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1H NMR studies on intramolecular hydrogen bonding in perchlorates of N-(pyridyl)amides of 6-methylpicolinic acid N-oxide

✍ Scribed by Bogumil Brzezinski

Publisher
John Wiley and Sons
Year
1979
Tongue
English
Weight
347 KB
Volume
12
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^1^H NMR spectra of perchlorates of N‐(pyridyl)amides of 6‐methylpicolinic acid N‐oxide (PYAP) in CD~3~CN at 100 MHz show two proton signals belonging to two distinct intramolecular hydrogen bonds. The position of these signals is independent of concentration and temperature. That of the proton of the NH ⃛O bond in PYAP is shifted to still lower field than in N‐(pyridyl)amides of 6‐methylpicolinic acid N‐oxide (PYA) due to the inductive effect of the pyridine cation and the formation of another intramolecular hydrogen N^+^H ⃛O bond. The proton of the N^+^H ⃛O bond interacts strongly with its environment and is highly sensitive to traces of water. Presumably, water leads to dissociation of the intramolecular bond.

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