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DOI: 10.1055/a-2644-2148
Synthesis of Novel Guanidine-Schiff-Base Iron(III) and Zinc(II) Complexes
Authors
Supported by: European Commission 953073
Funding Information We thank the European Commission for funding under Horizon 2020 Grant Agreement no. 953073 (UPLIFT project).
Dedication
Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.
Abstract
Hybrid guanidine ligands and their metal complexes are an important field of research due to their diverse applications and highly modular structure. In this work, the synthesis of four bench-stable iron(III) and zinc(II) complexes of two novel tridentate guanidine-Schiff-base ligands is presented. Although the ligands themselves were found to be unstable, the preparation of the stable metal complexes could be conducted on a gram scale and in high yields (≥88%) without isolation of the corresponding unstable ligand. All complexes were characterized by single-crystal X-ray diffraction, and their structural features are discussed.
Primary Data
Crystallographic data for complexes C1–C4 have been deposited at the Cambridge Crystallographic Data Centre (CCDC) as supplementary no. CCDC – 2452469 for C1, CCDC – 2452470 for C2, CCDC – 2452471 for C3, and CCDC – 2452472 for C4. Additional information on the synthesis and characterization of the presented new compounds is available via the Chemotion Repository. The respective links are given at the end of the experimental procedures.
Publication History
Received: 29 May 2025
Accepted after revision: 26 June 2025
Accepted Manuscript online:
26 June 2025
Article published online:
13 August 2025
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References
- 1a Stanek J, Rösener T, Metz A, Mannsperger J, Hoffmann A, Dr. Herres-Pawlis S. Selig P. ed Guanidines as Reagents and Catalysts II. Vol 51. Cham: Springer; 2015: 95
- 1b Laurini L, Conte SM, Hüser K. et al. Eur J Inorg Chem 2024; 27: e202300700
- 2a Lohmeyer L, Kaifer E, Himmel H-J. Inorg Chem 2022; 61: 8440
- 2b Holzmann SL, Osterbrink J, Hübner O. et al. Eur J Inorg Chem 2025; 28: e202400597
- 3 Kröckert KW, Garg F, Heck J. et al. Dalton Trans 2024; 53: 2973
- 4a Li M, Cai Z, Eisen MS. J Catal 2023; 420: 58
- 4b Li M, Cai Z, Eisen MS. Inorg Chem 2024; 63: 1774
- 4c Li M, Eisen MS, Cai Z. J Catal 2024; 435: 115581
- 5a Rittinghaus RD, Schäfer PM, Albrecht P. et al. ChemSusChem 2019; 12: 2161
- 5b Schäfer PM, Herres-Pawlis S. ChemPlusChem 2020; 85: 1044
- 5c Conrads C, Burkart L, Soerensen S. et al. Catal Sci Technol 2023; 13: 6006
- 6a Fuchs M, Schäfer PM, Wagner W. et al. ChemSusChem 2023; 16: e202300192
- 6b Burkart L, Eith A, Hoffmann A, Herres-Pawlis S. Chem Asian J 2023; 18: e202201195
- 6c Becker T, Hermann A, Saritas N, Hoffmann A, Herres-Pawlis S. ChemSusChem 2024; 17: e202400933
- 7a Kawahata M, Yamaguchi K, Ito T, Ishikawa T. Acta Crystallogr, Sect E: Crystallogr Commun 2006; 62: o3301
- 7b Herres-Pawlis S, Neuba A, Seewald O. et al. Eur J Org Chem 2005; 2005: 4879
- 8 Paul M, Teubner M, Grimm-Lebsanft B. et al. Chem Eur J 2020; 26: 7556
- 9 Hoffmann A, Börner J, Flörke U, Herres-Pawlis S. Inorg Chim Acta 2009; 362: 1185
- 10 Hermann A, Becker T, Schäfer MA, Hoffmann A, Herres-Pawlis S. ChemSusChem 2022; 15: e202201075
- 11 Schäfer PM, McKeown P, Fuchs M. et al. Dalton Trans 2019; 48: 6071
- 12a Cozzi PG. Chem Soc Rev 2004; 33: 410
- 12b Gibson VC, Redshaw C, Solan GA. Chem Rev 2007; 107: 1745
- 13 Kawahata M, Yamaguchi K, Ishikawa T. Cryst Growth Des 2005; 5: 373
- 14a Ohno K, Ishida W, Kamata K. Heterocycles 2003; 59: 317
- 14b El-Faham A, Chebbo M, Abdul-Ghani M, Younes G. J Heterocycl Chem 2006; 43: 599
- 15 Rittinghaus RD. Iron Guanidine Complexes as Polymerization Catalysts for ROP and ATRP. PhD Thesis Aachen, Germany: RWTH Aachen University; 2021
- 16a Bienemann O. Kupfer- Und Eisen-Guanidinkomplexe für Die Atomtransfer-Radikalpolymerisation. PhD thesis Dortmund, Germany: Technische Universität Dortmund; 2013
- 16b Rittinghaus RD, Karabulut A, Hoffmann A, Herres-Pawlis S. Angew Chem Int Ed 2021; 60: 21795
- 17 Wortmann R. Mangan- Und Eisen-Guanidin-Komplexe Und Ihre Anwendung Als Katalysatoren in der Alkenepoxidierung. PhD Thesis Paderborn, Germany: Universität Paderborn; 2011
- 18 Steuer L, Kaifer E, Himmel H-J. Dalton Trans 2021; 50: 9467
- 19a Alvarez S, Avnir D, Llunell M, Pinsky M. New J Chem 2002; 26: 996
- 19b Llunell M, Casanova D, Cirera J, Alemany P, Alvarez S. SHAPE, Version 2.1. 2013
- 20 Peris E, Crabtree RH. Chem Soc Rev 2018; 47: 1959
- 21 Addison AW, Rao TN, Reedijk J, van Rijn J, Verschoor GCJ. Chem Soc, Dalton Trans 1984; 1349
- 22 Hubschle CB, Sheldrick GM, Dittrich B. J Appl Crystallogr 2011; 44: 1281
- 23 Raab V, Harms K, Sundermeyer J, Kovačević B, Maksić ZB. J Org Chem 2003; 68: 8790
- 24a Kantlehner W, Haug E, Mergen WW. et al. Liebigs Ann Chem 1984; 1984: 108
- 24b Wittmann H, Raab V, Schorm A, Plackmeyer J, Sundermeyer J. Eur J Inorg Chem 2001; 2001: 1937
- 24c Raab V, Kipke J, Gschwind RM, Sundermeyer J. Chem Eur J 2002; 8: 1682
- 24d Herres-Pawlis S, Flörke U, Henkel G. Eur J Inorg Chem 2005; 2005: 3815
- 25 Huang Y-C, Tremouilhac P, Nguyen A, Jung N, Bräse SJ. Cheminformatics 2021; 13: 8
- 26 Gottlieb HE, Kotlyar V, Nudelman A. J Org Chem 1997; 62: 7512
- 27 STOE X-Area Pilatus3_SV Version 1.31.170.0. Darmstadt, Germany: STOE & Cie GmbH; 2020
- 28 STOE X-Area Integrate Version 1.78.3.0. Darmstadt, Germany: STOE & Cie GmbH; 2020
- 29 STOE X-Area Recipe Version 1.36.0.0. Darmstadt, Germany: STOE & Cie GmbH; 2020
- 30 STOE X-Area LANA Version 1.83.8.0. Darmstadt, Germany: STOE & Cie GmbH; 2020
- 31 Bruker XPREP. Madison, WI, USA: Bruker AXS Inc.; 2007
- 32 Sheldrick G. Acta Crystallogr, Sect A 2015; 71: 3
- 33 Sheldrick G. Acta Crystallogr, Sect C 2015; 71: 3