Crystal Structures of Alkyl(triphenyl)phosphonium 2,4-Dinitrobenzenesulphonates [PH3PAlk][X], X = OSO2C6H3(NO2)2-2,4; Alk = cyclo-C3H5, (CH2)2OH, CH2OH, CH2C(O)Me

被引:0
作者
Sharutin, V. V. [1 ]
Mekhanoshina, E. S. [1 ]
机构
[1] South Ural State Univ, Chelyabinsk 454080, Russia
关键词
2,4-dinitrobenzenesulfonic acid; alkyltriphenylphosphonium bromide; alkyltriphenylphosphonium 2,4-dinitrobenzenesulfonate; synthesis; molecular structure; X-ray diffraction analysis;
D O I
10.1134/S0012500825600099
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reactions of alkyltriphenylphosphonium bromides with 2,4-dinitrobenzenesulfonic acid in water lead to the formation of ionic alkyltriphenylphosphonium 2,4-dinitrobenzenesulfonates [Ph(3)PAlk][OSO2C6H3(NO2)(2)-2,4] (Alk = cyclo-C3H5 (1), (CH2)(2)OH (2), CH2OH (3), and CH2C(O)Me (4). Crystals of 1 (C27H23N2O7PS, FW 550.50; monoclinic system, space group P-1; unit cell parameters: a = 9.354(11) angstrom, b = 9.764(10) angstrom, c = 15.416(17) angstrom; alpha = 106.29(4)degrees, beta = 94.67(5)degrees, gamma = 97.98)6)degrees, V = 1328(3) angstrom 3, Z = 2; rho X = 1.377 g/cm(3)), 2 (C26H23N2O8PS, FW 554.49; monoclinic system, space group P2(1)/c; unit cell parameters: a = 13.049(7) angstrom, b = 14.816(10) angstrom, c = 13.261(7) angstrom; alpha = 90.00 degrees, beta = 93.901(15)degrees, gamma = 90.00 degrees, V = 2558(2) angstrom 3, Z = 4; rho X = 1.440 g/cm(3)), 3 (C25H21N2O8PS, M 540.47; triclinic system, space group P-1; unit cell parameters: a = 9.086(14) angstrom, b = 10.95(2) angstrom, c = 13.17(2) angstrom; alpha = 86.20(9)degrees, beta = 71.93(6)degrees, gamma = 89.51(11)degrees, V = 1243(4) angstrom 3, Z = 2; rho X = 1.444 g/cm(3)), and 4 (C27H23N2O8PS, FW 566.50; triclinic system, space group P-1; unit cell parameters: a = 9.746(10) angstrom, b = 11.371(11) angstrom, c = 13.657(10) angstrom; alpha = 66.78(3)degrees, beta = 86.30(3)degrees, gamma = 74.46(5)degrees, V = 1339(2) angstrom 3, Z = 2; rho X = 1.405 g/cm(3)). According to X-ray diffraction data, the phosphorus atoms in cations 1-4 have a distorted tetrahedral coordination, while the sulfonate anions have a normal geometry with a tetrahedral sulfur atom. The P-C bond lengths vary in the range 1.768(3)-1.830(3) angstrom; the CPC bond angles are within 105.54(9)degrees-112.42(9)degrees. In the arenesulfonate anions of the complexes, the S-C distances are close to each other (1.794(2)-1.807(3) angstrom), and the S-O bond lengths are similar (1.363(4)-1.495(4) angstrom). The structural organization in complexes 1-4 is mainly due to weak intermolecular contacts of the O center dot center dot center dot H type 2.31-2.71 angstrom (1), 2.35-2.64 angstrom (2), 2.38-2.70 angstrom (3), and 2.24-2.90 angstrom (4).
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页码:137 / 143
页数:7
相关论文
共 29 条
[1]  
Hartley F.R., The Chemistry of Organophosphorus Compounds: Phosphonium Salts, Ylides and Phosphoranes, (1993)
[2]  
Wang D., Astruc D., Chem. Rev, 115, (2015)
[3]  
Cordovilla C., Bartolome C., Martinez-Ilarduya J.M., Espinet P., ACS Catal, 5, (2015)
[4]  
Chong C.C., Hirao H., Kinjo R., Angew. Chem. Int. Ed, 127, (2015)
[5]  
Razuvaev G.A., Osanova N.A., Brilkina T.G., Zinovjeva T.I., Sharutin V.V., J. Organomet. Chem, 99, (1975)
[6]  
Barton D., Ollis W.D., Phosphorus Compounds, (1979)
[7]  
Milenkovic M., Warzajtis B., Rychlewska U., Molecules, 17, (2012)
[8]  
Pavlova J.A., Khairullina Z.Z., Tereshchenkov A.G., Antibiotics, 10, (2021)
[9]  
Tsepaeva O.V., Salikhova T.I., Grigor'eva L.R., Med. Chem. Res, 30, (2021)
[10]  
Sharutin V.V., Senchurin V.S., Sharutina O.K., Boyarkina E.A., Russ. J. Gen. Chem, 79, (2009)