ISSN:
0749-1581
Keywords:
1H
;
NMR
;
13C
;
NMR
;
1,8-Bis(dimethylamino)naphthalene
;
salts
;
Intramolecular
;
NHN+
;
hydrogen bond
;
Homoconjugated anions
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1H and 13C NMR spectra were studied for a number of 1,8-bis(dimethylamino)naphthalene (DMAN) salts in acetonitrile-d3. In the case of strong acids no counter anion effect was observed on the protonated DMAN molecules. A splitting of the 1H signal of the CH3 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.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260290603
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