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Hindered rotation around the N(sp2)-C(sp3) single bond in 2,4,6-trimethyl-N-alkylpyridinium cations:H DNMR analysist

✍ Scribed by Alexandru T. Balaban; Cornelia Uncuţ/a; Mihai Elian; Filip Chiraleu; Antonie Dinculescu

Book ID: 104203068
Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 610 KB
Volume: 40
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)83508-0

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✦ Synopsis

Abstnct--Painvise chemical shift nonequivalence of the Z&methyl and 3,5-protons in 'H NMR spectra, as well as of the 2,6-methyl, 2,6-ring and 3,5-ring carbons in lrCNNMR spectra, was observed for N-alkyl-2,4,6-trimethylpyridinium salts 2. Dynamic NMR spectroscopy demonstrates appreciably higher activation free energies AG + for rotation around the N(spp-C(sp3) bond than AG + for the analogously substituted mesityl derivatives, in agreement with the shorter N-C bond distance than for the C-C bond.

Me Cl+OR

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