Synthesis and Structure Features of Triphenylbismuth Dicarboxylates

L. V. Koshcheeva

Abstract


The interaction of triphenylbismuth with chloroacetic acid and pentafluorobenzoic acid in the presence of tert-butyl hydroperoxide or hydrogen peroxide in ether has led totriphenylbismuthbis(chloroacetate) (1) and  triphenylbismuthbis(2,3,4,5,6-pentafluorobenzoate) (2). The X-ray diffraction pattern for the crystal 1has been obtained at 293 K on an automatic diffractometer D8 Quest Bruker (MoKα-radiation, λ = 0.71073 Å, graphite monochromator), the results are  [C22H19O4Cl2Bi, M 627.25, the triclinic syngony, the symmetry group P–1; cell parameters: a = 8.891(5), b = 10.401(5), c = 12.452(5) Å; α = 86.38(2) degrees,β = 73.97(2) degrees., γ = 87.15(3) degrees.; V = 1104.0(9) Å3; the crystal size is 0.41×0.28×0.1 mm; intervals of reflection indexes are –15 ≤ h ≤ 15, –17 ≤ k ≤ 17, –21 ≤ l ≤ 21; total reflections 76809; independent reflections 11945; Rint 0.0525; GOOF 1.041; R1 = 0.0330, wR2 = 0.0665; residual electron density 1.30/–2.28 e/Å3], and 2 [C32H15O4F10Bi, M 862.42, the triclinic syngony, the symmetry group P–1; cell parameters: a = 12.168(8), b = 12.260(8), c = 12.720(8) Å;
α = 72.43(3) degrees, β = 63.39(3) degrees, γ = 61.46(2) degrees.; V = 1481.0(16) Å3; the crystal size is 0.37×0.2×0.1 mm; intervals of reflection indexes are –16 ≤ h ≤ 16, –16 ≤ k ≤ 16, –16 ≤ l ≤ 16; total reflections 51260; independent reflections 7342; Rint 0.0416; GOOF 1.047; R1 = 0.0251, wR2 = 0.0524; residual electron density 0.84/–0.91 e/Å3]the bismuth atoms have a distorted trigonal-bipyramidal coordination. The OBiO axial angles are 173.07(7) degrees and 172.24(8) degrees; the sums of the CBiC angles in the equatorial plane are 359.93 degrees  and 359.92 degrees. The Bi–O bond lengths are 2.303(2), 2.323(2) Å, and 2.272(3), 2.315(3) Å .The intervals of variation in the Bi–C equatorial bond lengths are 2.190(3)–2.214(3)Å and 2.194(3)–2.206(3)Å. Structures 1 and 2 contain intermolecular contacts between the bismuth atoms and the oxygen atoms of the carboxylate groups. The Bi···O=С distances equal 2.904(3), 2.908(3) Å (1), and 2.947(4), 3.167(4) Å (2), which is less than the sum of the Van der Waals radii of bismuth and oxygen (3.59 Å). The Cl∙∙∙Cl intermolecular contacts (3.43 Å) and H∙∙∙O (2.43, 2.57 Å) are present in crystal 1; while only H∙∙∙O (2.50 Å) is presentin crystal 2. Complete tables of coordinates of atoms, bond lengths and valence angles for the structure are deposited at the Cambridge Structural Data Bank (No. 1991198 (1); No. 2042930 (2); deposit@ccdc.cam.ac.uk; http: //www.ccdc.cam.ac.uk).


Keywords


hydrogen peroxide; tert-butyl hydroperoxide; triphenylbismuth; chloroacetic acid; pentafluorobenzoic acid; triphenylbismuthdicarboxylate; synthesis; structure; X-ray analysis

References


Stability and Toxicity of Tris-tolyl Bismuth(V) Dicarboxylates and Their Biological Activity Towards / Y.C. Ong, V.L. Blair, L. Kedzierski et al. // Leishmania Major. Dalton Trans. – 2015. – V. 44. – P. 18215–18226. DOI: 10.1039/c5dt03335g.

Tiekink, E.R.T. Antimony and Bismuth Compounds in Oncology / E.R.T. Tiekink // Crit. Rev. Oncol. / Hematol. – 2002. – V. 42, № 3. – P. 217–224. DOI: org/10.1016/S1040-8428(01)00217-7.

Synthesis, Characterization and in vitro Cytotoxicity Screening of Some Triarylbismuth(V) Di(N‐salicylidene)amino Carboxylates and the Crystal Structure of (2‐HOC6H4CH=NCH2CO2)2Bi(C6H5)3 / G.-C. Wang, J. Xiao, Y.-N. Lu et al. // Appl. Organomet. Chem. – 2005. – V. 19, № 1. – P. 113–117. DOI: 10.1002/aoc.749.

Synthesis, Crystal Structures, DNA Interaction and Anticancer Activity of Organobismuth(V) Complexes / L. Cui, C. Bi, Y. Fan et al. // Inorgan. Chim. Acta. – 2015. – V. 437, № 1. – P. 41–46. DOI: 10.1016/j.ica.2015.07.008.

Synthesis, Characterization and Cytotoxicity of Some Triarylbismuth(V) Di(N‐p‐toluenesulfonyl) Aminoacetates and the Crystal Structure of (4‐CH3C6H4SO2NHCH2CO2)2Bi(C6H4Cl‐4)3 / L.Yu, Y.-Q. Ma, G.-C. Wang et al. // Appl. Organomet. Chem. – 2004. – V. 18, № 4. – P. 187–190. DOI: 10.1002/aoc.609.

Comparative Stability, Toxicity and Anti-leishmanial Activity of Triphenyl Antimony(V) and Bismuth(V) α-Hydroxy Carboxylato Complexes / R.N. Duffin, V.L. Blair, L. Kedzierski et al. // Dalton Trans. – 2018. – V. 47. – P. 971–980. DOI: 10.1039/C7DT04171C.

Cambridge Crystallographic Data Center. 2019. (deposit@ccdc.cam.ac.uk; http://www.ccdc.cam.ac.uk).

Шарутин, В.В. Синтез и строение дикарбоксилатов три-мета-толилвисмута / В.В. Шару-тин, О.К. Шарутина, В.С. Сенчурин // Журн. неорган. химии. – 2014. – Т. 59, № 1. – С. 42–46. DOI: 10.7868/S0044457X14010164.

Андреев, П.В. Строение аддукта бис(хлорацетата) три(о-толил)висмута с хлоруксусной кислотой / П.В. Андреев // Вестник ЮУрГУ. Серия «Химия». – 2019. – Т. 11, № 3. – С. 59–65. DOI: 10.14529/chem190307.

Синтез и строение бис(фторбензоатов) трифенилвисмута / В.В. Шарутин, И.В. Егорова, О.К. Шарутина и др. // Коорд. химия. – 2003. – Т. 29, № 7. – С. 496–501.

Шарутин, В.В. Дикарбоксилаты триарилвисмута Ar3Bi[OC(O)R]2, Ar = p-Tol, R = CH2Cl; Ar = Ph, R = C6Н4OMe-2, CН=CHPh / В.В. Шарутин, О.К. Шарутина, А.Н. Ефремов // Журн. неор-ган. химии. – 2019. – Т. 64, № 2. – С. 159–164. DOI: 10.1134/S0044457X19020181.

Decomposition of Triphenylbismuth Dicrotonate in Light in the Presence of 2-Methyl-2- nitrosopropane / A.V. Gushchin, O.S. Kalistratova, A.I. Maleeva, V.A. Kuropatov // Вестник ЮУрГУ. Серия «Химия». – 2016. – Т. 8, № 1. – С. 51–56. DOI: 10.14529/chem160108.

Гущин, А.В. Синтез и строение диметакрилата трифенилсурьмы / А.В. Гущин, Д.В. Шашкин, Л.К. Прыткова и др. // Журн. общ. химии. – 2011. – Т. 81, № 3. – С. 397–400.

Шарутин, В.В. Синтез и строение бис(1-адамантанкарбоксилата) трифенилвисмута / В.В. Шарутин, В.С. Сенчурин, О.К. Шарутина / Журн. неорган. химии. – 2011. – Т. 56, № 10. – С. 1644–1646.

Синтез и структура бис[3-(2-фурил)акрилата]трифенилвисмута Ph3Bi[O2CCH=CH(C4H3O)]2 и ди-мета-нитроциннамата трифенилвисмута Ph3Bi(O2CCH=CH–C6H4NO2-м)2 / А.А. Гусаковская, О.С. Калистратова, П.В. Андреев и др. // Кристаллография. –2018. – Т. 63, № 2. – С. 203–207. DOI: 10.7868/S0023476118020066.

Синтез и строение дикарбоксилатов трис(5-бром-2-метоксифенил)висмута: [(C6H3(Br-5)(MeO-2)]3Bi[OC(O)CHal3]2 (Hal = F, Cl) / В.В. Шарутин, О.К. Шарутина, В.А. Ермакова и др. // Журн. неорган. химии. – 2017. – Т. 62, № 8. – С. 1049–1056. DOI: 10.7868/S0044457X17080050.

Comparative Stability, Toxicity and Anti-Leishmanial Activity of Triphenyl Antimony(V) and Bismuth(V) α-Hydroxy Carboxylato Complexes / R.N. Duffin, V.L. Blair, L. Kedzierski, P.C. Andrews // Dalton Trans. – 2018. – V. 47. – P. 971–980. DOI: 10.1039/c7dt04171c.

Comparative Stability, Cytotoxicity and Anti-Leishmanial Activity of Analogous Organometallic Sb(V) and Bi(V) Acetato Complexes: Sb Confirms Potential While Bi Fails The Test / R.N. Duffin, V.L. Blair, L. Kedzierski, P.C. Andrews // J. Inorg. Biochem. – 2018. – V. 189. – P. 151–162. DOI: 10.1016/j.jinorgbio.2018.08.015.

Stability and Toxicity of Heteroleptic Organometallic Bi(V) Complexes Towards Leishmania Major / Y.C. Ong, V.L. Blair, L. Kedzierski, P.C. Andrews // Dalton Trans. 2014. – V. 43. – P. 12904 – 12916. DOI: 10.1039/c4dt00957f.

Stability and Toxicity of Tris-Tolyl Bismuth(V) Dicarboxylates and their Biological Activity Towards Leishmania Major / Y.C. Ong, V.L. Blair, L. Kedzierski et al. // Dalton Trans. –2015. – V. 44. – P. 18215–18226. DOI: 10.1039/c5dt03335g.

Facile One-Pot Synthesis of Triphenylbismuth(V) Bis(carboxylate) Complexes / I. Kumar, P. Bhattacharya, K.H. Whitmire // Organometallics. – 2014. – V. 33. – P. 2906–2909. DOI: 10.1021/om500337z.

Bruker. SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.

Bruker. SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Dis-playing Crystal Structures From Diffraction Data. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.

OLEX2: Complete Structure Solution, Refinement and Analysis Program / O.V. Dolomanov, L.J. Bourhis, R.J. Gildea et al. // J. Appl. Cryst. – 2009. – V. 42. – P. 339–341. DOI: 10.1107/S0021889808042726.

Synthesis, Crystal Structures, DNA Interaction and Anticancer Activity of Organobismuth(V) Complexes / L. Cui, C. Bi, Y. Fan et al. // Inorg. Chim. Acta. – 2015. – V. 437. – P. 41–46. DOI: 10.1016/j.ica.2015.07.008.

Triphenylbismuth(V) Di[(iso)nicotinates] – Transmetallation Agents or Divergent Organometalloligands? First Organobismuth(V)-Based Silver(I) Coordination Polymers / A.B. Kiran, T. Mocanu, A. Pollnitz et al. // Dalton Trans. – 2018. – V. 47. – P. 2531–2542. DOI: 10.1039/C7DT04516F.

A New Organobismuth(V) Complex with Fluorobenzoic Ligands: Synthesis, Crystal Structure, Photodegradation Properties / X.-Y. Zhang, R.-X. Wu, C.-F. Bi et al. // Inorg. Chim. Acta. – 2018. –V. 483. – P. 129–135. DOI: 10.1016/j.ica.2018.07.027.

Synthesis and Structural Study of Triphenylbismuth Bis(salicylate) / K. Feham, A. Benkadari, A. Chouaih et al. // Cryst. Struct. Theory Appl. – 2013. – V. 2. – P. 28–33. DOI: 10.4236/csta.2013.21004

Synthesis and Structure of Triphenylbismuth Bis(3-phenylprop-2-enoate) / P.V. Andreev, N.V. Somov, O.S. Kalistratova et al. // Crystallogr. Rep. – 2015. – V. 60. – P. 517–520. DOI: 10.1134/S1063774515040057.

Шарутин, В.В. Синтез и строение бис(2-фениламинобензоата) трифенилвисмута / В.В. Шарутин, И.В. Егорова, М.А. Казаков и др. // Журн. неорган. химии. – 2009. – Т. 54, № 7. – С. 1156–1159.

Особенности строения дикарбоксилатов трифенилвисмута / В.В. Шарутин, Т.К. Иванен-ко, Н.А. Николаева, А.А. Молоков, Г.К. Фукин // Коорд. химия. – 2006. – Т. 32, № 9. – С. 672–679.

Шарутин, В.В. Синтез и строение бис(фенилкарборанилкарбоксилата) трифенилвисмута / В.В. Шарутин, В.С. Сенчурин, О.К. Шарутина и др. // Журн. общ. химии. – 2010. – Т. 80, № 10. – С. 1630–1633.

Шарутин, В.В Синтез и строение бис(3,4-диметилбензолсульфоната) триc(3-метилфенил)висмута / В.В. Шарутин, О.К. Шарутина // Журн. общ. химии. – 2016. – Т. 86, № 5. – С. 811–814.

Шарутин, В.В. Синтез и строение бис(3,4-диметилбензолсульфоната) трифенилвисмута / В.В Шарутин, О.К. Шарутина, В.С. Сенчурин // Журнал. неорган. химии. – 2016. – Т. 61, № 3. – С. 334–337. DOI: 10.7868/S0044457X16030211.

Consistent Van der Waals Radii for the Whole Main Group / M. Mantina, A.C. Chamberlin, R. Valero et al. // J. Phys. Chem. A. – 2009. – V. 113, iss. 19. – P. 5806–5812. DOI: 10.1021/jp8111556.


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