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Proton NMR spectroscopy of asymmetric benzylamines. The long‐range effects of an asymmetric environment
Author(s) -
JagurGrodzinski Joseph
Publication year - 1982
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.1270180410
Subject(s) - diastereomer , chemistry , enantiomer , molecule , proton , nuclear magnetic resonance spectroscopy , proton nmr , chemical shift , stereochemistry , spectroscopy , medicinal chemistry , organic chemistry , physics , quantum mechanics
1 H NMR Spectra of the asymmetric benzylamines N ‐benzyl‐ N ‐butyl‐2‐hydroxy‐1,3‐propandiamine, N ‐benzyl‐ N ‐(2‐ethylhexyl)‐2‐hydroxy‐1,3‐propandiamine, N ‐benzyl‐ N ‐butyl‐2,3‐epoxypropanamine and N ‐benzyl‐ N ‐(2‐ethylhexyl)‐2,3‐epoxypropanamine, were analysed. A pronounced non‐equivalance of the benzylic hydrogens is induced by asymmetric carbons in γ position with respect to the benzylic group. [Δδ=0.2–0.3 ppm; J (AB)∼13.5 Hz]. Two sets of AB patterns were observed when two asymmetric carbons were present in the same molecule. RS + SR Diastereomers can thus be distinguished from the RR + SS enantiomers.