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Karplus relationships of the 2 J HNα and 3 J ΗΝβ couplings in organic azides
Author(s) -
NavarroVázquez Armando,
Pennestri Matteo
Publication year - 2021
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.5101
Subject(s) - chemistry , geminal , azide , vicinal , dihedral angle , density functional theory , propagator , computational chemistry , natural bond orbital , crystallography , stereochemistry , hydrogen bond , mathematical physics , molecule , physics , organic chemistry
Density functional theory (DFT) and second‐order polarization propagator approximation (SOPPA) computations in model organic azides revealed a Karplus‐like dependence not only of the vicinal 3 J H–C–Nα–Nβ coupling but also of the geminal 2 J H–C–Nα one, with the H–C–N α N β dihedral angle. Karplus equations were derived from the DFT computations on the isopropylazide model system. In light of these stablished relationships, natural abundance 1 H– 15 N couplings obtained for the azide group of the zidovudine antiviral helped to probe its conformation around the C–N α bond as being of the synclinal type.