Abstract
This review includes 70 monomeric high-spin complexes of the following general compositions: [Fe(II)(η3-pdc)(L)3], [Fe(III)(η3-pdc)(L)3]+, [Fe(II)(η3-pdc)2]2− and [Fe(III)(η3-pdc)2]− (pdc = pyridine-2,6-dicarboxylate (−2)). Each Fe(II) atom has a distorted octahedral geometry. The Fe(III) atoms have a distorted octahedral geometry (most common) and in some examples have a distorted pentagonal-bipyramidal geometry. The chelating donor ligands create varieties of n-membered metallocyclic rings: ONO, OCO, NC2N, OC2N, OC2NO and OC3O. Some cooperative effects between Fe(II) and Fe(III) complexes were found and discussed. There are complexes that are examples of distortion isomerism.
Acknowledgments
The authors would like to thank the grant agency of the Slovak Republic (APVV-18-0016, Funder Id: http://dx.doi.org/10.13039/501100003194) for their financial support. This article was created with the support of the MŠVVaŠ of the Slovak Republic within the Research and Development Operation Program for the project “University Science Park of STU Bratislava” (ITMS project no. 26240220084, Funder Id: http://dx.doi.org/10.13039/501100003194) cofounded by the European Regional Development Fund.
References
Abboud, K.A.; Hu, Ch.; Drago, R. Triaqua(pyridine-2,6-dipicolinato-O,N,O′)iron(III) bis(pyridine-2,6-dipicolinato-O,N,O′)iron(III) hexahydrate: an unusual ion-pair compound. Acta Crystallogr., Sect. C, Cryst. Struct. Commun.1998, 54, 1270–1273.10.1107/S0108270198000183Search in Google Scholar
Adolf, C.R.R.; Ferlay, S.; Kyritsakas, N.; Hosseini, M.W. Welding molecular crystals. J. Am. Chem. Soc.2015, 137, 15390–15393.10.1021/jacs.5b10586Search in Google Scholar PubMed
Aghabozorg, H.; Nemati, A.; Derikvand, D.; Ghadermazi, M. Piperazinediium bis[bis(pyridine-2,6-dicarboxylato)ferrate(III)] monohydrate. Acta Crystallogr. Sect. E., Struct. Rep. Online2007a, 63, m2921.10.1107/S1600536807055468Search in Google Scholar
Aghabozorg, H.; Sadrkhanlou, E.; Soleimannejad, J.; Adams, H. 2,9-Dimethyl-1,10-phenanthrolinium bis(pyridine-2,6-dicarboxylato-κ3O,N,O′)ferrate(III) dehydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2007b, 63, m1760.10.1107/S1600536807025081Search in Google Scholar
Aghabozorg, H.; Panah, F.M.; Sadr-Khanlou, E. Crystal structure of [Fe(bpy)3][Fe(pydc)2]2(pydcH2) 1/2 ·6.5H2O complex (bpy=2,2′-bipyridine, pydc=pyridine-2,6-dicarboxylate). Anal. Sci., X-ray Struct. Anal. Online2007c, 23, 139.10.2116/analscix.23.x139Search in Google Scholar
Ahadiat, G.; Tabatabase, M.; Gholivand, K.; Buzek, M. Structure of diaqua-(nitrato)-(pyridine-2,6-dicarboxylato)-iron dehydrate. CSD Communication (Private Communication) CCDC UYAQUI 2016.Search in Google Scholar
Ansari, I.A.; Sama, F.; Shahio, M.; Arif, R.R.; Khalid, M.; Siddiqi, Z.A.S. Isolation of proton transfer complexes containing 4-picolinium as cation and pyridine-2,6-dicarboxylate complex as anion: crystallographic and spectral investigations, antioxidant activities and molecular docking studies. RSC Adv.2016, 6, 11088–11098.10.1039/C5RA25939HSearch in Google Scholar
Anwar, M.U.; Dawe, L.N.; Parsons, S.R.; Tandon, S.S.; Thompson, L.K.; Subrata, K.D.; Mereacre, S.K.; Reiff, W.M. Oligonuclear Fe complexes (Fe, Fe4, Fe6, Fe9) derived from tritopic pyridine bis-hydrazone ligands – structural, magnetic, and Mössbauer studies. Inorg. Chem.2014, 53, 4655–4668.10.1021/ic500348kSearch in Google Scholar PubMed
Cousson, A.; Nectoux, F.; Rizkalla, E.N. Structure of bis(dipicolinato)ferrate(III) dehydrate. Acta Crystallogr., Sect. C, Cryst. Struct. Commun.1992, 48, 1354–1357.10.1107/S0108270192002877Search in Google Scholar
Cousson, A.; Nectour, E.; Robert, F.; Rizkalla, E.N. Sodium bis(dipicolinato)ferrate(III) dihydrate. Acta Crystallogr., Sect. C, Cryst. Struct. Commun.1995, 51, 838–840.10.1107/S0108270194005561Search in Google Scholar
Derikvand, Z.; Nemati, A.; Shokrollahi, A.; Zarghampour, F. Synthesis, characterization, spectroscopic, crystal structures and solution studies of two coordination compounds of zinc(II) and iron(III) based on chelidamic acid and acridine. Inorg. Chim. Acta2012, 392, 362–373.10.1016/j.ica.2012.03.034Search in Google Scholar
Eshtiagh-Hosseini, H.; Yousefi, Z.; Shafiee, M.; Mizzali, M. Fe(III) and cobalt(II) coordination compounds of 5-bromo-6-methyl-2-morpholinepyrimidinium-4-amine pyridine-2,6-dicarboxylate. J. Coord. Chem.2010, 63, 3187–3197.10.1080/00958972.2010.508284Search in Google Scholar
Eshtiagh-Hosseini, H.; Mirzaei, M.; Yousefi, Z.; Puschmann, H.; Shokrollahi, A.; Aghaei, R. Structural aspects and solution behavior of metallosupramolecular compound of FeIII ion obtained by proton transfer. J. Coord. Chem.2011, 64, 3969–3979.10.1080/00958972.2011.634907Search in Google Scholar
Gao, H.L.; Zhang, H.; Kang, H.P.; Cui, J.Z. Synthesis and crystal structure of a complex derived from iron(Ⅲ) and two kinds of 4-hydroxypyridine dicarboxylic acid. Wuji Huaxue Xuebao (Chin.), Chem. J. Inorg. Chem.2007, 23, 1099–1102.Search in Google Scholar
Ghasemi, F.; Ghasemi, K.; Rezmani, A.R.; Rosli, M.M.; Razak, I.A. Synthesis, characterization, crystal structure and electrochemical studies of ionic iron(III) dipicolinato complex. J. Mol. Struct.2017, 1144, 186–190.10.1016/j.molstruc.2017.05.044Search in Google Scholar
Han, D.; Wang, D. Aqua(picolinato N-oxide-κ2O1,O2)(pyridine-2,6-dicarboxylato-κ3O,N,O′)iron(III) monohydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2008, 64, m1343.10.1107/S1600536808030663Search in Google Scholar
Hernandez-Anzaldo, S.; Sanchez-Morales, N.; Zamoralo-Ulloa, R.; Escudero, R.; de Hoz, M.J.R.; Reyer-Ortega, Y. J. Mol. Struct.2013, 1040, 39–46.10.1016/j.molstruc.2013.02.021Search in Google Scholar
Hernandez-Anzaldo, S.; Sanchez-Morales, N.; Alcantara-Flores, J.L.; Guturreez-Perez, R.; Zamorane-Ulloas, R.; Esecadero, R.; de Hoz, M.J.H.; Reyez-Ortega, Y. Structure of aqua-chloro-(dimethyl sulfoxide-O)-(pyridine-2,6-dicarboxylato-N,O,O′)-iron(III). CSD Communication (Private communication), CCDC, IDOJIV 2014.Search in Google Scholar
Hou, Z.Y.; Zhu, D.M. 1,1′-(Butane-1,4-diyl)bis(1H-benzimidazol-3-ium) bis[bis(pyridine-2,6-dicarboxylato-κ3O,N,O′)ferrate(III)] methanol disolvate. Acta Crystallogr., Sect. E, Struct. Rep. Online2006, 62, m1–m3.10.1107/S1600536805039152Search in Google Scholar
Hseu, J.F.; Chen, J.J.; Chuang, C.C.; Wei, H.H.; Cheng, M.C.; Wang, Y.; Yao, Y.O. Crystal structure, magnetic property and Mössbauer spectra of bis(pyridine-2,6-dicarboxylato) iron(III) dehydrate. Inorg. Chim. Acta1991, 184, 1–5.10.1016/S0020-1693(00)83037-6Search in Google Scholar
Hu, X.; Guo, J.; Wang, Y.; Liu, C. Synthesis, infrared spectra, thermal analyses and structural studies of half-sandwich Fe(III)/Fe(II) complex containing pyridine-2,6-dicarboxylate and 1,10-phenanthroline. Spectrochim. Acta, Part A2009, 74, 48–51.10.1016/j.saa.2009.04.027Search in Google Scholar PubMed
Ilkimen, H.; Yenikaya, C.; Sari, M.; Bulbul, M.; Tunca, E.; Suzen, Y. Synthesis and characterization of a proton transfer salt between dipicolinic acid and 2-amino-6-methylbenzothiazole and its complexes, and their inhibition studies on carbonic anhydrase isoenzymes. Polyhedron2013, 61, 56–64.10.1016/j.poly.2013.05.040Search in Google Scholar
Ilkimen, H.; Yenikaya, C.; Sari, M.; Bulbul, M.; Tunca, E.; Dal, H.; Bas, M. Synthesis and characterization of a proton transfer salt between 2,6-pyridinedicarboxylic acid and 2-aminobenzothiazole, and its complexes and their inhibition studies on carbonic anhydrase isoenzymes. J. Enzyme Inhib. Med. Chem.2014, 29, 353–361.10.3109/14756366.2013.782299Search in Google Scholar PubMed
Ilkimen, H.; Yenikaya, C.; Sari, M.; Bulbul, M.; Tunca, E.; Dal, H.; Bas, M. Synthesis and characterization of complexes of a novel proton transfer salt and their inhibition studies on carbonic anhydrase isoenzymes. J. Enzyme Inhib. Med. Chem.2015, 30, 195–203.10.3109/14756366.2014.908290Search in Google Scholar
Jain, S.L.; Slawin, A.M.Z.; J. Woollins, D.; Bhattacharyya, P. The reactions of elemental iron with dipicolinic acid (H2dipic) and quinaldic acid (Hquin)-X-ray crystal structures of [C5H5NH][Fe(Dipic)(Hdipic)(C5H5N)2]·3C5H5N, [Fe2(μ-O)(Dipic)2(C5H5N)4]·2C5H5N·2H2O and trans-[Fe(Quin)2(MeOH)2]. Eur. J. Inorg. Chem.2005, 721–726. DOI:10.1002/ejic.200400728.10.1002/ejic.200400728Search in Google Scholar
Koman, M.; Melník, M.; Uhrecký, R.; Moncol, J. Crystal structures and Hirshfeld surface analysis of (cat)2[FeIII(η3-dipic)(NCS)3] and (cat)[FeIII(η3-dipic)(H2O)(NCS)2] (dipic=dipicolinate). Polyhedron.2020, 183, 114529.10.1016/j.poly.2020.114529Search in Google Scholar
Laine, P.; Gourdon, A.; Launay, J.P. Chemistry of iron with dipicolinic acid. 4. mixed-ligand complexes of iron(III) and related compounds. Inorg. Chem.1995a, 34, 5129–5137.10.1021/ic00125a012Search in Google Scholar
Laine, P.; Gourdon, A.; Launay, J.P. Chemistry of iron with dipicolinic acid. 1. Mononuclear complexes of iron(II) or iron(III). Inorg. Chem.1995b, 34, 5156–5165.10.1021/ic00125a009Search in Google Scholar
Laine, P.; Gourdon, A.; Launay, J.P. Chemistry of iron with dipicolinic acid. 2. Bridging role of carboxylate groups in solid state structures. Inorg. Chem.1995c, 34, 5138–5149.10.1021/ic00125a010Search in Google Scholar
Marsh, R.E. On the crystal structure of bis-(dipicolinato)ferrate(III) dehydrate. Acta Crystallogr., Sect. C, Cryst. Struct. Commun.1993, 49, 643.10.1107/S0108270192011673Search in Google Scholar
Melník, M. Structural isomerism of copper(II) compounds. Coord. Chem. Rev.1982, 47, 239–261.10.1016/0010-8545(82)85033-9Search in Google Scholar
Melník, M.; Sharrock, P. Seven coordination in molybdenum chemistry: analysis of oligonuclear structures. Coord. Chem. Rev.1985, 65, 49–85.10.1016/0010-8545(85)85021-9Search in Google Scholar
Melník, M.; Ondrejkovičová, I.; Vančová, V.; Holloway, C.E. Structural aspects of iron coordination componds: I. Monomeric derivatives. Rev. Inorg. Chem. 1997, 17, 55–286.10.1515/REVIC.1997.17.2-3.55Search in Google Scholar
Mirzaei, M.; Eshtiagh-Hosseini, H.; Eydizadeh, E.; Yousefi, Z.; Molcanov, K. 9-Aminoacridinium bis(pyridine-2,6-dicarboxylato-κ3O2,N,O6)ferrate(III) tetrahydrate. Acta Crystallogr. Sect. E, Struct. Rep. Online2012a, 68, m761–m762.10.1107/S1600536812020247Search in Google Scholar PubMed PubMed Central
Mirzaei, M.; Eshtiagh-Hosseini, H.; Mague, J.T. 2-Aminopyridinium bis(pyridine-2,6-dicarboxylato)ferrate(III). Acta Crystallogr., Sect. E, Struct. Rep. Online2012b, 68, m174.10.1107/S1600536812001493Search in Google Scholar PubMed PubMed Central
Mirzaei, M.; Esthiagh-Hosseini, H.; Shamsipur, M.; Saeedi, M.; Ardalani, M.; Bauza, A.; Mague, J.T.; Frontera, A.; Habibi, M. Importance of polarization assisted/resonance assisted hydrogen bonding interactions and unconventional interactions in crystal formations of five new complexes bearing chelidamic acid through a proton transfer mechanism. RSC Adv2015, 5, 72923–72936.10.1039/C5RA09526CSearch in Google Scholar
Mirzaei, M. Structure of 2-aminopyrimidinium bis(pyridine-2,6-dicarboxylato)-iron(III) dehydrate. CSD Communication (Private Communication) CCDC, IZUSIH, 2016.Search in Google Scholar
Qi-Hua, Z.; Zhang, M.S.; Fang, R.B. 2-(2-Pyridyl)pyridinium bis(pyridine-2,6-dicarboxylato-κ2O2,O6)iron(III) trihydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2005, 61, m2575–m2577.10.1107/S1600536805036469Search in Google Scholar
Rafizadeh, M.; Mehrabi, B.; Amani, V. Aquachloro(dimethyl sulfoxide-κO)(pyridine-2,6-dicarboxylato-κ3O,N,O′)iron(III). Acta Crystallogr.Sect E, Struct. Rep. Online2006, 62, m1332–m1334.10.1107/S1600536806017387Search in Google Scholar
Rafizadeh, M.; Derikvand, Z.; Nemati, A. 2,6-Diaminopyridinium bis(4-hydroxypyridine-2,6-dicarboxylato-κ3O2,N,O6)ferrate(III) dehydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2008, 64, m1300–m1301.10.1107/S1600536808029280Search in Google Scholar PubMed PubMed Central
Singh, M.P.; Baruah, J.B. Stable host–guest complexes of bis-2,6-pyridinedicarboxylate iron(III) with dihydroxybenzenes. Polyhedron2017, 138, 103–108.10.1016/j.poly.2017.09.013Search in Google Scholar
Soleimannejad, J.; Aghabozorg, H.; Sheashmani, S. 4-(4-Pyridyl)pyridinium bis(pyridine-2,6-dicarboxylato)ferrate(III) tetrahydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2010, 66, m411.10.1107/S1600536810008597Search in Google Scholar PubMed PubMed Central
Soleimannejad, J.; Aghabozorg, H.; Mahammadzadeh, Y.; Nasibipour, M.; Sheshmani, S.; Shokrollahis, A.; Karamani, E.; Shamsipur, M. Different complexation Behavior of Fe(III), Co(II) and Ni(II) with pyridine-2,6-dicarboxylic acid and 4,4′-Bipyridine adduct: syntheses, crystal structures and solution studies. J. Iran Chem. Soc.2011, 8, 247–264.10.1007/BF03246222Search in Google Scholar
Tabatabaee, M.; Abbasi, F.; Kukovec, B.M.; Nasirizadeh, N. Preparation and structural, spectroscopic, thermal, and electrochemical characterizations of iron(III) compounds containing dipicolinate and 2-aminopyrimidine or acridine. J. Coord. Chem.2011, 64, 1718–1728.10.1080/00958972.2011.580843Search in Google Scholar
Tabatabaee, M.; Afraziyan, S.; Nasirizadeh, N. Synthesis and characterization a novel co-crystal of acridinium bis(pyridine-2,6-dicarboxylato) iron(III), acridine, and water molecule, {[(Hacr)[Fe(pydc)2]}2acr H2O. Synth. React. Inorg. Met.-Org., Nano-Met. Chem.2013b, 43, 1181–1185.10.1080/15533174.2012.756901Search in Google Scholar
Tabatabaee, M.; Dadkhodaee, M.; Kukovec, B.M. Different coordination environments of iron(III) and pseudopolymorphism in complexes with dipicolinic acid and 2-amino-6-picoline. The influence of molar ratio and solvent type. Polyhedron2013a, 51, 316–322.10.1016/j.poly.2012.12.033Search in Google Scholar
Uhrecký, R.; Padelková, Z.; Moncoľ, J.; Koman, M.; Dlháň, Ľ.; Titiš, J.; Boča, R. Synthesis, crystal structure, spectra and magnetic properties of new manganese(III) and iron(III) dipicolinate complexes. Polyhedron2013, 56, 9–17.10.1016/j.poly.2013.03.026Search in Google Scholar
Uhrecký, R.; Pavlik, J.; Ružičková Z.; Dlháň, Ľ.; Koman, M.; Boča, R.; Moncoľ, J. Synthesis, crystal structure and magnetism of iron(III) and manganese(III) dipicolinates with pyridinemethanols. J. Mol Struct.2014, 1076, 10–19.10.1016/j.molstruc.2014.07.037Search in Google Scholar
Uhrecký, R.; Svoboda, I.; Ružičková Z.; Koman, M.; Dlháň, Ľ.; Pavlík, J.; Moncoľ, J.; Boča, R. Synthesis, structure and magnetism of manganese and iron dipicolinates with N,N′-donor ligands. Inorg. Chim. Acta2015, 425, 134–144.10.1016/j.ica.2014.10.006Search in Google Scholar
Wolf, M.; Klufers, P. Structure and bonding of high-spin nitrosyl-iron(II) compounds with mixed N,O-chelators and aqua ligands. Eur. J. Inorg. Chem.2017, 2303–2312. DOI:10.1002/ejic.201601329.10.1002/ejic.201601329Search in Google Scholar
Xu, W.; Lin, J.L.; Zhu, H.L.; Hu, F.H.; Zheng, Y.Q. Synthesis, crystal structure and magnetic properties of an iron(III) pyridine-2,3,5,6-tetracarboxylate complex. Z. Naturforsch, B, Chem. Sci2011, 66, 465–470.10.1515/znb-2011-0505Search in Google Scholar
Zhao, L.; Dong, Y.R.; Xie, H.Z. Bis[4-(4-pyridyl)pyridinium] (4-carboxypyridine-2,6-dicarboxylato-κ3O2,N,O6)(pyridine-2,4,6-tricarboxylato-κ3O2,N,O6)ferrate(III) trihydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2009, 65, m450–m451.10.1107/S1600536809010514Search in Google Scholar PubMed PubMed Central
Zhou, G.W.; Wu, A.Q.; Wang, M.S.; Guo, G.C.; Huang, J.S. Diaquachlorido(4-hydroxypyridine-2,6-carboxylato-κ3N,O,O′)iron(III) 18-crown-6 dihydrate. Acta Crystallogr., Sect. E, Struct. Rep. Online2007, 63, m2463–m2464.10.1107/S1600536807041955Search in Google Scholar
Zhou, J.P.; Chen, M.H.; Li, M.J.; Xing, Q.J.; Zhang, A.Q.; Peng, Q. 3-D Hydrogen-bonded networks of metal complexes with chelidamic acid and 1,10-phenanthroline: syntheses, structures, and optical properties. J. Coord. Chem.2010, 63, 3576–3588.10.1080/00958972.2010.513006Search in Google Scholar
©2020 Walter de Gruyter GmbH, Berlin/Boston