Preparation of pseudo-arsonolipids: 2-acyloxypropane-1,3-bis(arsonic acids). The crystal structure of 2-hydroxypropane-1,3-bis(arsonic acid).
Epihalohydrins react with alkaline arsenite to give in very good yields 2-hydroxypropane-1,3-bis(arsonic acid) (7), a key compound for the synthesis of pseudo-arsonolipids and more complex arsinolipids. Through a series of reduction to -As(SPh)(2), acylation, and oxidation to -AsO(3)H(2), pseudo-arsonolipids, i.e. 2-acyloxypropane-1,3-bis(arsonic acids), were obtained. These pseudo-lipids are very sensitive to bases, being de-acylated. The bis(arsonic acid) (7) crystallizes in the orthorombic space group P2(1)2(1)2(1) with unit cell constants a=6.911(3), b=17.496(8), c=7.002(3) A. Both arsenic atoms are essentially tetrahedral being bound to three oxygens and one carbon. All hydrogen atoms have been located. There is no intramolecular but only intermolecular hydrogen bonding involving all the As=O, As-OH, and C-OH groups. The C-OH group acts as a hydrogen donor to an acidic As-OH, and this As-OH, in turn, acts as a hydrogen donor to an As=O group.
Terzis
Aris
A
Institute of Material Science, NCSR Democritos, 15310 Aghia Paraskevi Attikis, Greece. ioannou@chemistry.upatras.gr
Ioannou
Panayiotis V
PV
D001152:Arsenicals / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D001152:Arsenicals; D008055:Lipids; C054806:arsonic acid