Infrared spectra and protonation of 1,8-bis(dimethylamino)naphthalene in acetonitrile
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Faraday Transactions
- Vol. 86 (10) , 1777-1780
- https://doi.org/10.1039/ft9908601777
Abstract
Fourier-transform infrared studies on 1,8-bis(dimethylamino)naphthalene (DMAN) salts in acetonitrile have been performed. In contrast to solid salts very broad ‘continua’ of protonic absorption are observed typical of the usual NHN+ homoconjugated cations formed by the hydrogen bases. The deuterium isotopic ratio ν(NHN)/ν(NDN), estimated from the positions of the band weighted centres, is equal to ca. 1. For some salts a deprotonization of DMANH+ and formation of homoconjugated anions were detected. The tendency to form the homoconjugated anions can be arranged in the sequence C6ClO– 5 > NO– 3 > NCS– > Cl– > ClO– 4. in the case of pentachlorophenolate free DMAN, protonated DMAN and homoconjugated anions are present in the solution in the proportion 1 : 1 : 1.Keywords
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