Synthesis and structure of alkyltriphenylphosphonium arenesulfonates [Ph3PEt][OSO2С6H4(СOOH-2)], [Ph3PС3H5-cyclo][OSO2Naf-1], [Ph3PСH2СN][OSO2С6H2(Me3-2,4,6], [Ph3PCH2C≡CH][OSO2C6H4(COOH-2)], [Ph3PCH2OH][OSO2C6H3(OH- 4)(COOH-3)], [Ph3PCH2OH] [OSO2С6H3(Cl2-2,5] ∙ H2O

Abstract

Alkyltriphenylphosphonium arenesulfonates [Ph3PEt][OSO2С6H4(СOOH-2)] (1), [Ph3PС3H5-cyclo][OSO2Naf-1] (2), [Ph3PСH2СN][OSO2С6H2(Me3-2,4,6] (3), [Ph3PCH2C≡CH][OSO2C6H4(COOH-2)] (4), [Ph3PCH2OH][OSO2C6H3(OH-4)(COOH-3)] (5), [Ph3PCH2OH] [OSO2С6H3(Cl2-2,5] ∙ H2O (6) were obtained by substitution reaction from tetraorganylphosphonium halides and arenesulfonic acids in water, yielding up to 90%. The structure of complexes 1–6 was proven by IR spectroscopy and X-ray diffraction analysis. According to the X-ray diffraction data, crystals of the complexes have ionic structure and consist of tetraorganylphosphonium cations and arenesulfonate anions. Crystals (1) [Ph3PEt][OSO2С6H4(СOOH-2)], C27H25O5PS, M 492.50; triclinic syngony, symmetry group P–1; cell parameters: a = 8.645(6), b = 11.385(6), c = 13.194(7) Å;  = 74.954(17), β = 73.72(3),  = 89.24, V = 1201.3(12) Å3; Z = 2; calc = 1.362 g/cm3; 2: 5.9665.22 deg.; total reflections 63751; independent reflections 8716; number of refined parameters 309: Rint = 0.0466; GOOF 1.091; R1 = 0.0500, wR2 = 0.1129; residual electron density (max/min): 0.23/0.45 e/Å3], (2) [Ph3PС3H5-cyclo][OSO2Naf-1], C62H54O6P2S2, M 1021.11; orthorhombic syngony, symmetry group P-ca21; cell parameters: a = 18.215(11), b = 21.189(12), c = 13.330(8) Å;  = β =  = 90.00; V = 5145(5) Å3, Z = 4; calc = 1.318 g/cm3; 2: 5.7456.66 deg.; total reflections 94209; independent reflections 12754; number of refined parameters 649: Rint = 0.01669; GOOF 1.016; R1 = 0.0759, wR2 = 0.1639; residual electron density (max/min): 0.72/0.35 e/Å3], (3) [Ph3PСH2СN][OSO2С6H2(Me3-2,4,6], C29H28NO3PS, M 501.55; monoclinic syngony, symmetry group P21/c; cell parameters: a = 13.033(18), b = 14.544(12), c = 13.941(13) Å; β = 101.30(4) deg., V = 2591(5) Å3, Z = 4; calc = 1.286 g/cm3: 2: 5.5458.88 deg.; total reflections 109265; independent reflections 7027; number 319 parameters to be refined; Rint = 0.0444; GOOF 1.051; R1 = 0.0408, wR2 = 0.1047; residual electron density (max/min): 0.22/0.51 e/Å3], (4) [Ph3PCH2C≡CH][OSO2C6H4(COOH-2)], C28H23O5PS, M 502.49; triclinic syngony, symmetry group P–1; cell parameters: a = 8.065(5), b = 12.708(6), c = 12.844(6) Å;  = 100.120(19), β = 91.87(3),  = 99.88(2), V = 1274.0(12) Å3; Z = 2; calc = 1.310 g/cm3; 2: 5.8857 deg.; total reflections 72756; independent reflections 6448; number of refined parameters 332; Rint = 0.0369; GOOF 1.044; R1 = 0.0393, wR2 = 0.0991; residual electron density (max/min); 0.27/0.37 e/Å3], (5) [Ph3PCH2OH][OSO2C6H3(OH-4)(COOH-3)], C27H22NO6PS, M 519.49; triclinic syngony, symmetry group P–1; cell parameters: a = 8.578(4), b = 12.727(8), c = 12.854(5) Å;  = 64.259(19), β = 83.41(2),  = 88.26(3), V = 1255,3(12) Å3; Z = 2; calc = 1.374 g/cm3; 2: 5.6270.34 deg.; total reflections 84712; independent reflections 11044; number of refined parameters 335; Rint = 0.0413; GOOF 1.020; R1 = 0.0518, wR2 = 0.1269; residual electron density (max/min); 0.75/0.45 e/Å3]; (6) [Ph3PCH2OH][OSO2С6H3(Cl2-2,5]∙H2O, C50H44Cl4O9P2S2, M 1056.71; monoclinic syngony, symmetry group P21/n; cell parameters: a = 9.120(5), b = 12.936(8), c = 21.094(13) Å; β = 90.32(2), V = 2489(3) Å3; Z = 4; calc = 1.410 g/cm3; 2: 5.7857 deg.; total reflections 56284; independent reflections 6307; number of refined parameters 323; Rint = 0.0503; GOOF 1.034; R1 = 0.0476, wR2 = 0.1156; residual electron density (max/min): 0.51/0.47 e/Å3].