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1H and 13C NMR studies of 1,8-bis(dimethylamino)naphthalene salts in acetonitrile-d3

✍ Scribed by Bogumil Brycki; Bogumil Brzeziński; Eugeniusz Grech; Zbigniew Malarski; Lucjan Sobczyk

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
285 KB
Volume
29
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^1^H and ^13^C NMR spectra were studied for a number of 1,8‐bis(dimethylamino)naphthalene (DMAN) salts in acetonitrile‐d~3~. In the case of strong acids no counter anion effect was observed on the protonated DMAN molecules. A splitting of the ^1^H signal of the CH~3~ groups was found which was caused by coupling with the bridge NHN^+^ proton. It was confirmed that the salt with pentachlorophenol (PCP) undergoes a transformation to a nearly equimolar solution of free DMAN, protonated DMAN and the homoconjugated anion of PCP. The formation of the NHN^+^ bridge with an equally shared proton between the two nitrogen atoms leads to a change in the charge distribution in the naphthalene ring which is analogous to, but much weaker than, that found on protonation of aniline.

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