Synthesis and Structure of Cyclopentadienyl Diferrocenoylacetonatozirconium Chloride С5H5[С10H9FeC(O)CHC(O)CF3]2ZrCl
Keywords:
zirconocene dichloride, ferrocenoyltrifluoroacetylacetone, complex, X-ray diffraction analysisAbstract
Interaction of zirconocene dichloride with ferrocenoyltrifluoroacetylacetone in benzene solution led to synthesis of a trans-isomer of cyclopentadienyl diferrocenoylacetonatozirconium chloride, the structure of which was proved by X-ray diffraction analysis. According to the X-ray analysis performed at 293 K on an automatic four-circle diffractometer D8 QuestBruker (MoCA radiation, λ = 0.71073 Å, graphite monochromator), the zirconium atoms in the trans-isomer of complex 1 have a distorted octahedral configuration [C33H25F6ClFe2ZrO4 (1), M 837.90; the crystal structure is triclinic, the symmetry group P ; crystal unit cell parameters: a = 10.16(3),
b = 12.39(3), c = 13.44 (3) Å; α= 95.70(10)º, β = 102.62(14)º, γ = 93.77(2)° ; V = 1635 (6) Å3; crystal size 0.16 × 0.09 × 0.08 mm3; reflection index intervals –12 ≤ h ≤ 12, –15 ≤ k ≤ 15,
–17 ≤ l ≤ 17; total reflections 23770; independent reflections 7090; Rint = 0.3164; GOOF = 1.054; R1 = 0.1601, wR2 = 0.3121; residual electron density 1.41/–1.80 e/Å3. In the IR spectrum of compound 1 the bands are observed at 808, 1007, 1055, 1409, 2855, 2926, 3099 cm–1, which can be attributed to fluctuations in the bonds of the ferrocene substituent. The intense vibration band at 1298 cm–1 corresponds to the vibrations of the CF3 groups. Valence vibrations of the Zr-O bonds appear in the IR spectrum as a series of bands in the region of 400–1000 cm–1. According to the X-ray diffraction analysis, the packing of complex 1 molecules into layers is possible due to short contacts С···С (3.323 Å). Each of the layers is formed by reference contacts Н···С (2.850 Å). Complete tables of atomic coordinates, bond lengths, and valence angles are deposited in the Cambridge structural data Bank (No. 1988379 for 1; deposit@ccdc.cam.ac.uk; http://www.ccdc.cam.ac.uk).
References
Джемилев, У.М. Комплексы циркония в синтезе и катализе / У.М. Джемилев, О.С. Востри-кова, А.Г. Ибрагимов // Успехи химии. – 1986. – Т. 2. – С. 191 – 224.
Schwartz, I. Hydrozirconation: A New Transition Metal Reagent for Organic Synthesis / I. Schwartz, J. Labinger // Angew. Chem. Int. Ed. Engl. – 1976. – V. 15. – P. 333–340. DOI: 10.1002/anie.197603331
Schwartz, J. Organozirconium Compounds in Organic Synthesis: Cleavage Reactions of Carbon-zirconium Bonds / J. Schwartz // Pure Appl. Chem. – 1980. – V. 52. – P. 733–740. DOI: 10.1351/pac198052030733
Rogers, J.S. Ethoxyboratabenzene Zirconium Complexes: Catalysts for α-Olefin Production / J.S. Rogers, G.C. Bazan, C.K. Sperry // J. Am. Chem. Soc. – 1997. – V. 119. – P. 9305–9306. DOI: 10.1021/ja971976n
Novel Zirconium Complexes with Constrained Cyclic β-Enaminoketonato Ligands: Improved Catalytic Capability Toward Ethylene Polymerization / K.-T. Wang, Y.-X. Wang, B. Wang et al. // Dal-ton Trans. – 2016. – V. 45. – P. 10308–10318. DOI: 10.1039/C6DT01391K
Zirconium Enolatoimine Complexes in Olefin Polymerization / S.M. Yu, U. Tritschler, I. Göttker-Schnetmann et al. // Dalton Trans. – 2010. – V. 39. – P. 4612–4618. DOI: 10.1039/B916289E
Titanium and Zirconium Permethylpentalene Complexes, Pn*MCpRX, as Ethylene Polymeriza-tion Catalysts / D.A.X. Fraser, Z.R. Turner, J.-Ch. Buffet, D. O’Hare // Organometallics. – 2016. – V. 35. – P. 2664–2674. DOI: 10.1021/ acs.organomet.6b00417
Highly Active and Isospecific Styrene Polymerization Catalyzed by Zirconium Complexes Bear-ing Aryl-substituted [OSSO]-Type Bis(phenolate) Ligands / N. Nakata, T. Toda, Y. Saito et al. // Poly-mers. – 2016. – V. 8. – P. 31–41. DOI: 10.3390/polym8020031
Theaker, G.W. Zirconium-Catalyzed Polymerization of a Styrene: Catalyst Reactivation Mecha-nisms Using Alkenes and Dihydrogen / G.W. Theaker, C. Morton, P. Scott // Macromolecules. – 2011. – V. 44. – P. 1393–1404. DOI: 10.1021/ma102835p
Catalytically Active N-Acylamidine–Zirconium Complexes: Synthesis, Structures, and Application in Ethylene Polymerization / Th. Holtrichter-Rößmann, I. Häger, C.-G. Daniliuc et al. // Organo-metallics. – 2016. – V. 35. – P. 1906–1915. DOI: 10.1021/ acs.organomet.6b00240
Cuenca, T. Dicyclopentadienyl-titanium and -Zirconium Complexes as Catalysts for Hydrogenation of Olefins / T. Cuenca, J.C. Flores, P. Royo // J. Organomet. Chem. – 1993. – V. 462. – P. 191–201. DOI: 10.1016/0022- 328X(93)83357-2
Stoichiometric Reactions and Catalytic Hydrogenation with a Reactive Intramolecular Zr+/Amine Frustrated Lewis Pair / X. Xu, G. Kehr, C.G. Daniliuc, G. Erker // J. Am. Chem. Soc. – 2015. – V. 137. – P. 4550–4557. DOI: 10.1021/jacs.5b01623
Highly Enantioselective Friedel−Crafts Alkylations of Indoles with Simple Enones Catalyzed by Zirconium(IV)−BINOL Complexes† / G. Blay, I. Fernandez, A. Monleon et al. // Org. Lett. – 2007. – V. 9. – P. 2601–2604. DOI: 10.1021/ol0710820
Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones / G. Blay, I. Fernandez, A. Monleon et al. // Org. Lett. – 2009. – V. 11. – P. 441–444. DOI: 10.1021/ol802509m
Mo, L.-P. Recent Applications of Zirconium Compounds as Catalysts or Reagents in Organic Synthesis / L.-P. Mo, Zh.-H. Zhang // Curr. Org. Chem. – 2011. – V. 15. – P. 3800–3823. DOI: 10.2174/138527211797884520
[Na-15-Krone-5]2[ZrF2Cl4] und (PPh4)2[ZrCl6] • 2 CH2Cl2; Synthesen, IR-Spektren und Kristallstrukturen / [Na-15-Crown-5]2[ZrF2Cl4] and (PPh4)2[ZrCl6] • 2 CH2Cl2; Syntheses, IR Spectra, and Crystal Structures / Hartmann E., Dehnicke K., Fenske D. et al. // Z. Naturforsch., B: Chem. Sci. – 1989. – V. 44. – P. 1155–1160. DOI: 10.1515/znb-1989-1001
Chen, L. Synthesis, Structure, and Reactivity of [Zr6Cl18H5]2–, the First Paramagnetic Species of Its Class / L. Chen, F.A. Cotton // Inorg. Chem. – 1996. – V. 35. – P. 7364–7369. DOI: 10.1021/ic960454q
Chen, L. Synthesis and Structural Characterization of Compounds Containing the [Zr6Cl18H5]3–Cluster Anion. Determination of the Number of Cluster Hydrogen Atoms / L. Chen, F.A. Cotton, W.F. Wojtczak // Inorg. Chem. – 1997. – V. 36. – P. 4047–4054. DOI: 10.1021/ic960173i
Synthesis and Structure of (Ph4P)2MCl6 (M = Ti, Zr, Hf, Th, U, Np, Pu) / S.G. Minasian, K.S. Boland, R.K. Feller et al. // Inorg. Chem. – 2012. – V. 51. – P. 5728–5736. DOI: 10.1021/ic300179d
Шарутин, B.B. Синтез и строение комплексов циркония [Ph3PR]+2 [ZrCl6]2–, R = Et, CH2Ph, CH2C(O)OMe / В.В. Шарутин, О.К. Шарутина, Е.В. Лобанова // Журн. неорган. химии. – 2018. – Т. 63. – № 12. – С. 15491554. DOI: 10.1134/S0044457X1812019X
Андреев, П.В. Синтез и строение комплексов циркония [Ph3PCH=CHMe]2[ZrCl6] и гафния [Ph3PCH2C(O)Me]2[HfCl6] / П.В. Андреев, Е.В. Лобанова, П.Д. Дрожилкин // Вестник ЮУрГУ. Серия «Химия». – 2019. – Т. 11, № 4. – С. 26–33. DOI: 10.14529/chem190403
Sharutin, V.V. Synthesis and Structure of Triphenylbut-2-enyl- and Triphenylmetoxymethylphosphonium Hexachlorozirconates / V.V. Sharutin, O.K. Sharutina, N.M. Tarasova, E.V. Lobanova, P.V. Andreev // Bulletin of the Institutions of Higher Education, Chemistry and Chemical Technology. – 2019. – V. 62. – № 6. – Р. 36–40. DOI: 10.6060/ivkkt.20196206.5885
Sharutin, V.V. Synthesis and Structures of Zirconium Complexes [Et2H2N]+2[ZrCl6]2–, [Me3NCH2Ph]+2[ZrCl6]2–•MeCN, [Ph3PC6H4(CHPh2-4)]+2[ZrCl6]2–•2MeCN, and [Ph4Sb]+2[ZrCl6]2– / V.V. Sharutin, O.K. Sharutina, N.M. Tarasova, O.S. El′tsov // Russ. Chem. Bull. – 2019. – V. 68. – № 1. – Р. 24–31. DOI: 10.1007/s11172-019-2411-9
Ferrocenyl Derivatives of Dicyclopentadienyl-titanium, -Zirconium and –Hafnium / G.A. Razuvaev, G.A. Domrachev, V.V. Sharutin, O.N. Suvorova // J. Organomet. Chem. – 1975. – V. 141. – P. 313317.
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 Displaying Crystal Structures From Diffraction Data. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
OLEX2: a 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.
Фрейдлина, Р.Х. Синтез смешанных клешнеобразных циклопентадиенильных соединений циркония / Р.Х. Фрейдлина, Э.М. Брайнина, А.Н. Несмеянов // Докл. АН СССР. – 1961. – Т. 138. – С. 13691373.
Товбис, М.С. Методы анализа и идентификации органических соединений: описание практических работ для студентов направления 04.06.01 «Химические науки» направленности «Органическая химия», очной и заочной форм обучения / М.С. Товбис // Мин-во науки и высш. образования Рос. Федерации, Сиб. гос. ун-т науки и технологий им. акад. М. Ф. Решетнева. – Красноярск: СибГУ им. М.Ф. Решетнева, 2019. – 35 с.
Синтез и сравнительный анализ пористых бинарных оксидов ZrО2 – SiО2, синтезированных на основе хлорокиси циркония (IV) и тетрабутоксициркония с использованием в качестве матрицы целлюлозы / А.Б. Шишмаков, О.В. Корякова, Ю.В. Микушина, Л.А. Петров // Химия растительного сырья. – 2015. – № 3. – С. 151–159. DOI:10.14258/jcprm.201503599
Dunitz, J.D. The Crystal Structure of Ferrocene / J.D. Dunitz, L.E. Orgel, A. Rich // Acta Crystallogr. – 1956. – V. 9. – P. 373–375. DOI: 10.1107/S0365110X56001091
Seiler, P. A New Interpretation of the Disordered Crystal Structure of Ferrocene / P. Seiler, J.D. Dunitz // Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. – 1979. – B35. – P. 1068–1074. DOI: 10.1107/S0567740879005598
Covalent Radii Revisited / B. Cordero, V. Gόmez, A.E. Platero-Prats et al. // Dalton Trans. – 2008. – P. 2832–2838. DOI: 10.1039/b801115j
The New Method of Synthesis and Structural Identification of Cis-[CpZr(acac)2Cl] / S.S. Yun, Il-H. Suh, Eu. Hee Kim et al. // J. Korean Chem. Soc. – 1999. – V. 43. – P. 593–595.
Crystal Structure of Chlorocyclopentadienyl-bis(1,3-diphenyl-1,3-propanedionato)zirconium (IV) Complex / S. Lee, S.K. Kang, S.S. Yun et al. // Bull. Korean Chem. Soc. – 2005. – V. 26. – P. 852–854. DOI: 10.5012/bkcs.2005.26.5.852
