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13 C and 15 N NMR spectra of high‐energy polyazidocyanopyridines
Author(s) -
Chapyshev Sergei V.,
Chernyak Alexander V.,
Ushakov Evgeny N.
Publication year - 2017
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.4495
Subject(s) - chemistry , chemical shift , polarizable continuum model , density functional theory , basis set , spectral line , nmr spectra database , molecule , computational chemistry , solvent effects , carbon 13 nmr , polarizability , crystallography , solvent , stereochemistry , organic chemistry , physics , astronomy
13 C and 15 N NMR spectra of high‐energy 2,4,6‐triazidopyridine‐3,5‐dicarbonitrile, 2,3,5,6‐tetraazidopyridine‐4‐carbonitrile and 3,4,5,6‐tetraazidopyridine‐2‐carbonitrile are reported. The assignment of signals in the spectra was performed on the basis of density functional theory calculations. The molecular geometries were optimized using the M06‐2X functional with the 6‐311+G(d,p) basis set. The magnetic shielding tensors were calculated by the gauge‐independent atomic orbital method with the Tao–Perdew–Staroverov–Scuseria hybrid functional known as TPSSh. In all the calculations, a polarizable continuum model was used to simulate solvent effects. This approach provided accurate predictions of the 13 C and 15 N chemical shifts for all the three compounds despite complications arising due to non‐coplanar arrangement of the azido groups in the molecules. It was found that the 15 N chemical shifts of the N α atoms in the azido groups of 2,4,6‐triazidopyridines correlate with the 13 C chemical shifts of the carbon atoms attached to these azido groups. Copyright © 2016 John Wiley & Sons, Ltd.