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13 C NMR spectra and structure of mono‐, di‐ and trimethoxyphenylethylamines and amphetamines
Author(s) -
Bailey Keith,
Legault Donald
Publication year - 1983
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/omr.1270210611
Subject(s) - side chain , alkane stereochemistry , conformational isomerism , chemistry , chemical shift , ring (chemistry) , lone pair , stereochemistry , crystallography , nmr spectra database , spectral line , molecule , crystal structure , organic chemistry , physics , polymer , astronomy
Carbon‐13 and proton chemical shifts of mono‐, di‐ and trimethoxylated phenylethylamines (PEAs) and their hydrochlorides were determined and the signals were assigned and are reported. The data are interpreted to indicate that the side‐chains of PEA derivatives and amphetamine salts have the amino and aromatic moieties predominantly trans (antiperiplanar), that ‘sandwiched’ OCH 3 groups and side‐chains are forced out of the ring plane and that planar ortho ‐OCH 3 groups have their electron lone pairs oriented toward the side‐chain and partially stabilize gauche rotamers. It is suggested that the location and density of electronic charges just outside the aromatic ring will significantly affect interactions with putative receptors.