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Characterization of dinitrobenzimidazoles using NOE difference and heterocorrelated NMR
Author(s) -
Freyer Alan J.,
Nissan Robin A.,
Wilson William S.
Publication year - 1993
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.1260310104
Subject(s) - chemistry , nuclear overhauser effect , two dimensional nuclear magnetic resonance spectroscopy , nuclear magnetic resonance spectroscopy , chemical shift , proton nmr , nmr spectra database , fluorine 19 nmr , nitro , stereochemistry , spectral line , organic chemistry , physics , alkyl , astronomy
Abstract Several 1‐(2′,4′,6′‐trinitrophenyl)dinitrobenzimidazoles (1‐picryldinitrobenzimidazoles) were synthesized as part of an ongoing study of heterocyclic nitro compounds as energetic materials and their structure–property relationships. The 1‐picryl‐4,6‐dinitrobenzimidazoles and their 1‐methyl analogs were examined by several NMR techniques in order to confirm their structures, and assignment strategies are discussed. Nuclear Overhauser enhancement (NOE) difference spectroscopy and 1 H/ 13 C correlation experiments were used to make definitive assignments of the 1 H and 13 C NMR spectra. It was found that both solvent and temperature had significant effects on the chemical shifts of the benzimidazole protons. This was especially true for the 1‐picryl derivatives.