Abstract
The reaction of the pentaphenyphosphorus solvate Ph5P·1/2PhH (I) with carboxylic and sulfonic acids was used to synthesize tetraphenylphosphonium carboxylates Ph4POC(O)R, R = C6H4(2-OH) (II), C6H4 (2-COOH) (III), H (IV), Me (V), CCl3 (VI), Ph (VII), PhCH=CH (VIII), CH2CH2C(O)OH (IX), CH=CHC(O) OH(X), and CH2C(O)OH (XI) and tetraphenylphosphonium sulfonates Ph4POSO2Ar, Ar = Ph (XII), C6H4Me4 (XIII), and C6H3(-COOH)(4-OH) (XIV). Compound XII was also prepared from compound I and SO3 in benzene. According to X-ray diffraction data, the crystals of I contain two types of crystallographically independent molecules with a slightly distorted trigonal-bipyramidal configuration [Ia, CaxPCax 178.44(8)°, P- Cax 1.985(2), 1.987(2) Å, P-Ceq 1.854(2), 1.846(2), 1.840(2) Å; Ib, CaxPCax 178.45(9)°, P-Cax 1.980(2), 1.975 (2) Å, P-Ceq 1.840(2), 1.846(2), 1.854(2) Å]. In the cations of compounds II, III and XIV, the coordination of the phosphorus atom is tetrahedral [CPC angle: II, 106.2(2)−111.6(1)°; III, 104.01(6)−113.03(6)°; XIV, 107.54 (6)−112.79(6)°]; the anions contain intramolecular O-H⋯O hydrogen bonds between the hydroxyl hydrogen atom and carboxyl oxygen atom (II, 1.34; III, 1.23; and XIV, 1.83 Å).
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Original Russian Text © V.V. Shaturin, V.S. Senchurin, O.K. Shaturina, E.A. Boyarkina, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 1, pp. 80–89.
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Shaturin, V.V., Senchurin, V.S., Shaturina, O.K. et al. Tetraphenylphosphonium carboxylates and sulfonates. Synthesis and structure. Russ J Gen Chem 79, 78–87 (2009). https://doi.org/10.1134/S1070363209010125
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DOI: https://doi.org/10.1134/S1070363209010125