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)(2) HLI (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-IV M2LV (M = Li+, Na+, K+), Ba(L-I,L-III,L-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)L-III] have been investigated by X-ray crystallography. (C) 2006 Elsevier Ltd. All rights reserved.