Tris(2-hydroxyethyl)ammonium salts: 2,8,9-Trihydroprotatranes

Abstract

New method of synthesis of tris(2-hydroxyethyl)ammonium salts, 2,8,9-trihydroprotatranes X-[HN(CH2CH2OH)3]+, based on the reaction of tris(2-hydroxyethyl)amine (triethanolamine) with ammonium salts NH4X (X = F, Cl, Br, I, NO3, ClO4) was developed. 1H, 13C, 15N NMR and IR spectra of these protatranes were investigated, as well as those of their analogs with X = RCH2COO (R = H; 2-MeC6H4O; 2-Me-4ClC6H3O; 2-MeC6H4S; 4-ClC6H4S; 4-ClC6H4SO2; 3-IndS; 3-(PhCH2-IndS) prepared from the corresponding acids RCH2COOH and triethanolamine. The parameters of IR and NMR spectra of the studied protatranes were governed by the nature of substituent X, which also determined the character of the intra and intermolecular hydrogen bonds NH⋯O and OH⋯O in the protatrane framework.