemical shifts of vinyl protons in α,β‐unsaturated thiocyanates
Author(s) -
Guy Robert G.
Publication year - 1988
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/mrc.1260260610
Subject(s) - chemistry , substituent , steric effects , additive function , chemical shift , group (periodic table) , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , mathematical analysis , mathematics
Substituent constants for the thiocyanato group ( Z gem SCN= 0.94, Z cis SCN= 0.45 and Z trans SCN = 0.41) have been derived by an additivity procedure, and shown to reproduce the chemical shifts of vinyl protons in a wide variety of α,β‐unsaturated thiocyanates with an accuracy of ±0.30 ppm in 94% of the cases studied. Deviations due to t Bu and COR groups are discussed in terms of steric and field effects.