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Cyclopentadienyl iron dicarbonyl styrene chalcogenosulfonates: synthesis and structure of CpFe(CO)2SeSO2CH=CHPh

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Abstract

In this contribution, we report the preparation of iron thiosulfonato complex CpFe(CO)2SSO2CH=CHPh (1) and its selenosulfonato analogue CpFe(CO)2SeSO2CH=CHPh (2) featuring styrene moiety. 1 and 2 are obtained by electrophilic attack of (μ-Ex)[CpFe(CO)2]2 (E = S; x = 2–4, E = Se; x = 1) on the sulfur atom of styrene sulfonyl chloride ClSO2CH=CHPh. The new compounds, 1 and 2 have been characterized by elemental analyses, IR, 1H-, 13C{1H}-NMR, UV–Vis spectroscopy and the structure of 2 is determined by X-ray crystallography.

Graphical abstract

In this contribution, we report the preparation of iron thiosulfonato complex CpFe(CO)2SSO2CH=CHPh (1) and its selenosulfonato analogue CpFe(CO)2SeSO2CH=CHPh (2) featuring styrene moiety. 1 and 2 are obtained by electrophilic attack of (μ-Ex)[CpFe(CO)2]2 (E = S; x = 2–4, E = Se; x = 1) on the sulfur atom of styrene sulfonyl chloride ClSO2CH=CHPh. The new compounds, 1 and 2 have been characterized by elemental analyses, IR, 1H-, 13C{1H}-NMR, UV–Vis spectroscopy and the structure of 2 is determined by X-ray crystallography..

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References

  1. Braymer J J, Freibert S A, Rakwalska-Bange M and Lill R 2021 Mechanistic concepts of iron-sulfur protein biogenesis in biology Biochim. Biophys. Acta, Mol. Cell Res. 1886 118863

  2. Jeong H S, Hong S, Yoo H S, Kim J, Kim Y, Yoon C, Lee S J and Kim S H 2021 EPR-derived structures of flavin radical and iron-sulfur clusters from Methylosinus sporium 5 reductase Inorg. Chem. Front. 1279

  3. Nie X, Jäger A, Börner J and Klug G 2021 Interplay between formation of photosynthetic complexes and expression of genes for iron–sulfur cluster assembly in Rhodobacter sphaeroides? Photosyn. Res. 147 39

    Article  CAS  Google Scholar 

  4. Deane C 2020 An iron-sulfur grip Nature Chem. Bio. 16 481

    Article  CAS  Google Scholar 

  5. Buratto W R, Ferreira R B, Catalano V J, García-Serres R and Murray L J 2021 Cleavage of cluster iron–sulfide bonds in cyclophane-coordinated FenSm complexes Dalton Trans. 50 816

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Kertess L, Wittkamp F, Sommer C, Esselborn J, Rüdiger O, Reijerse E J, et al 2017 Chalcogenide substitution in the [2Fe] cluster of [FeFe]-hydrogenases conserves high enzymatic activity Dalton Trans. 46 16947

    Article  CAS  PubMed  Google Scholar 

  7. Weigand W 2019 [FeFe]-hydrogenase mimics: Bio-inspired hydrogen production Phosph. Sil. Sul. Rel. Elem. 194 634

    Article  CAS  Google Scholar 

  8. Harb M K, Alshurafa H, El-khateeb M, Al-Zuheiri A, Görls H, Abul-Futouh H and Weigand W 2018 [FeFe]-hydrogenase models containing long diselenolato linkers ChemSelect 3 8867

    CAS  Google Scholar 

  9. Abul-Futouh H, El-khateeb M, Görls H, Asali K J and Weigand W 2017 Selenium makes the difference: protonation of [FeFe]-hydrogenase mimics with diselenolato ligands Dalton Trans. 46 2937

    Article  CAS  PubMed  Google Scholar 

  10. Wang H, Qiu X, Wang W, Jiang L and Liu H 2019 Iron sulfide nanoparticles embedded into a nitrogen and sulfur co-doped carbon sphere as a highly active oxygen reduction electrocatalyst Front. Chem. 7 855

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Wu X, Markir A, Xu Y, Hu E C, Dai K T, Zhang C, et al. 2019 Rechargeable iron–sulfur battery without polysulfide shuttling Adv. Energy Mat. 9 1902422

    Article  CAS  Google Scholar 

  12. Heift D 2019 Iron sulfide materials: catalysts for electrochemical hydrogen evolution Inorganics 7 75

    Article  CAS  Google Scholar 

  13. Vaccaro B J, Clarkson S M, Holden J F, Lee D-W, Wu C-H, Poole F L II, et al 2017 Biological iron-sulfur storage in a thioferrate-protein nanoparticle Nature Comm. 8 16110

    Article  CAS  Google Scholar 

  14. Maslat A, Jibril I, Abusaud M, Abed-Alhadi A and Hamadeh Z 2002 Synthesis and biological study of a new series of bifunctional organoiron thio- and selenoterephthalate derivatives (C5H5)Fe(CO)2ECO(C6H4)COX (E = S, X = R2N, RNH, NH2, OH, Cl; E = Se, X = RNH, RS, RCOO, NH2, OH, Cl) Appl. Organomet. Chem. 16 44

    Article  CAS  Google Scholar 

  15. Maslat A, Jibril I and Mizyed S 2010 Antimutagenic activities of two suspected anticarcinogenic bifunctional organoiron seleno-terephthalate derivatives Drug Chem. Toxicol. 33 254

    Article  CAS  PubMed  Google Scholar 

  16. El-khateeb M, Al-Noaimi M, Al-Rejjal N, Abul-Futouh H, Görls H and Weigand W 2013 Mono- and bi-iron chalcogencarboxylate complexes Trans. Met. Chem. 38 52917

    Article  Google Scholar 

  17. Al-Jazzazi T, El-khateeb M, Quraan L, Abul-Futouh H, Görls H and Weigand W 2020 Half-sandwich iron complexes bearing vinyl-selenocarboxylato ligands J. Chem. Sci. 132 23

    Article  CAS  Google Scholar 

  18. El-khateeb M, Shaver A and Lebuis A M 2001 The synthesis and structure of the thiosulfonato iron complexes CpFe(CO)2SS(O)2R J. Organomet. Chem. 622 293

    Article  CAS  Google Scholar 

  19. El-khateeb M and Obidate T 2001 The first selenosulfonate complexes CpFe(CO)2SeSO2R: preparation and structure of CpFe(CO)2SeSO2C6H5 Polyhedron 20 2393

    Article  CAS  Google Scholar 

  20. El-khateeb M, Görls H and Weigand W 2007 O-Alkylthio- and O-alkylselenooxalate iron complexes: Structures of CpFe(CO)2ECOCO2Me and [CpFe(CO)2ECO]2 Inorg. Chim. Acta 360 705

    Article  CAS  Google Scholar 

  21. El-khateeb M, Asali K J and Lataifeh A 2003 Half sandwich iron S-bonded mono-thiocarbonate complexes: structure of CpFe(CO)2SCO2Et Polyhedron 22 3105

    Article  CAS  Google Scholar 

  22. El-khateeb M 2004 Iron Se-bonded mono-selenocarbonates CpFe(CO)2SeCO2R: the first selenocarbonate complexes Inorg. Chim. Acta 357 4341

    Article  CAS  Google Scholar 

  23. El-khateeb M, Asali K J and Lataifeh A 2006 Iron dithiocarbonate complexes: Structure of CpFe(CO)2SC(S)O-4-C6H4Cl Polyhedron 25 1695

    Article  CAS  Google Scholar 

  24. El-khateeb M 2006 Selenothiocarbonate complexes of iron: Structure of CpFe(CO)2SeC(S)O-4-C6H4Cl Polyhedron 25 1386

    Article  CAS  Google Scholar 

  25. El-khateeb M, Abul-Futouh H, Görls H, Weigand W and Almazahreh L R 2016 Synthesis, characterization and electrochemical investigations of heterocyclic-selenocarboxylate iron complexes Inorg. Chim. Acta 44 14

    Article  Google Scholar 

  26. El-khateeb M, Abul-Futouh H, Görls H and Weigand W 2019 Towards the synthesis of piano-stool iron complexes mediated by S-alkyl selenothiocarbonato ligands and their substitution reactions Monatsh Chem. 150 1461

    Article  CAS  Google Scholar 

  27. El-khateeb M and Roller A 2007 Synthesis and structures of CpFe(CO)2(κE-ECS2Ph) and [CpFe(CO)(κ2S, E-ECS2Ph)] (E = S, Se) Polyhedron 26 3920

    Article  CAS  Google Scholar 

  28. Jibril I, El-Hinnawi M A and El-khateeb M 1991 Synthesis of a new series of iron complexes Fe(C5H5)(CO)(EPh3)SCOR, Fe(But-C5H4)(CO)(EPh3)SCOR and Fe(1,3-But-C5H3)(CO)(PPh3)SCOR (E = P, As, Sb) through photolytic CO-substitution. Study of the effect of R, E and Cp-substituents on the CO-substitution reactions Polyhedron 10 2095

    Article  CAS  Google Scholar 

  29. El-khateeb M, Lataifeh A and Jibril I 2003 Substituted iron selenocarboxylate complexes CpFe(CO)(EPh3)SeCOR (E = P, As, Sb) Trans. Met. Chem. 28 85

    Article  CAS  Google Scholar 

  30. El-khateeb M, Kumar R and Yousuf S 2020 Halfsandwich iron S-alkyl dithiocarbonato complexes: Synthesis, characterization and reactivity J. Mol. Struct. 1211 28092

    Google Scholar 

  31. El-khateeb M, Harb M K, Mansour A and Yousuf S 2019 Photochemical substitution of a single CO ligand of CpFe(CO)2SeC(Y)Y′Ar [(Y) Y′=(O) O,(S) O and (S) S] by EPh3 (E= P, As, Sb) Inorg. Chim. Acta 286 694

    Article  Google Scholar 

  32. Jibril I, El-khateeb M, Barakat H, Rheinwald G and Lang H 2002 Photolytic CO-substitution reaction of organoiron thiocarboxylate derivatives CpFe(CO)2SCOR (R=alkyl, aryl) with diphosphines (Ph2P(CH2)nPPh2) (n= 1–6): X-ray crystal structure of [CpFe(dppm)SCO(3,5-(NO2)2C6H3)] Inorg. Chim. Acta 333 1

    Article  CAS  Google Scholar 

  33. El-khateeb M, Jibril I, Barakat H, Rheinwald G and Lang H 2003 Controlled synthesis of mono-substituted diphosphine iron thiocarboxylate complexes CpFe(CO)(Ph2P(CH2)nPPh2)SCOR [n= 1 (dppm), n= 2 (dppe)]. X-ray crystal structure of CpFe(CO)(dppm-S)SCO-3,5-(NO2)2C6H3 Polyhedron 22 3445

    Article  CAS  Google Scholar 

  34. El-khateeb M, Asali K J, Al-Noaimi M, Al-Rabaee E, Awwadi F, Taher D and Lang H 2014 Thio-and selenosulfonato complexes of iron bearing aromatic and heterocyclic groups Inorg. Chim. Acta 421 553

    Article  CAS  Google Scholar 

  35. El-khateeb M, Wolfsberger B and Schenk W A 2000 Sulfur (IV) compounds as ligands: Part XXV. Halfsandwich ruthenium thiosulfonato complexes. Crystal and molecular structure of [CpRu(dppe){SSO2(4–C6H4Cl)}] J. Organomet. Chem. 612 14

    CAS  Google Scholar 

  36. El-khateeb M, Görls H and Weigand W 2006 Half-sandwich ruthenium thiocarbonate complexes: Structures of CpRu(PPh3)2SCO2Bun, CpRu(dppe)SCO2Bun and CpRu(PPh3)(CO)SCO2Bun J. Organomet. Chem. 691 5816

    Article  Google Scholar 

  37. El-khateeb M, Asali K J, Abu Salem T and Welter R 2006 Synthesis and characterization of cyclopentadienyltricarbonyl tungsten selenocarboxylate and selenosulfonate complexes Inorg. Chim. Acta 359 4259

    Article  CAS  Google Scholar 

  38. El-Hinnawi M A, Aruffo A A, Santersiero S, McAlister D and Schomaker V 1982 Organometallic sulfur complexes. 1. Syntheses, structures, and characterizations of organoiron sulfane complexes (µ-Sx)[(η5C5H5)[Fe(CO)2]2 (x = 1–4) Inorg. Chem. 22 1585

    Article  Google Scholar 

  39. Herman W A, Rohrmann J and Hecht H 1985 Mehrfachbindungen zwischen hauptgruppenelementen und übergangsmetallen: XVII. Selen- und tellur-brücken in organometallkomplexen: AUFBAU, protonierung und methylierung J. Organomet. Chem. 290 53

    Article  Google Scholar 

  40. SAINT+, version 6.01: Area-Detector Integration Software, Bruker AXS, Madison 2001

  41. Krause L, Herbst-Irmer R, Sheldrick G M and Stalke D 2015 SADABS 2016/02 J. Appl. Crystallogr. 48 3

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. (a) Sheldrick G M 1990 Phase annealing in SHELX-90: direct methods for larger structures Acta Crystallogr. A 46 467; (b) Sheldrick G M 2008 A short history of SHELX Acta Crystallogr. A 64 112

  43. Sheldrick G M 2015 Crystal structure refinement with SHELXL Acta Crystallogr. C 71 3

    Article  Google Scholar 

  44. Farrugia L J 2012 WinGX and ORTEP for windows: an update J. Appl. Crystallogr. 45 849

    Article  CAS  Google Scholar 

  45. El-khateeb M, Asali K J, Al-Junidi B, Abul-Futouh H, Görls H and Weigand W 2020 Synthesis, characterization and electrochemical investigations of heterocyclic-selenocarboxylate iron complexes J. Chem. Sci. 132 22

    Article  CAS  Google Scholar 

  46. Chand A, Sahoo D K, Rana Jena A S and Biswal H S 2020 The prodigious hydrogen bonds with sulfur and selenium in molecular assemblies, structural biology, and functional materials Acc. Chem. Res. 53 1580

    Article  CAS  PubMed  Google Scholar 

  47. Senevirate D S, Uddin M J, Swarambunathan V, Schlegel H B and Endicott J F 2002 Characteristics and properties of metal-to-ligand charge-transfer excited states in 2,3-bis(2-pyridyl)pyrazine and 2,2′-bypyridine ruthenium complexes. Perturbation-theory-based correlations of optical absorption and emission parameters with electrochemistry and thermal kinetics and belated Ab Initio calculations Inorg. Chem. 41 1502

    Article  Google Scholar 

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Acknowledgements

We thank the Deanship of Research, Jordan University of Science and Technology for financial support (Grant No. 243/2020).

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Correspondence to Mohammad El-Khateeb.

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El-Khateeb, M., Al-Momani, A., Garcia-Orduna, P. et al. Cyclopentadienyl iron dicarbonyl styrene chalcogenosulfonates: synthesis and structure of CpFe(CO)2SeSO2CH=CHPh. J Chem Sci 134, 13 (2022). https://doi.org/10.1007/s12039-021-02012-2

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