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Hindered rotation and electronic distribution in thiocarbamates
Author(s) -
El Migirab Saadeddin,
Jadot Joseph,
Laszlo Pierre,
Stockis Armel
Publication year - 1976
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.1270080210
Subject(s) - thiocarbamate , thiocarbamates , chemistry , delocalized electron , rotation (mathematics) , carbon atom , crystallography , stereochemistry , ring (chemistry) , organic chemistry , mathematics , geometry
We wish to report here the isolation of methyl N ‐( p ‐methoxybenzyl)thiocarbamate, a natural product extracted from Pentadiplandra brazzena Bailli , and the synthesis of its homologue, benzyl N ‐(2‐phenylethyl)thiocarbamate. The barrier to internal rotation calculated from a complete lineshape analysis of the temperature dependent 1 H n.m.r. spectra is discussed. The extent of delocalization on the three N, S and O substituents on the central trigonal carbon atom is gauged from a double labelling experiment.