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NMR studies on σ‐adducts of heterocyclic systems with nucleophiles . VI —Carbon‐13 nuclear magnetic resonance investigations on σ‐adduct formation of pyrimidine and some of its derivatives with potassium amide in liquid ammonia
Author(s) -
Geerts J. P.,
van der Plas H. C.,
van Veldhuizen A.
Publication year - 1975
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270070208
Subject(s) - adduct , chemistry , amide , pyrimidine , nucleophile , nmr spectra database , liquid ammonia , medicinal chemistry , carbon 13 nmr , ammonia , stereochemistry , organic chemistry , spectral line , catalysis , physics , astronomy
Carbon‐13 NMR spectra of the σ‐adduct complexes formed in liquid ammonia between the amide ion and some 2‐R‐pyrimidines, some 4‐chloro‐2‐R‐pyrimidines (R = dimethylamino‐, N ‐methylanilino, piperidino‐, morpholino‐, phenyl‐), 5‐bromo‐2‐piperidinopyrimidine and pyrimidine itself are described, together with the carbon‐13 NMR spectra of the anions formed by amino‐proton abstraction resulting from the reaction of the amide ion with 2‐anilino‐4‐chloro‐, 4‐chloro‐2‐methylamino‐, 2‐anilino‐ and 2‐methylaminopyrimidine in liquid ammonia. Additionally, the carbon‐13 NMR spectra of the parent compounds of the anionic σ‐adducts and anions, and that of 4‐chloropyrimidine, were recorded in CDCl 3 .