Abstract
Triarylbismuth dicarboxylates p-Tol3Bi[OC(O)C6H3F2-2,3]2 (1) and m-Tol3Bi[OC(O)C6H3F2-2,3]2 (2) are synthesized by the oxidative addition reaction between triarylbismuth and 2,3-difluorobenzoic acid in the presence of tert-butyl peroxide. According to single crystal X-ray diffraction data, bismuth atoms have the coordination of a distorted trigonal bipyramid with oxygen atoms of carboxylate ligands in axial positions. Axial OBiO angles are 171.09(12)° (1) and 173.50(9)° (2). Lengths of Bi–C bonds have close values: 2.198(5)-2.213(4) Å in 1 and 2.165(3)-2.195(5) Å in 2. The Bi–O lengths (2.261(3) Å, 2.306(3) Å in 1 and 2.284(3) Å, 2.243(3) Å in 2) are comparable with the lengths of Bi–O covalent bonds. The bismuth atom is out of the [С3] equatorial plane by 0.007 Å and 0.012 Å in 1 and 2 respectively. The Bi⋯O=C distances are 2.878(5) Å, 2.953(4) Å (1) and 2.891(3) Å, 3.056(4) Å (2), which is much smaller than the sum of Van der Waals radii of Bi and O atoms of 3.9 Å. The formation of the spatial structure of the crystals of compounds 1 and 2 is governed by the occurrence of С=О⋯H, С(Ar)–Н⋯F hydrogen bonds, СН⋯π interactions, and the stacking effect.
Similar content being viewed by others
REFERENCES
A. N. Usoltsev, S. A. Adonin, A. S. Novikov, M. N. Sokolov, and V. P. Fedin. Russ. J. Coord. Chem., 2020, 46, 23. https://doi.org/10.1134/S107032842001008X
D. R. Kindra, J. K. Peterson, J. W. Ziller, and W. J. Evans. Organometallics, 2015, 34, 395. https://doi.org/10.1021/om5010786
I. J. Casely, J. W. Ziller, B. J. Mincher, and W. J. Evans. Inorg. Chem., 2011, 50, 1513. https://doi.org/10.1021/ic102119y
I. Urbanova, R. Jambor, A. Ruzicka, R. Jirasko, and L. Dostal. Dalton Trans., 2014, 43, 505. https://doi.org/10.1039/C3DT51733K
S. Solyntjes, B. Neumann, H.-G. Stammler, N. Ignatev, and B. Hoge. Eur. J. Inorg. Chem., 2016, 25, 3999. https://doi.org/10.1002/ejic.201600539
A. Soran, H. J. Breunig, V. Lippolis, M. Arca, and C. Silvestru. J. Organomet. Chem., 2010, 695, 850. https://doi.org/10.1016/j.jorganchem.2010.01.004
A. Schulz and A. Villinger. Organometallics, 2011, 30, 284. https://doi.org/10.1021/om1009796
H. J. Breunig, M. G. Nema, C. Silvestru, A. Soran, and R. A. Varga. Z. Anorg. Allg. Chem., 2010, 636, 2378. https://doi.org/10.1002/zaac.201000233
E. Alcantara, P. Sharma, D. Perez, A. Cabrera, J. Vasquez, R. Gutierrez, S. Hernandez, and A. Toscano. Synth. React. Inorg., Met.-Org., Nano-Met. Chem., 2012, 42, 1139. https://doi.org/10.1080/15533174.2012.680162
S. L. Benjamin, L. Karagiannidis, W. Levason, G. Reid, and M. C. Rogers. Organometallics, 2011, 30, 895. https://doi.org/10.1021/om1010148
C. Lichtenberg, F. Pan, T. P. Spaniol, U. Englert, and J. Okuda. Angew. Chem., Int. Ed., 2012, 51, 13011. https://doi.org/10.1002/anie.201206782
T. Obata, M. Matsumura, M. Kawahata, S. Hoshino, M. Yamada, Y. Murata, N. Kakusawa, K. Yamaguchi, M. Tanaka, and S. Yasuike. J. Organomet. Chem., 2016, 807, 17. https://doi.org/10.1016/j.jorganchem.2016.02.008
V. V. Sharutin, O. K. Sharutina, V. A. Ermakova, and Ya. R. Smagina. Russ. J. Inorg. Chem., 2017, 62, 1043. https://doi.org/10.1134/S0036023617100163
B. A. Chalmers, C. B. E. Meigh, P. S. Nejman, M. Buhl, T. Lebl, J. D. Woollins, A. M. Z. Slawin, and P. Kilian. Inorg. Chem., 2016, 55, 7117. https://doi.org/10.1021/acs.inorgchem.6b01079
C. Tschersich, S. Hoof, N. Frank, C. Herwig, and C. Limberg. Inorg. Chem., 2016, 55, 1837. https://doi.org/10.1021/acs.inorgchem.5b02740
C. R. Wade, M. R. Saber, and F. P. Gabbai. Heteroat. Chem., 2011, 22, 500. https://doi.org/10.1002/hc.20713
E. V. Novikova, A. V. Ivanov, I. V. Egorova, R. S. Troshina, N. A. Rodionova, A. I. Smolentsev, and O. N. Antzutkin. Russ. J. Coord. Chem., 2019, 45, 695. https://doi.org/10.1134/S1070328419100038
J. Chen, T. Murafuji, and R. Tsunashima. Organometallics, 2011, 30, 4532. https://doi.org/10.1021/om200228x
R. N. Duffin, V. L. Blair, L. Kedzierski, and P. C. Andrews. Dalton Trans., 2018, 47, 971. https://doi.org/10.1039/C7DT04171C
R. N. Duffin, V. L. Blair, L. Kedzierski, and P. C. Andrews. J. Inorg. Biochem., 2018, 189, 151. https://doi.org/10.1016/j.jinorgbio.2018.08.015
Y. C. Ong, V. L. Blair, L. Kedzierski, and P. C. Andrews. Dalton Trans., 2014, 43, 12904. https://doi.org/10.1039/C4DT00957F
Y. C. Ong, V. L. Blair, L. Kedzierski, K. L. Tuck, and P. C. Andrews. Dalton Trans., 2015, 44, 18215. https://doi.org/10.1039/C5DT03335G
X.-Y. Zhang, R.-X. Wu, C.-F. Bi, X. Zhang, and Y.-H. Fan. Inorg. Chim. Acta., 2018, 483, 129. https://doi.org/10.1016/j.ica.2018.07.027
K. A. Kocheshkov, A. P. Skoldinov, and N. N. Zemlyansky. Metody elementoorganicheskoi khimii. Surma, vismut (Methods of the Organometallic Chemistry. Antimony, Bismuth). Moscow: Nauka, 1976. [In Russian]
Bruker. SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System. Madison, Wisconsin, USA: Bruker AXS Inc., 1998.
Bruker. SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data. Madison, Wisconsin, USA: Bruker AXS Inc., 1998.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann. J. Appl. Crystallogr., 2009, 42, 339. https://doi.org/10.1107/S0021889808042726
A. V. Vasilev, E. V. Grinenko, A. O. Schukin, and T. G. Fedulina. Infrakrasnaya spektroskopiya organicheskikh i prirodnykh soedinenii (Infrared Spectroscopy of Organic and Natural Compounds). St. Petersburg, Russia: SPbFTU, 2007. [In Russian]
B. N. Tarasevich. IK spektry osnovnykh klassov organicheskikh soedinenii (IR Spectra of the Main Classes of Organic Compounds). Moscow: MGU, 2012. ]In Russian]
S. S. Batsanov. Russ. J. Inorg. Chem., 1991, 36, 1694.
A. Hassan and S. Wang. Dalton Trans., 1997, 12, 2009. https://doi.org/10.1039/a700477j
V. V. Sharutin, O. K. Sharutina, and A. N. Efremov. Russ. J. Inorg. Chem., 2019, 64, 190. https://doi.org/10.1134/S0036023619100139
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interests.
Additional information
Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 12, pp. 2084-2090.https://doi.org/10.26902/JSC_id84811
Rights and permissions
About this article
Cite this article
Efremov, A.N., Sharutin, V.V. & Sharutina, O.K. SYNTHESIS AND STRUCTURE OF TRIARYLBISMUTH bis(2,3-DIFLUOROBENZOATES). J Struct Chem 62, 1962–1968 (2021). https://doi.org/10.1134/S0022476621120155
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476621120155