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Utility of 1 H/ 2 H isotope shifts for the 13 C NMR assignments of indole derivatives
Author(s) -
MoralesRíos M. S.,
JosephNathan P.
Publication year - 1989
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.1260270114
Subject(s) - chemistry , deuterium , indole test , kinetic isotope effect , deuterium nmr , isotope , carbon 13 nmr , chemical shift , nuclear magnetic resonance spectroscopy , carbazole , medicinal chemistry , radiochemistry , stereochemistry , organic chemistry , nuclear physics , physics
The deuterium / hydrogen NMR isotope effects on the 13 C chemical shift (DHIECS) of the cycloalkano[ b ]indoles 1,2,3,4‐tetrahydro‐9 H ‐carbazole, 3‐ tert ‐butyl‐1,2,3,4‐tetrahydro‐9 H ‐carbazole and 1,2,3,4‐tetrahydrocyclopent‐[ b ]indole, wherein the labile NH was partially exchanged to ND, were measured at a concentration of 0.83 M in CDCI 3 and in DMSO‐ d 6 solutions. The DHIECS values show defined trends that allow definitive 13 C NMR assignments. The isotope effects over three and four bonds for the sp 3 hybridized carbons are linearly interdependent, even when one of these isotope effects becomes negative.