Synthesis and structure of organyltriphenylphosphonium organosulfonates [Ph3PR][OSO2R’], R = Ph, R’ = C6H3Cl2-2,5; R = C6H11-cyclo, R’ = C6H3Cl2-2,5; R = CH2OMe, R’ = C6H3(NO2)2-2,4; R = CH2OMe, R’ = C6H4(COOH-2).
Keywords:
organyltriphenylphosphonium organosulfonate, synthesis, structure, X-ray diffraction analysisAbstract
The interaction of equimolar amounts of tetraorganylphosphonium chloride with 2,5-dichlorobenzenesulfonic, 2,4-dinitrobenzenesulfonic, and 2-carboxybenzenesulfonic acids in water leads to the formation of organyltriphenylphosphonium organosulfonates [Ph3PR][OSO2R’], R = Ph, R’ = C6H3Cl2-2,5 (1); R = C6H11-cyclo, R’ = C6H3Cl2-2,5 (2); R = CH2OMe, R’ = C6H3(NO2)2-2,4 (3); R = CH2OMe, R’ = C6H4(COOH-2) (4). Structures of complexes 1‒4 have been established by X-ray diffraction analysis, carried out on an automatic four-circle D8 Quest Bruker diffractometer (CCD detector, МоКα-radiation, λ = 0.71073 Å, graphite monochromator) at 293 K. Crystals 1 [C30H27Cl2O5PS, M 601.45; triclinic syngony, space group P-1; сell parameters: a = 10.998(5), b = 11.358(6), c = 12.923(10) Å; = 85.54(3), β = 67.47(2), = 76.81(2) deg., V = 1451.5(15) Å3, Z = 2; calc = 1.376 g/cm3; m = 0.389 mm–1; F(000) = 624.0; Rint = 0.0393, GOOF = 1.034], 2 [C30H29Cl2O3PS, M 571.46; monoclinic syngony, space group Cc; сell parameters: a = 9.089(4), b = 17.082(7), c = 17.647(7) Å; = 90.00, β = 97.22(2), = 90.00 deg., V = 2718.0(19) Å3, Z = 4; calc = 1.397 g/cm3; m = 0.406 mm–1; F(000) = 1192.0; Rint = 0.0241, GOOF = 1.037], 3 [C26H23N2O8PS, M 554.49; triclinic syngony, space group P-1; сell parameters: a = 9.437(6), b = 11.424(10), c = 13.685(12) Å; = 65.34(3), β = 84.66(3), = 72.68(3) deg., V = 1279.3(17) Å3, Z = 2; calc = 1.439 g/cm3; m = 0.243 mm–1; F(000) = 576.0; Rint = 0.0395, GOOF = 1.033], and 4 [C27H25O6PS, M 508.50; triclinic syngony, space group P-1; сell parameters: a = 8.263(11), b = 12.085(17), c = 12.987(14) Å; = 84.17(5), β = 86.78(4), = 83.51(6) deg., V = 1281(3) Å3, Z = 2; calc = 1.319 g/cm3; m = 0.229 mm–1; F(000) = 532.0; Rint = 0.0423, GOOF = 1.024]. The coordination of phosphorus atoms in cations 1‒4 is tetrahedral; organosulfonate anions have the usual geometry with a tetrahe-dral sulfur atom. The values of the Р−С bond lengths are 1.7665(18)1.836(2) Å, which is less than the sum of the covalent radii of the partner atoms (1.88 Å). The СРС valence angles vary in range of values 103.81(6)113.43(7) deg. The structural organization in crystals 1‒4 is due to weak hydrogen bonds between cations and anions, for example, S=O•••HCAr, N=O•••HCAr, C=O•••HCAr, etc. The arenesulfonate anions in complex 1 are structured into dimers by means of the crystallization water molecules. Complete tables of atomic coordinates, bond lengths and bond angles for structures have been deposited at the Cambridge Crystallographic Data Centre (No. 2142598 (1), No. 2144330 (2), No. 2144708 (3), No. 2145604 (4); deposit@ccdc.cam.ac.uk; https://www.ccdc.cam.ac.uk).References
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