Abstract
2,2-Bis[2-(dimethylamino)-5-methylphenyl]acetic acid, Ar2CHCOOH (1) (Ar = 5-Me-2-Me2NC6H3), was synthesized by the carboxylation of s[2-(dimethylamino)-5-methylphenyl]-methyllithium, [Ar2CH]Li(TMEDA), with gaseous CO2. The reaction of 1 with the cationic bis(alkyl) complex [(Me3SiCH2)2Dy(THF)n][BPh4] (2: 1 molar ratio) unexpectedly afforded the tetracarboxylate complex [Dy(O2CCHAr2)4(Et2NH2)2][BPh4] (3), whereas the trinuclear oxo cluster [Dy3O(O2CHAr2)6(THF)4][BPh4] (4) was prepared from [(o-Me2NC6H4CH2)2-Dy(THF)n][BPh4]. In complex 4, three Dy3+ cations are linked by the μ3-oxo oxygen atom and six bridging μ2-κ1-O:κ1-O’-carboxylate ligands. According to the X-ray diffraction data, NMe2 groups of the diphenylmethanide moiety are not coordinated to Dy3+ cations in complexes 3 and 4.
Similar content being viewed by others
References
R. Janicki, A. Mondry, P. Starynowicz, Coord. Chem. Rev., 2017, 340, 98.
L. Ding, L.-H. Liu, Q. Shi, Y.-Q. Sun, Y.-J. Wang, Y.-P. Chen, Inorg. Chem., 2017, 56, 14850.
B. Casanovas, S. Speed, M. S. El Fallah, R. Vicente, M. Font-Bardía, F. Zinna, L. Di Bari, Dalton Trans., 2019, 48, 2059.
M. Kumar, L.-H. Wu, M. Kariem, A. Franconetti, H. N. Sheikh, S.-J. Liu, S. C. Sahoo, A. Frontera, Inorg. Chem., 2019, 58, 7760.
B. Fernández, I. Oyarzabal, E. Fischer-Fodor, S. Macavei, I. Sánchez, J. M. Seco, S. Gómez-Ruiz, A. Rodríguez-Diéguez, CrystEngComm, 2016, 18, 8718.
Q. Zhang, J. Wang, A. M. Kirillov, W. Dou, C. Xu, C. Xu, L. Yang, R. Fang, W. Liu, ACS Appl. Mater. Interfaces, 2018, 10, 23976.
D. N. Woodruff, R. E. P. Winpenny, R. A. Layfield, Chem. Rev., 2013, 113, 5110.
M. A. Shmelev, Yu. K. Voronina, N. V. Gogoleva, A. A. Sidorov, M. A. Kiskin, F. M. Dolgushin, Yu. V. Nelyubina, G. G. Aleksandrov, E. A. Varaksina, I. V. Taydakov, I. L. Eremenko, Russ. Chem. Bull., 2020, 69, 1544.
T. S. Sukhikh, D. S. Ogienko, D. A. Bashirov, S. N. Konchenko, Russ. Chem. Bull., 2019, 68, 651.
Y.-Z. Zheng, G.-J. Zhou, Z. Zheng, R. E. P. Winpenny, Chem. Soc. Rev., 2014, 43, 1462.
K. Liu, W. Shi, P. Cheng, Coord. Chem. Rev., 2015, 289–290, 74.
J.-L. Liu, Y.-C. Chen, F.-S. Guo, M.-L. Tong, Coord. Chem. Rev., 2014, 281, 26.
M. Guo, Y. Xu, J. Wu, L. Zhao, J. Tang, Dalton Trans., 2017, 46, 8252.
H. Tian, J.-B. Su, S.-S. Bao, M. Kurmoo, X.-D. Huang, Y.-Q. Zhang, L.-M. Zheng, Chem. Sci., 2018, 9, 6424.
N. N. Efimov, P. S. Koroteev, A. V. Gavrikov, A. B. Ilyukhin, Z. V. Dobrokhotova, V. M. Novotortsev, Magnetochemistry, 2016, 2, 38.
O. Khalfaoui, A. Beghidja, J. Long, A. Boussadia, C. Beghidja, Y. Guari, J. Larionova, Dalton Trans., 2017, 46, 3943.
B. S. Sran, J. F. Gonzalez, V. Montigaud, B. Le Guennic, F. Pointillart, O. Cador, G. Hundal, Dalton Trans., 2019, 48, 3922.
G.-J. Zhou, Y.-S. Dinga, Y.-Z. Zheng, Dalton Trans., 2017, 46, 3100.
S. Biswas, L. Mandal, Y. Shen, M. Yamashita, Dalton Trans., 2019, 48, 14096.
W. J. Evans, D. G. Giarikos, G. Dimitrios, W. Joseph, Organometallics, 2001, 20, 5751.
A. Fishbach, F. Perdih, E. Herdtweck, R. Anwander, Organometallics, 2006, 25, 1626.
R. Sen, D. Saha, S. Koner, Catal. Lett., 2012, 142, 124.
H. T. D. Nguyen, Y. B. N. Tran, H. N. Nguyen, T. C. Nguyen, F. Gándara, P. T. K. Nguyen, Inorg. Chem., 2018, 57, 13772.
W. J. Evans, D. G. Giarikos, Macromolecules, 2004, 37, 5130.
R. Sen, D. K. Hazra, S. Koner, M. Helliwell, M. Mukherjee, A. Bhattacharjee, Polyhedron, 2010, 29, 3183.
A. Fischbach, F. Perdih, P. Sirsch, W. Scherer, R. Anwander, Organometallics, 2002, 21, 4569.
Z. Zhang, D. Cui, B. Wang, B. Liu, Y. Yang, Struct. Bond., 2010, 137, 49.
R. A. Coxall, S. G. Harris, D. K. Henderson, S. Parsons, P. A. Tasker, R. E. P. Winpenny, J. Chem. Soc., Dalton Trans., 2000, 2349.
Rare Earth Coordination Chemistry: Fundamentals and Applications, Ed. Ch. Huang, John Wiley & Sons (Asia), Pte Ltd, 2010.
M.-F. Wu, M.-S. Wang, S.-P. Guo, F.-K. Zheng, H.-F. Chen, X.-M. Jiang, G.-N. Liu, G.-C. Guo, J.-S. Huang, Cryst. Growth Des., 2011, 11, 372.
N. Xu, W. Shi, D.-Z. Liao, S.-P. Yan, P. Cheng, Inorg. Chem., 2008, 47, 8748.
C.-S. Liu, M. Du, E. C. Sañudo, J. Echeverria, M. Hu, Q. Zhang, L.-M. Zhou, S.-M. Fang, Dalton Trans., 2011, 40, 9366.
J. Leciejewicz, H. Ptasiewicz-Bąk, T. Premkumar, S. Govindarajan, J. Coord. Chem., 2004, 57, 97.
D. O. Khristolyubov, D. M. Lyubov, A. V. Cherkasov, G. K. Fukin, A. S. Shavyrin, A. A. Trifonov, Organometallics, 2018, 37, 1627.
D. O. Khristolyubov, D. M. Lyubov, A. S. Shavyrin, A. V. Cherkasov, G. K. Fukin, A. A. Trifonov, Inorg. Chem. Front., 2020, 7, 2459.
D. O. Khristolyubov, D. M. Lyubov, A. V. Cherkasov, G. K. Fukin, A. A. Trifonov, Mendeleev Commun., 2021, 31, 54.
J. W. Sharples, Y.-Z. Zheng, F. Tuna, E. J. L. McInnes, D. Collison, Chem. Commun., 2011, 47, 7650.
D. M. Roitershtein, A. A. Vinogradov, K. A. Lyssenko, I. V. Ananyev, V. A. Yakovlev, N. N. Kostitsyna, I. E. Nifant’ev, Inorg. Chim. Acta, 2018, 487, 153.
D. M. Roitershtein, A. A. Vinogradov, K. A. Lyssenko, I. E. Nifant’ev, Inorg. Chem. Commun., 2017, 84, 225.
D. M. Roitershtein, A. A. Vinogradov, A. A. Vinogradov, K. A. Lyssenko, Y. V. Nelyubina, I. V. Ananyev, I. E. Nifantev, V. A. Yakovlev, N. N. Kostitsyna, Organometallics, 2013, 32, 1272.
M. E. Minyaev, A. A. Vinogradov, D. M. Roitershtein, K. A. Lyssenko, I. V. Ananyev, I. E. Nifant’ev, Acta Crystallogr., Sect. C: Cryst Struct. Chem., 2016, 72, 578.
M. Ramos Silva, C. Cardoso, A. Matos Beja, J. A. Paixão, S. R. Domingos, J. Chem. Crystallogr., 2008, 38, 403.
S. Hovmöller, R. Norrestam, T.-B. Palm, Acta Cryst., 1997, B33, 377.
Z.-L. Wang, W.-H. Fanga, G.-Y. Yang, Chem. Commun., 2010, 46, 8216.
Y. Song, B. Yan, Z. Chen, J. Coord. Chem., 2005, 58, 647.
L. F. Marques, A. A. B. Cantaruti J, C. C. Correa, M. G. Lahoud, R. R. da Silva, S. J. L. Ribeiro, F. C. Machado, J. Photochem. Photobiol. A: Chem., 2013, 252, 69.
Y. Zhang, M. Bhadbhade, N. Scales, I. Karatchevtseva, J. R. Price, K. Lu, G. R. Lumpkin, J. Solid. State Chem., 2014, 219, 1.
E. Echenique-Errandonea, I. Oyarzabal, J. Cepeda, E. San Sebastian, A. Rodríguez-Diéguez, J. M. Seco, New. J. Chem., 2017, 41, 5467.
O. Khalfaoui, A. Beghidja, J. Long, C. Beghidja, Y. Guari, J. Larionova, Inorganics, 2018, 6, 35.
H.-R. Wen, X.-R. Xie, S.-J. Liu, J. Bao, F.-F. Wang, C.-M. Liu, J.-S. Liao, RSC Advances, 2015, 5, 98097.
Y.-Z. Zheng, M. Evangelisti, R. E. P. Winpenny, Angew. Chem., Int. Ed., 2011, 50, 3692.
S. R. Kiraev, S. A. Nikolaevskii, M. A. Kiskin, I. V. Ananyev, E. A. Varaksina, I. V. Taydakov, G. G. Aleksandrov, A. S. Goloveshkin, A. A. Sidorov, K. A. Lyssenko, I. L. Eremenko, Inorg. Chim. Acta., 2018, 477, 15.
N. S. Hosmane, Y. Wang, A. R. Oki, H. Zhang, J. A. Maguire, Organometallics, 1996, 15, 626.
K. C. Hultzsch, P. Voth, K. Beckerle, T. P. Spaniol, J. Okuda, Organometallics, 2000, 19, 228.
S. Arndt, P. Voth, T. P. Spaniol, J. Okuda, Organometallics, 2000, 19, 4690.
S. Bambirra, M. W. Bouwkamp, A. Meetsma, B. Hessen, J. Am. Chem. Soc., 2004, 126, 9182.
S. Harder, C. Ruspic, N. N. Bhriain, F. Berkermann, M. Schurmann, Z. Naturforsch., B: Chem. Sci., 2008, 63, 267.
S. J. Lyle, M. M. Rahman, Talanta, 1953, 10, 1177.
Bruker (2015). APEX3, Bruker AXS Inc., Madison, Wisconsin, USA.
Rigaku Oxford Diffraction. CrysAlisPro, ver. 1.171.38.46, Rigaku Corporation, Wroclaw, Poland, 2015.
L. Krause, R. Herbst-Irmer, G. M. Sheldrick, D. Stalke, J. Appl. Cryst., 2015, 48, 3.
G. M. Sheldrick, Acta Cryst., 2015, C71, 3.
A.L. Spek, Acta Cryst., 2015, C71, 9.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 818–829, May, 2021.
This work was financially supported by the Russian Science Foundation (Project No. 17-73-30036). The X-ray diffraction study was performed within the framework of the state assignment using equipment of the Joint Analytical Center of the G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences.
No human or animal subjects were involved in this research.
The authors declare no conflict of interest, financial or otherwise.
Rights and permissions
About this article
Cite this article
Khristolyubov, D.O., Lyubov, D.M., Makhrova, T.V. et al. Synthesis and structure of DyIII 2,2-bis[2-(dimethylamino)-5-methylphenyl]acetate complexes. Russ Chem Bull 70, 818–829 (2021). https://doi.org/10.1007/s11172-021-3155-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-021-3155-x