Abstract
A novel sterically hindered o-benzoquinone 4,6-di-tert-butyl-3-(5,7-di-tert-butylbenzooxazole-2-yl)-o-benzoquinone containing a benzoxazole moiety is prepared. The interaction of this quinone with Cu(0) yielded a cubane copper(II) complex with a Cu4O4 core. Molecular and crystal structures of the o-quinone (CCDC 2269708) and the copper complex (CCDC 2269709) are determined by XRD.
Similar content being viewed by others
REFERENCES
A. V. Pestov, P. A. Slepukhin, and V. N. Charushin. Copper and nickel chelate complexes with polydentate N,O-ligands: structure and magnetic properties of polynuclear complexes. Russ. Chem. Rev., 2015, 84, 310-333. https://doi.org/10.1070/RCR4461
B. Yang, J. Pan, X. Meng, J. Cao, Y. Li, F. Xiao, and D. Li. Tetracopper complexes with two-mode cubane-like Cu4O4 core from similar hydroxyl-rich salicylaldehyde Schiff bases: Structure and magnetic properties. Polyhedron, 2016, 110, 182-187. https://doi.org/10.1016/j.poly.2016.02.042
R. R. Tripathy, S. Singha, and S. Sarkar. A review on bio-functional models of catechol oxidase probed by less explored first row transition metals. J. Coord. Chem., 2022, 75, 1967-2017. https://doi.org/10.1080/00958972.2022.2122053
E. I. Solomon, D. E. Heppner, E. M. Johnston, J. W. Ginsbach, and J. Cirera. Copper active sites in biology. Chem. Rev., 2014, 114, 3659-3853. https://doi.org/10.1021/cr400327t
X. Jiang, J. Li, B. Yang, X.-Z. Wei, B.-W. Dong, Y. Kao, M.-Y. Huang, C.-H. Tung, and L.-Z. Wu. A bio-inspired Cu4O4 cubane: Effective molecular catalysts for electrocatalytic water oxidation in aqueous solution. Angew. Chem., Int. Ed., 2018, 57, 7850-7854. https://doi.org/10.1002/anie.201803944
K. V. N. Esguerra and J.-P. Lumb. Selectivity in the aerobic dearomatization of phenols: total synthesis of dehydronornuciferine by chemo- and regioselective oxidation. Angew. Chem., Int. Ed., 2018, 57, 1514-1518. https://doi.org/10.1002/anie.201710271
O. V. Nesterova, A. J. L. Pombeiro, and D. S. Nesterov. Tetranuclear copper complexes with bulky aminoalcohol ligands as catalysts for oxidative phenoxazinone synthase-like coupling of aminophenol: A combined experimental and theoretical study. Catalysts, 2022, 12, 1408. https://doi.org/10.3390/catal12111408
M. Henrion, Y. Mohr, K. Janssens, S. Smolders, A. L. Bugaev, O. A. Usoltsev, E. A. Quadrelli, F. M. Wisser, D. E. De Vos, and J. Canivet. Reusable copper catechol-based porous polymers for the highly efficient heterogeneous catalytic oxidation of secondary alcohols. ChemCatChem, 2022, 14, e2022006. https://doi.org/10.1002/cctc.202200649
S. Sagar, S. Sengupta, A. J. Mota, S. K. Chattopadhyay, A. E. Ferao, E. Riviere, W. Lewis, and S. Naskar. Cubane-like tetranuclear Cu(II) complexes bearing a Cu4O4 core: Crystal structure, magnetic properties, DFT calculations and phenoxazinone synthase like activity. Dalton Trans., 2017, 46, 1249-1259. https://doi.org/10.1039/C6DT03754B
C. Mukherjee, T. Weyhermüller, E. Bothe, E. Rentschler, and P. Chaudhuri. A tetracopper(II)-tetraradical cuboidal core and its reactivity as a functional model of phenoxazinone synthase. Inorg. Chem., 2007, 46, 9895-9905. https://doi.org/10.1021/ic7012599
R. Sanyal, S. Ketkov, S. Purkait, F. A. Mautner, G. Zhigulin, and D. Das. Nuclearity dependent solvent contribution to the catechol oxidase activity of novel copper(II) complexes derived from Mannich-base ligand platforms: Synthesis, crystal structure and mechanism. New J. Chem., 2017, 41, 8586-8597. https://doi.org/10.1039/C7NJ00425G
W. Kaim. The chemistry and biochemistry of the copper–radical interaction. Dalton Trans., 2003, 5, 761-768. https://doi.org/10.1039/B210193A
P. Verma, J. Weir, L. Mirica, and T. D. P. Stack. Tale of a twist: Magnetic and optical switching in copper(II) semiquinone complexes. Inorg. Chem., 2011, 50, 9816-9825. https://doi.org/10.1021/ic200958g
R. A. Davidson, J. Hao, A. L. Rheingold, and J. S. Miller. High spin ground state copper(II) and nickel(II) complexes possessing the 3,5-di-tert-butyl-1,2-semiquinonate radical anion. Polyhedron, 2017, 133, 348-357. https://doi.org/10.1016/j.poly.2017.05.038
V. I. Ovcharenko, E. V. Gorelik, S. V. Fokin, G. V. Romanenko, V. N. Ikorskii, A. V. Krashilina, V. K. Cherkasov, and G. A. Abakumov. Ligand effects on the ferro- to antiferromagnetic exchange ratio in bis(o-semiquinonato)copper(II). J. Am. Chem. Soc., 2007, 129, 10512-10521. https://doi.org/10.1021/ja072463b
G. Speier, Z. Tyeklár, P. Tóth, E. Speier, S. Tisza, A. Rockenbauer, A. M. Whalen, N. Alkire, and C. G. Pierpont. Valence tautomerism and metal-mediated catechol oxidation for complexes of copper prepared with 9,10-phenanthrenequinone. Inorg. Chem., 2001, 40, 5653-5659. https://doi.org/10.1021/ic010373g
G. A. Abakumov, V. K. Cherkasov, V. I. Nevodchikov, V. A. Kuropatov, G. T. Yee, and C. G. Pierpont. Magnetic properties and redox isomerism for 4,4′-bis(semiquinone) complexes of copper. Inorg. Chem., 2001, 40, 2434-2436. https://doi.org/10.1021/ic001449w
J. Rall, M. Wanner, M. Albrecht, F. M. Hornung, and W. Kaim. Sensitive valence tautomer equilibrium of paramagnetic complexes [(L)Cun+(Qn−)] (n = 1 or 2; Q = quinones) related to amine oxidase enzymes. Chem. Eur. J., 1999, 5, 2802-2809. https://doi.org/10.1002/(sici)1521-3765(19991001)5:10%3c2802::aid-chem2802%3e3.0.co;2-5
L. M. Berreau, S. Mahapatra, J. A. Halfen, R. P. Houser, J. V. G. Young, and W. B. Tolman. Reactivity of peroxo- and bis(μ-oxo)dicopper complexes with catechols. Angew. Chem., Int. Ed., 1999, 38, 207-210. https://doi.org/10.1002/(sici)1521-3773(19990115)38:1/2%3c207::aid-anie207%3e3.0.co;2-u
A. A. Karasik, A. V. Krashilina, A. T. Gubaidullin, I. A. Litvinov, V. K. Cherkasov, O. G. Sinyashin, and G. A. Abakumov. Synthesis, structures, and properties of 3,6-di-tert-butyl-o-benzosemiquinone complexes of copper(I) with 1,5-diaza-3,7-diphosphacyclooctanes. Russ. Chem. Bull., 2000, 49, 1782-1788. https://doi.org/10.1007/BF02496354
G. A. Abakumov, A. V. Krashilina, V. K. Cherkasov, I. L. Eremenko, and S. E. Nefedov. Bis(1,4-di-tert-butyl-1,4-diazabutadiene)copper(I) [(3,6-di-tert-butyl-o-benzosemiquinono)(3,6-di-tert-butyl-catecholato)cuprate(II)]. The molecular structure and intramolecular electron transfer. Russ. Chem. Bull., 2001, 50, 2193-2199. https://doi.org/10.1023/A:1015022006445
R. M. Buchanan, C. Wilson-Blumenberg, C. Trapp, S. K. Larsen, D. L. Greene, and C. G. Pierpont. Counter ligand dependence of charge distribution in copper-quinone complexes. Structural and magnetic properties of (3,5-di-tert-butylcatecholato)(bipyridine)copper(II). Inorg. Chem., 1986, 25, 3070-3076. https://doi.org/10.1021/ic00237a029
H. Börzel, P. Comba, and H. Pritzkow. Structural studies on dicopper(II) compounds with catechol oxidase activity. Chem. Commun., 2001, 1, 97/98. https://doi.org/10.1039/B008714I
M. H. Noamane, S. Ferlay, R. Abidi, N. Kyritsakas, and M. W. Hosseini. Formation of binuclear neutral copper(II) complexes based on p-tert-butyl-calix[4]arene and thiacalix[4]arene in 1,3-A conformation bearing four catechols at their lower rim. Inorg. Chim. Acta, 2017, 468, 260-269. https://doi.org/10.1016/j.ica.2017.04.047
Q. Zhao, Z.-L. Wei, Q.-P. Kang, H. Zhang, and W.-K. Dong. Homo- and heterometallic Cu(II)–M(II) (M = Ca, Sr and Ba) bis(salamo)-based complexes: Syntheses, structures and fluorescent properties. Spectrochim. Acta, Part A, 2018, 203, 472-480. https://doi.org/10.1016/j.saa.2018.06.007
M. M. Olmstead, P. P. Power, G. Speier, and Z. Tyeklár. Synthesis and structure of a tetranuclear copper(II) 3,5-di-tert-butylcatecholate pyridine complex, [Cu(DTBC)Py]4·2CH3CN. Polyhedron, 1988, 7, 609-614. https://doi.org/10.1016/S0277-5387(00)80367-8
Y. T. Tesema, D. M. Pham, and K. J. Franz. Synthesis and characterization of copper(II) complexes of cysteinyldopa and benzothiazine model ligands related to pheomelanin. Inorg. Chem., 2006, 45, 6102-6104. https://doi.org/10.1021/ic060262n
E. Gojon, J. Gaillard, J. M. Latour, and J. Laugier. Structural and magnetic properties of a novel pentacopper(II) cluster involving a trinucleating catechol ligand. Inorg. Chem., 1987, 26, 2046-2052. https://doi.org/10.1021/ic00260a008
S. Shit, M. Nandy, G. Rosair, M. Salah El Fallah, J. Ribas, E. Garribba, and S. Mitra. A hexanuclear copper(II) Schiff base complex incorporating rare “bicapped cubane” core: Structural aspects, magnetic properties and EPR study. Polyhedron, 2013, 52, 963-969. https://doi.org/10.1016/j.poly.2012.07.016
P. Padnya, K. Shibaeva, M. Arsenyev, S. Baryshnikova, O. Terenteva, I. Shiabiev, A. Khannanov, A. Boldyrev, A. Gerasimov, D. Grishaev, Y. Shtyrlin, and I. Stoikov. Catechol-containing schiff bases on thiacalixarene: synthesis, copper(II) recognition, and formation of organic-inorganic copper-based materials. Molecules, 2021, 26, 2334. https://doi.org/10.3390/molecules26082334
E. Gojon, J.-M. Latour, S. J. Greaves, D. C. Povey, V. Ramdas, and G. W. Smith. Syntheses, and structural, magnetic, and redox properties of multinuclear copper catecholates. Dalton Trans., 1990, 7, 2043-2051. https://doi.org/10.1039/DT9900002043
E. Gojon, S. J. Greaves, J. M. Latour, D. C. Povey, and G. W. Smith. ChemInform abstract: X-ray structural characterization and magnetic properties of a novel tetranuclear copper catecholate. Inorg. Chem., 1987, 26, 1457. https://doi.org/10.1021/ic00256a029
W.-K. Dong, X.-N. He, H.-B. Yan, Z.-W. Lv, X. Chen, C.-Y. Zhao, and X.-L Tang. Synthesis, structural characterization and solvent effect of copper(II) complexes with a variational multidentate Salen-type ligand with bisoxime groups. Polyhedron, 2009, 28, 1419-1428. https://doi.org/10.1016/j.poly.2009.03.017
K.-Q. Hu, S.-Q. Wu, G.-Y. An, A.-L. Cui, and H.-Z. Kou. Syntheses, structure, and magnetic properties of heteronuclear Cu(II)4Fe(III)4 cluster and Cu(II)8 bimetallacycles. Dalton Trans., 2013, 42, 1102-1108. https://doi.org/10.1039/C2DT31708G
M. Sutradhar, M. V. Kirillova, M. F. C. Guedes da Silva, C.-M. Liu, and A. J. L. Pombeiro. Tautomeric effect of hydrazone Schiff bases in tetranuclear Cu(II) complexes: magnetism and catalytic activity towards mild hydrocarboxylation of alkanes. Dalton Trans., 2013, 42, 16578-16587. https://doi.org/10.1039/C3DT52453A
W. L. F. Armarego and C. L. L. Chai. Purification Laboratory Chemicals. Amsterdam, Netherlands: Elsevier, Butterworth-Heinemann, 2003.
M. V. Arsenyev, E. V. Baranov, A. Y. Fedorov, S. A. Chesnokov, and G. A. Abakumov. New bis-o-quinone with azine spacer and its cyclization into indazolo[2,1-a]indazole system. Mendeleev Commun., 2015, 25, 312-314. https://doi.org/10.1016/j.mencom.2015.07.029
V. I. Lodyato, I. L. Yurkova, V. L. Sorokin, O. I. Shadyro, V. I. Dolgopalets, and M. A. Kisel. Synthesis and properties of 11-(3,5-di-tert-butyl-2-hydroxyphenylcarbamoyl)undecanoic acid (VII), a new amphiphilic antioxidant. Bioorg. Med. Chem. Lett., 2003, 13, 1179. https://doi.org/10.1002/chin.200328102
Data Collection, Reduction and Correction Program, CrysAlisPro 1.171.35.19, Software Package. Rigaku OD, 2011.
Bruker, APEX3. Bruker Molecular Analysis Research Tool, v. 2018.7-2. Madison, Wisconsin, USA: Bruker AXS, 2018.
Bruker, SAINT Data Reduction and Correction Program, v. 8.37A. Madison, Wisconsin, USA: Bruker AXS, 2012.
G. M. Sheldrick. SHELXS-97, Program for Crystal Structure Solution. University of Göttingen: Göttingen, 1997.
G. M. Sheldrick. SHELXT, Integrated space-group and crystal-structure determination. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71(1), 3-8. https://doi.org/10.1107/s2053273314026370
G. M. Sheldrick. SHELXTL. Version 6.14. Structure Determination Software Suite. Madison, Wisconsin, USA: Bruker AXS, 2003.
G. M. Sheldrick. Crystal structure refinement with SHELXL. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71(1), 3-8. https://doi.org/10.1107/s2053229614024218
SCALE3 ABSPACK: Empirical absorption correction, CrysAlisPro 1.171.35.19, Software Package. Rigaku OD, 2011.
G. M. Sheldrick. SADABS v.2016/2, Bruker/Siemens Area Detector Absorption Correction Program. Madison, Wisconsin, USA: Bruker AXS, 2016.
L. Krause, R. Herbst-Irmer, G. M. Sheldrick, and D. Stalke. Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination. J. Appl. Crystallogr., 2015, 48, 3-10. https://doi.org/10.1107/S1600576714022985
T. V. Astaf′eva, M. V. Arsenyev, R. V. Rumyantcev, G. K. Fukin, V. K. Cherkasov, and A. I. Poddelsky. Imine-based catechols and o-benzoquinones: synthesis, structure, and features of redox behavior. ACS Omega, 2020, 5, 22179-22191. https://doi.org/10.1021/acsomega.0c02277
M. V. Arsenyev, E. V. Baranov, S. A. Chesnokov, V. K. Cherkasov, and G. A. Abakumov. Synthesis and structure of Schiff bases based on 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde. New sterically hindered bis-catecholaldimines. Russ. Chem. Bull., 2013, 62, 2394-2400. https://doi.org/10.1007/s11172-013-0347-z
I. V. Smolyaninov, D. A. Burmistrova, M. V. Arsenyev, N. R. Almyasheva, E. S. Ivanova, S. A. Smolyaninova, K. P. Pashchenko, A. I. Poddel′sky, and N. T. Berberova. Catechol- and phenol-containing thio-schiff bases: Synthesis, electrochemical properties and biological evaluation. ChemistrySelect, 2021, 6, 10609-10618. https://doi.org/10.1002/slct.202102246
M. A. Zherebtsov, M. V. Arseniev, N. M. Khamaletdinova, E. V. Baranov, and S. A. Chesnokov. Di-tret-alkilzameshchennye pirokatekhiny s imidazol′nym zamestitelem: sintez, stroenie i svoistva (Di-tert-alkyl-substituted pyrocatechins with an imidazole substituent: synthesis, structure and properties). Izv. Akad. Nauk, Ser. Khim., 2023, (9), 2102-2118. [In Russian]
S. Wu, D. Zhou, F. Geng, J. Dong, L. Su, Y. Zhou, and S.-F. Yin. Metal-free oxidative condensation of catechols, aldehydes and NH4OAc towards benzoxazoles. Adv. Synth. Catal., 2021, 363, 3607-3614. https://doi.org/10.1002/adsc.202100249
H. Ke, W. Wei, Y. Yang, H. Wu, Y.-Q. Zhang, G. Xie, and S. Chen. A trinuclear zinc coordination cluster exhibitting fluorescence, colorimetric sensitivity, and recycling of silver ion and detection of cupric ion. Inorg. Chem., 2020, 59, 2833-2842. https://doi.org/10.1021/acs.inorgchem.9b03169
I. V. Smolyaninov, V. V. Kuzmin, M. V. Arsenyev, S. A. Smolyaninova, A. I. Poddel′sky, and N. T. Berberova. Electrochemical transformations and anti/prooxidant activity of sterically hindered o-benzoquinones. Russ. Chem. Bull., 2017, 66, 1217-1229. https://doi.org/10.1007/s11172-017-1876-7
M. P. Shurygina, M. Y. Zakharina, M. A. Baten′kin, A. N. Konev, A. S. Shavyrin, E. A. Chelnokov, N. Y. Shushunova, M. V. Arsenyev, S. A. Chesnokov, and G. A. Abakumov. A blue to red light sensitive photoinitiating systems based on 3,5-di-tert-butyl-o-benzoquinone derivatives for free radical polymerization. Eur. Polym. J., 2020, 127, 109573. https://doi.org/10.1016/j.eurpolymj.2020.109573
S. S. Batsanov. The atomic radii of the elements. Russ. J. Inorg. Chem., 1991, 36(12), 1694-1706.
P. M. Zorky and Yu. V. Zefirov. New applications of van der Waals radii in chemistry. Russ. Chem. Rev., 1995, 64, 415-428. https://doi.org/10.1070/RC1995v064n05ABEH000157
S. N. Brown. Metrical oxidation states of 2-amidophenoxide and catecholate ligands: structural signatures of metal–ligand π bonding in potentially noninnocent ligands. Inorg. Chem., 2012, 51, 1251-1260. https://doi.org/10.1021/ic202764j
E. Ruiz, A. Rodrı́guez-Fortea, P. Alemany, and S. Alvarez. Density functional study of the exchange coupling in distorted cubane complexes containing the Cu4O4 core. Polyhedron, 2001, 20, 1323-1327. https://doi.org/10.1016/S0277-5387(01)00613-1
A. W. Addison, T. N. Rao, J. Reedijk, J. van Rijn, and G. C. Verschoor. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II) perchlorate. Dalton Trans., 1984, 7, 1349-1356. https://doi.org/10.1039/DT9840001349
Funding
The research was carried out at IOMC RAS using the of equipment the Analytical Center of IOMC RAS funded by the grant “Scientific Equipment for the Development of the Material and Technical Infrastructure of Common Use Centers” (unique identifier RF-2296.61321X0017, Agreement No. 075-15-2021-670).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interests.
Additional information
Russian Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 11, 117710.https://doi.org/10.26902/JSC_id117710
Rights and permissions
About this article
Cite this article
Zherebtsov, M.A., Arsenyev, M.V., Baranov, E.V. et al. Synthesis and Structure of an o-Quinone Based Cuban Copper Complex with a Benzoxazole Substituent. J Struct Chem 64, 2051–2062 (2023). https://doi.org/10.1134/S0022476623110033
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476623110033