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Isotopic effect on tautomeric behavior of 5‐(2,6‐disubstituted‐aryloxy)‐tetrazoles
Author(s) -
Noroozi Pesyan Nader
Publication year - 2011
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.2790
Subject(s) - chemistry , tautomer , isopropyl , tetrazole , ring (chemistry) , chemical shift , nmr spectra database , computational chemistry , proton nmr , spectral line , crystallography , medicinal chemistry , stereochemistry , organic chemistry , physics , astronomy
Isotopic effect on tautomeric behaviors of the synthesized 5‐phenoxy‐ (1a), 5‐(2,6‐dimethylphenoxy)‐ (1b), 5‐(2,6‐diisopropylphenoxy)‐ (1c), 5‐(2,6‐dimethoxyphenoxy)‐ (1d) and 5‐(4‐methylphenoxy)‐tetrazole (1e) were investigated in DMSO‐ d 6 by adding one drop of D 2 O. Among 1a–e, 1a, 1d and 1e show small rotational barrier around C5O1 and O1C6 while in 1b and 1c there are distinguishable rotational barrier about that bonds. The 1 H NMR spectra of 1b and 1c show slightly different chemical shifts for two methyl and isopropyl groups on those phenyl ring, respectively, while the chemical shifts difference (Δδ) between two methyl and two isopropyl groups were enhanced by adding D 2 O. The 13 C NMR spectra of 1b show two overlapped singlets for methyl groups after adding D 2 O. Representatively, the calculations of compound 1c were performed with GAUSSIAN‐03and the rotational barrier about C5O1 and between isopropyl group and phenyl ring in 1c was calculated with B3LYP/6‐31G(d) basis set. Copyright © 2011 John Wiley & Sons, Ltd.