Synthesis of Triphenylantimony Bis(2-Hydroxypropanoate) Ph3Sb(O2CCH(OH)CH3)2

Abstract

Triphenylantimony bis(2-hydroxypropanoate) Ph₃Sb(O₂CCH(OH)CH₃)₂ was obtained by the oxidative addition reaction of triphenylantimony and 2-hydroxypropenoic acid in the presence of hydrogen peroxide in isopropyl alcohol at room temperature. The product was purified by recrystallization from a hexane-chloroform (4:1) mixture and confirmed by elemental analysis, IR, ¹H and ¹³C-NMR spectroscopy. The yield of the purified material was 55 %, m.p. 50 ºС. The ¹H NMR spectrum (CDCl3, δ, ppm) contained ortho-proton signals of 7.82 (d, J = 71.5 Hz, 6H), meta- and para-protons of 7.60-7.43 (m, 9H) of phenyl groups, protons of methyne and hydroxyl groups 4.26 (dd, J = 31.6, 5.9 Hz, 4H), protons of methyl groups 1.43 (s, 6H). The ¹³C NMR spectrum (CDCl3, δs, ppm) contained the signals: 178.60 (COO-), 135.35 (Sb–C), 131.91 (o-Ph), 129.60 (m-, p-Ph), 66.74 (CH), 20.24 (CH3). In the IR spectrum there were signals (cm^–1): 447–459 ν(Sb–C), 693 ν(Sb–O), 734–747 ν(C–O), 1102–1127 δ(CH), 1567–1600 νas(COO), 1306–1384 νs(COO), 2890 ν(CH, CHOH), 2930–2981 ν(CH, CH3), 3055–3069 ν(CH, Ph), 3400–3500 ν(OH). The elemental analysis data were in good agreement with the calculated values. Found, %: C 54.37, H 4.81. C₂₄H₂₅O₆Sb. Calculated, %: C 54.2, H 4.71