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Observation of Diastereotopic Signals in 15 N NMR Spectroscopy
Author(s) -
Alkorta Ibon,
Dardonville Christophe,
Elguero José
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201412144
Subject(s) - chirality (physics) , nuclear magnetic resonance spectroscopy , chemistry , spectroscopy , coupling constant , carbon 13 nmr satellite , chemical shift , benzimidazole , transverse relaxation optimized spectroscopy , computational chemistry , crystallography , fluorine 19 nmr , stereochemistry , organic chemistry , chiral symmetry , physics , particle physics , quantum mechanics , nambu–jona lasinio model , quark
The first example in the literature of a compound showing anisochronous 15 N atoms resulting from diastereotopicity is described. Racemic 1,3‐dimethyl‐2‐phenyloctahydro‐1 H ‐benzimidazole was prepared and studied by 1 H, 13 C and 15 N NMR spectroscopy. If convenient conditions were used (monitored by theoretical calculations of 2 J N‐H spin–spin coupling constants), two 15 N NMR signals were observed and corresponded to the diastereotopic atoms. GIAO/density‐functional calculations of chemical shifts were not only in good agreement with the experimental values but also served as prediction tools. This study suggests that 15 N NMR spectroscopy could be used to probe chirality.