TY - JOUR
T1 - Strong hydrogen bond-mediated complexation of H2PO4- by neutral bis-thiourea hosts
AU - Bühlmann, Philippe
AU - Nishizawa, Seiichi
AU - Xiao, Kang Ping
AU - Umezawa, Yoshio
N1 - Funding Information:
We are indebted to Dr. M. Sasaki for assistancei n mass spectroscopy and S. Amemiya for various interestingd iscussions. This work was supportedb y the Ministry of Education, Science and Culture, Japan, the TokuyamaS cienceF oundationa nd a SasakawaS cientific ResearchG rant from the Japan Science Society.
PY - 1997/2/3
Y1 - 1997/2/3
N2 - Highly preorganized bis-thiourea receptors based on a xanthene spacer selectively (H2PO4- > CH3COO- > Cl-) bind dihydrogenphosphate via multitopic hydrogen bonding, giving stronger complexes with H2PO4- than any synthetic neutral receptor known so far. The high complexation strengths are rationalized by the hydrogen bond donor strength of the thiourea groups and by host preorganization. The hydrogen bond acceptor strengths of the guest anions and, for small ions, guest solvation explain the observed selectivity of complexation in dimethyl sulfoxide (DMSO).
AB - Highly preorganized bis-thiourea receptors based on a xanthene spacer selectively (H2PO4- > CH3COO- > Cl-) bind dihydrogenphosphate via multitopic hydrogen bonding, giving stronger complexes with H2PO4- than any synthetic neutral receptor known so far. The high complexation strengths are rationalized by the hydrogen bond donor strength of the thiourea groups and by host preorganization. The hydrogen bond acceptor strengths of the guest anions and, for small ions, guest solvation explain the observed selectivity of complexation in dimethyl sulfoxide (DMSO).
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U2 - 10.1016/S0040-4020(96)01094-0
DO - 10.1016/S0040-4020(96)01094-0
M3 - Article
AN - SCOPUS:0031550583
SN - 0040-4020
VL - 53
SP - 1647
EP - 1654
JO - Tetrahedron
JF - Tetrahedron
IS - 5
ER -