A “sodium trap” based on benzo-15-crown-5 with an exocyclic N-(thiophosphoryl)thiourea moiety

For N-(thio)phosphorylthioureas of the common formula RC(S)NHP(X)(OiPr)2HLI (R = N-(4′-aminobenzo-15-crown-5), X = S), HLII (R = N-(4′-aminobenzo-15-crown-5), X = O), HLIII (R = PhNH, X = S), HLIV (R = PhNH, X = O), and (N,N′-bis-[C(S)NHP(S)(OiPr)2]2-1,10-diaza-18-crown-6) H2LV, salts LiLI,III,IV, NaLI–IV, KLI–IVM2LV (M = Li+, Na+, K+), Ba(LI,III,IV)2, and BaLV have been synthesized and investigated. Compounds NaLI,II quantitatively drop out as a deposit in ethanol medium, allowing the separation of Na+ and K+ cations. This effect is not displayed for the other compounds. The crystal structures of HLIII and the solvate of the composition [K(Me2CO)LIII] have been investigated by X-ray crystallography.

Graphical abstractFor N-(thio)phosphorylthioureas of the common formula RC(S)NHP(X)(OiPr)2HLI, HLII, HLIII, HLIV, and (N,N′-bis-[C(S)NHP(S)(OiPr)2]2-1,10-diaza-18-crown-6) H2LV, salts LiLI,III,IV, NaLI–IV, KLI–IVM2LV (M = Li+, Na+, K+), Ba(LI,III,IV)2 and BaLV have been synthesized and investigated. Compounds NaLI,II quantitatively drop out as a deposit in ethanol medium, allowing the separation of Na+ and K+ cations. This effect is not displayed for the other compounds. The crystal structure of HLIII and the solvate of the composition [K(Me2CO)LIII] have been investigated by X-ray crystallography.Figure optionsDownload full-size imageDownload as PowerPoint slide