Complexes of TETROL with selected heterocyclics: unconventional host–guest hydrogen bonding and the correlation with host selectivity

Host Ability of (+)-(2R,3R)-1,1,4,4-Tetraphenylbutane-1,2,3,4-tetraol (TETROL) in the Presence of γ-Butyrolactone-, 2-Pyrrolidone-, and N-Alkyl-substituted 2-Pyrrolidones

“…This tartaric acid-derived compound displayed selectivity when crystallized from mixed pyridines, 14 cyclohexanones, 15−17 alkyl aromatics and anilines (both C-and N-alkylated), 18−20 and both saturated and unsaturated sixmembered heterocyclic compounds. 21 In the present work, we have considered the behavior of TETROL as a host compound in the presence of potential guests γ-butyrolactone (GBL), 2pyrrolidone (NP), N-methyl-2-pyrrolidone (NMP), and Nethyl-2-pyrrolidone (NEP) (Scheme 1), which are important organic solvents and also find application in both drug actives and drug formulations. In fact, GBL (bp 204 °C) is often used as a starting material for the preparation of both NMP (bp 202 °C) and NEP (bp 212 °C) by converting the cyclic ester functional group to the cyclic amide by treatment with methylamine or ethylamine, respectively (Scheme 1).…”

“…(+)-(2 R ,3 R )-1,1,4,4-Tetraphenylbutane-1,2,3,4-tetraol (TETROL, Scheme ), a host compound that only possesses temporary interstitial cavities in the presence of the guest compound and only in the solid state (hence known as a clathrand , with its complexes termed as clathrates ) has demonstrated rich host–guest chemistry in ongoing investigations in our laboratory. This tartaric acid-derived compound displayed selectivity when crystallized from mixed pyridines, cyclohexanones, − alkyl aromatics and anilines (both C - and N -alkylated), − and both saturated and unsaturated six-membered heterocyclic compounds . In the present work, we have considered the behavior of TETROL as a host compound in the presence of potential guests γ-butyrolactone (GBL), 2-pyrrolidone (NP), N -methyl-2-pyrrolidone (NMP), and N -ethyl-2-pyrrolidone (NEP) (Scheme ), which are important organic solvents and also find application in both drug actives and drug formulations.…”