Adducts of Aryl Compounds of Antimony and Bismuth with Carboxylic Acids, Phenols, and Oximes

Reviews and Advances in Chemistry Pub Date : 2024-06-25 DOI:10.1134/s2634827624600117

O. K. Sharutina, V. V. Sharutin

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Abstract

During recrystallization from benzene or toluene of the products of interaction of triarylantimony or triarylbismuth with carboxylic acids, phenol, or oxime in the presence of tert-butyl hydroperoxide (molar ratio 1 : 2 : 1, diethyl ether, 24°C, 24 h), minor products, adducts of aryl compounds of antimony or bismuth of the Ar₃MX₂ type with carboxylic acids, phenol, and oxime are isolated. According to X-ray structural analysis conducted at 293 K using an automatic D8 Quest Bruker four-circle diffractometer (two-coordinate CCD detector, Mo K_α radiation, λ = 0.71073 Å, graphite monochromator), the metal atoms in the crystals of m-Tol₃Sb[OC(O)C₆H₃F₂-2,5]₂ ⋅ HOC(O)C₆H₃F₂-2,5 (1) [C₄₂H₃₁O₆F₆Sb, M 867.42; triclinic system, symmetry group P\(\bar {1}\); cell parameters a = 8.78(5) Å, b = 13.10(6) Å, c = 16.64(8) Å; α = 102.86(19)°, β = 99.3(2)°, γ = 98.0(3)°; V = 1813(16) Å³; Z 2; reflection index intervals –7 ≤ h ≤ 7, –11 ≤ k ≤ 11, –14 ≤ l ≤ 14; total reflections 14 149; independent reflections 2603; R_int 0.0284; GOOF 1.049; R₁ = 0.0348, wR₂ = 0.0938; residual electron density 0.55/–0.42 e/Å³], p‑Tol₃Bi[OC(O)C₆HF₄-3,4,5,6]₂ ⋅ HOC(O)C₆HF₄-3,4,5,6 (2) [C₄₂H₂₅O₆F₁₂Bi, M 1062.60; triclinic system, symmetry group P\(\bar {1}\); cell parameters a = 12.246(11) Å, b = 12.976(18) Å, c = 14.391(13) Å; α = 68.27(4)°, β = 69.89(3)°, γ = 86.11(5)°; V = 1990(4) Å³; Z 2; reflection index intervals –15 ≤ h ≤ 15, ‒16 ≤ k ≤ 16, –18 ≤ l ≤ 18; total reflections 48 542; independent reflections 9207; R_int 0.0321; GOOF 1.136; R₁ = 0.0322, wR₂ = 0.0648; residual electron density 1.81/–1.08 e/Å³], [(2-MeO-5-BrC₆H₃)₃SbOC₆H₄Br-4]₂O ⋅ 2HOC₆H₄Br-4 (3) [C₆₆H₅₄Br₁₀O₁₁Sb₂, M 2065.69; monoclinic system, symmetry group C2₁/c; cell parameters a = 12.017(14) Å, b = 25.54(3) Å, c = 13.181(18) Å; β = 116.71(5)°; V = 3613(8) Å³; Z 2; reflection index intervals –13 ≤ h ≤ 13, –27 ≤ k ≤ 27, –12 ≤ l ≤ 12; total reflections 29 461; independent reflections 4545; R_int 0.0656; GOOF 1.062; R₁ = 0.0565, wR₂ = 0.1200; residual electron density 1.59/–1.31 e/Å³], and [(2-MeO)C₆H₄]₃Sb[ON=CHC₄H₂(NO₂-2)]₂ ∙ 2HON=CHC₄H₂(NO₂-2) ∙ 1/2PhH (4) [C₄₄H₃₈N₈O₁₉Sb, M 1104.57; triclinic system, symmetry group P\(\bar {1}\); cell parameters a = 10.240(5) Å, b = 14.480(8) Å, c = 18.093(11) Å; α = 103.43(3)°, β = 104.50(2)°, γ = 98.876(17)°; V = 2461(2) Å³; Z 2; reflection index intervals –13 ≤ h ≤ 13, –18 ≤ k ≤ 18, –23 ≤ l ≤ 23; total reflections 58 643; independent reflections 10 886; R_int 0.0558; GOOF 1.061; R₁ = 0.0429, wR₂ = 0.1095; residual electron density 1.91/–0.51 e/Å³] show distorted trigonal-bipyramidal coordination with oxygen atoms in axial positions. Full tables of atom coordinates, bond lengths, and valence angles for the structures are deposited in the Cambridge Structural Database (no. 2050322 for 1, no. 2045173 for 2, no. 2070387 for 3, and no. 2119790 for 4; deposit@ccdc.cam.ac.uk; https://www.ccdc.cam.ac.uk).

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锑和铋的芳基化合物与羧酸、酚类和肟的加合物

摘要在叔丁基过氧化氢（摩尔比 1 : 2 : 1，二乙醚，24°C，24 小时）存在下，从苯或甲苯中重结晶三芳基锑或三芳基铋与羧酸、苯酚或肟作用的产物时，分离出了次要产物，即 Ar3MX2 型锑或铋芳基化合物与羧酸、苯酚和肟的加合物。根据在 293 K 温度下使用自动 D8 Quest Bruker 四圆衍射仪（双坐标 CCD 探测器，Mo Kα 辐射，λ = 0.71073 Å，石墨单色器）进行的 X 射线结构分析，m-Tol3Sb[OC(O)C6H3F2-2,5]2 ⋅ HOC(O)C6H3F2-2,5 (1) [C42H31O6F6Sb，M 867.42；三菱系，对称组 P\(\bar {1}\)；晶胞参数 a = 8.78(5)埃，b = 13.10(6)埃，c = 16.64(8)埃；α = 102.86(19)°，β = 99.3(2)°，γ = 98.0(3)°; V = 1813(16) Å3; Z 2; 反射指数区间 -7 ≤ h ≤ 7, -11 ≤ k ≤ 11, -14 ≤ l ≤ 14; 总反射 14 149; 独立反射 2603; Rint 0.0284；GOOF 1.049；R1 = 0.0348，wR2 = 0.0938；残余电子密度 0.55/-0.42 e/Å3]，p-Tol3Bi[OC(O)C6HF4-3,4,5,6]2⋅HOC(O)C6HF4-3,4,5,6 (2) [C42H25O6F12Bi，M 1062.60; triclinic system, symmetry group P\(\bar {1}\); cell parameters a = 12.246(11) Å, b = 12.976(18) Å, c = 14.391(13) Å; α = 68.27(4)°, β = 69.89(3)°, γ = 86.11(5)°; V = 1990(4) Å3; Z 2; 反射指数区间 -15 ≤ h ≤ 15, -16 ≤ k ≤ 16, -18 ≤ l ≤ 18; 总反射 48 542; 独立反射 9207; Rint 0.0321; GOOF 1.136; R1 = 0.0322, wR2 = 0.0648; 残余电子密度 1.81/-1.08 e/Å3], [(2-MeO-5-BrC6H3)3SbOC6H4Br-4]2O⋅2HOC6H4Br-4 (3) [C66H54Br10O11Sb2, M 2065.69；单斜晶系，对称基团 C21/c；晶胞参数 a = 12.017(14) Å, b = 25.54(3) Å, c = 13.181(18) Å; β = 116.71(5)°; V = 3613(8) Å3; Z 2; 反射指数区间 -13 ≤ h ≤ 13, -27 ≤ k ≤ 27, -12 ≤ l ≤ 12; 总反射 29 461; 独立反射 4545; Rint 0.0656; GOOF 1.062; R1 = 0.0565, wR2 = 0.1200; 残余电子密度 1.59/-1.31 e/Å3]，以及[(2-MeO)C6H4]3Sb[ON=CHC4H2(NO2-2)]2 ∙ 2HON=CHC4H2(NO2-2) ∙ 1/2PhH (4) [C44H38N8O19Sb, M 1104.57；三菱系，对称组 P\(\bar {1}\)；晶胞参数 a = 10.240(5)埃，b = 14.480(8)埃，c = 18.093(11)埃；α = 103.43(3)°，β = 104.50(2)°，γ = 98.876(17)°; V = 2461(2) Å3; Z 2; 反射指数区间 -13 ≤ h ≤ 13, -18 ≤ k ≤ 18, -23 ≤ l ≤ 23; 总反射 58 643; 独立反射 10 886; Rint 0.0558；GOOF 1.061；R1 = 0.0429，wR2 = 0.1095；残余电子密度 1.91/-0.51 e/Å3]显示了氧原子在轴向位置的扭曲三叉双锥配位。这些结构的原子坐标、键长和价角的完整表格已存入剑桥结构数据库（1 的编号为 2050322，2 的编号为 2045173，3 的编号为 2070387，4 的编号为 2119790；deposit@ccdc.cam.ac.uk；https://www.ccdc.cam.ac.uk）。

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