P. Milart et K. Stadnicka, Salts of 4-(2,4,6-triphenyl-1-pyridinio)phenolate with p-toluenesulfonic acid in molar ratio 1 : 1 and 2 : 1 - Crystal and molecular structure, EUR J ORG C, (12), 2001, pp. 2337-2341
Two new salts of 4-(2,4,6-Triphenyl-1-pyridinio)phenolate with p-toluenesul
fonic acid in molar ratio 2:1 ("red salt") and 1:1 ("colourless salt") were
synthesised. The solvatochromic effect, H-1 NMR spectra and crystal struct
ure of the salts were investigated. In the crystalline "red salt" two molec
ules of the betaine dye are joined by a strong, asymmetric hydrogen bond co
ntrary to previous suggestions. Similar behaviour is observed in polar solv
ents, but the hydrogen bond is symmetric. In solvents of low polarity an ad
ditional intermolecular charge-transfer interaction is possible.