Rodosena: Perbedaan antara revisi

Karena stabilitas dan kemudahan persiapan relatifnya, garam rodosenium adalah bahan awal yang biasa untuk menyiapkan rodosena dan rodosena tersubstitusi, yang semuanya tidak stabil. Sintesis awal menggunakan anion siklopentadienil dan [[Logam asetilasetonat|tris(asetilasetonato)rodium(III)]];<ref name="JACS_1953" /> banyak pendekatan lain telah dilaporkan, termasuk [[transmetalasi]] redoks fase gas<ref name="JACS_1982"/> dan menggunakan prekursor [[Senyawa setengah sandwich|setengah-sandwich]].<ref name="He_PhD"/> Oktafenilrodosena (suatu turunan dengan delapan [[gugus fenil]] yang menempel) adalah rodosena tersubstitusi pertama yang diisolasi pada suhu kamar, meskipun ia terurai cepat di udara. [[Kristalografi sinar-X]] menegaskan bahwa oktafenilrodosena memiliki struktur sandwich dengan [[konformasi silangbersilang]].<ref name="Collins_1995"/> Tidak seperti kobaltosena, yang telah menjadi [[Reduktor|agen pereduksi]] satu elektron yang bermanfaat dalam penelitian,<ref name="cobaltocenium"/> tidak ada turunan rodosena yang ditemukan cukup stabil untuk aplikasi semacam itu.

Penemuan dalam [[kimia organologam]] telah mengarah pada wawasan penting ke dalam [[ikatan kimia]]. [[Garam Zeise]], K[PtCl₃(C₂H₄)]·H₂O, dilaporkan tahun 1831<ref name="Zeise discovery" /> dan penemuan [[Ludwig Mond|Mond]] pada Ni(CO)₄ terjadi tahun 1888.<ref name="leigh-2002"/> Masing-masing mengandung ikatan antara pusat logam dan molekul kecil, [[etilena]] dalam kasus garam Zeise dan [[karbon monoksida]] dalam kasus [[nikel tetrakarbonil]].<ref name="Zeise review" /> Model ruang terisi dari anion garam Zeise (gambar kiri)<ref name="Zeise anion 1"/><ref name="Zeise anion 2"/> menunjukkan ikatan langsung antara pusat logam [[platina]] (ditunjukkan dengan warna biru) dan atom karbon (ditampilkan dalam warna hitam) dari [[ligan]] etilena; ikatan logam–karbon tersebut adalah karakteristik yang menentukan dari spesi [[organologam]]. Model ikatan tidak dapat menjelaskan sifat ikatan logam–alkena sampai [[model Dewar-Chatt-Duncanson]] diusulkan pada tahun 1950-an.<ref name="Dewar-Chatt-DuncansonDCW 1"/><ref name="DCW 1Dewar-Chatt-Duncanson"/><ref name="DCW 2"/><ref name="astruc-2007"/> Formulasi awal hanya melingkupi ikatan logam–alkena<ref name="leigh-2002"/> tetapi model tersebut diperluas dari waktu ke waktu untuk mencakup sistem seperti [[logam karbonil]] (termasuk [Ni(CO)₄]) di mana [[ikatan balik π]] sangat penting.<ref name=astruc-2007/>

Sifat-sifat kobaltosenkobaltosena yang dilaporkan oleh Wilkinson dan Fischer menunjukkan bahwa kation kobaltisinium unipositif [Co(C₅H₅)₂]⁺ menunjukkan stabilitas yang mirip dengan ferrocene itu sendiri. Pengamatan ini tidak terduga mengingat bahwa kation kobaltisinium dan ferosena adalah [[isoelektronik]], meskipun ikatan tidak dipahami pada saat itu. Namun demikian, pengamatan tersebut mengarahkan Wilkinson dan [[F. Albert Cotton]] untuk mencoba sintesis [[garam]] rodosenium<ref name=cenium-cinium group=Note/> dan iridosenium.<ref name="JACS_1953" /> Mereka melaporkan sintesis banyak garam rodosenium, termasuk yang mengandung anion [[bromida|tribromida]] ([Rh(C₅H₅)₂]Br₃), [[perklorat]] ([Rh(C₅H₅)₂]ClO₄), dan [[garam Reinecke|reineckat]] ([Rh(C₅H₅)₂] [Cr(NCS)₄(NH₃)₂]·H₂O), serta menemukan bahwa penambahan dipikrilamina menghasilkan senyawa yang mengandung [Rh(C₅H₅)₂] [N(C₆H₂N₃O₆)₂].<ref name="JACS_1953" /> Dalam setiap kasus, kation rodosenium ditemukan memiliki stabilitas yang tinggi. Wilkinson dan Fischer melanjutkan untuk berbagi [[Hadiah Nobel dalam Kimia]] tahun 1973 "untuk karya rintisan mereka, yang dilakukan secara independen, pada kimia organologam, yang disebut [[senyawa sandwich]]".<ref name="Nobel Prize"/><ref name="New Scientist Nobel Prize"/>

Stabilitas metalosena dapat langsung dibandingkan dengan melihat [[potensial reduksi]] pada [[reduksi]] satu elektron dari kation unipositif. Data berikut disajikan relatif terhadap [[elektrodaelektrode kalomel jenuh]] (SCE) dalam [[asetonitril]]:

Data ini jelas menunjukkan stabilitas ferosena netral dan kation kobaltosenium dan rodosenium. Rodosena adalah sekitar 500&nbsp;mV lebih mereduksi daripada kobaltosena, menunjukkan bahwa lebih mudah teroksidasi dan karenanya kurang stabil.<ref name="El_Murr_1979" /> Investigasi [[polarografi]] awal dari rodosenium perklorat pada [[pH]] netral menunjukkan puncak gelombang katodik pada −1.53&nbsp;V (versus SCE) pada [[elektrodaelektrode raksa tetes]], sesuai dengan formasi rodosena dalam larutan, tetapi para peneliti tidak dapat mengisolasi produk netral dari larutan. Dalam penelitian yang sama, upaya untuk mendeteksi [[iridosena]] dengan memaparkan garam iridosenium ke dalam kondisi oksidasi tidak berhasil bahkan pada pH tinggi.<ref name="JACS_1953" /> Data ini konsisten dengan rodosena yang sangat tidak stabil dan dapat menunjukkan bahwa iridosena bahkan lebih tidak stabil lagi.

Telah ada penelitian ekstensif ke dalam [[metalofarmaseutika]],<ref name=clarke-1999/><ref name=jones-2007/> termasuk diskusi tentang senyawa rodium dalam kedokteran.<ref name="Rh in medicine"/> Sebuah badan penelitian yang substansial telah meneliti menggunakan turunan metalosena dari [[rutenium]]<ref name=clarke-2002/> dan besi<ref name=fouda-2007/> sebagai metalofarmaseutika. Salah satu bidang penelitian tersebut telah menggunakan metalosena dalam gugus fluorofenil di [[haloperidol]],<ref name="Wenzel"/> yang merupakan [[obat-obatan]] yang digolongkan sebagai [[antipsikotik tipikal]]. Senyawa ferosenil–haloperidol diteliti memiliki struktur (C₅H₅)Fe(C₅H₄)–C(=O)–(CH₂)₃–N(CH₂CH₂)₂C(OH)–C₆H₄Cl dan dapat diubah menjadi analog ruteniumnya melalui reaksi transmetalasi. Menggunakan [[isotop]] [[radioaktif]] [[rutenium-103|¹⁰³Ru]] menghasilkan suatu radiofarmaka rutenosenil–haloperidol dengan afinitas tinggi bagi [[paru-paru]] namun tidak pada [[jaringan (biologi)|jaringan]] [[otak]] pada [[tikus]].<ref name="Wenzel" /> [[Peluruhan beta]] dari ¹⁰³Ru menghasilkan [[Isomer nuklir#Isomer metastabil|isotop metastabil]] [[rodium-103m|^103''m''Rh]] dalam suatu senyawa rodosenil–haloperidol. Senyawa ini, seperti turunan rodosena lainnya, memiliki konfigurasi elektron valensi-19 yang tidak stabil dan cepat teroksidasi menjadi spesi kation rodosenium–haloperidol yang diharapkan.<ref name="Wenzel" /> Pemisahan spesi rutenosenil–haloperidol dan rodosenium–haloperidol serta distribusinya dalam masing-masing organ tubuh telah dipelajari.<ref name="organ distrib"/> ^103''m''Rh memiliki [[waktu paruh]] 56&nbsp;menit dan memancarkan [[sinar gama]] dengan energi 39.8&nbsp;[[Elektronvolt|keV]], sehingga [[peluruhan gama]] isotop rodium harus diikuti segera setelah peluruhan beta isotop rutenium. [[Radionuklida]] pemancar beta- dan gamma yang digunakan secara medis termasuk [[iodin-131|¹³¹I]], [[Radiofarmakologi#Besi-59|⁵⁹Fe]], dan [[Radiofarmakologi#Kalsium-47|⁴⁷Ca]], serta ^103''m''Rh telah diusulkan untuk penggunaannya dalam [[radioterapi]] bagi tumor kecil.<ref name="Rh in medicine" />

<ref name="astruc-2007">{{cite book |last= Astruc |first=D. |authorlink= Didier Astruc |year= 2007 |title= Organometallic Chemistry and Catalysis |location= Berlin |publisher= [[Springer Science+Business Media|Springer]] |pages= 41–43 |isbn= 978-3-540-46128-9 |url= https://books.google.com/books?id=aVyfo52-nRsC&pg=PA41 |language=en}}</ref>

<ref name="baghurst-1989">{{Cite journal |last1= Baghurst |first1= D. R. |last2= Mingos |first2= D. M. P. |authorlink2= Michael Mingos |last3= Watson |first3= M. J. |year= 1989 |title= Application of Microwave Dielectric Loss Heating Effects for the Rapid and Convenient Synthesis of Organometallic Compounds |journal= [[Journal of Organometallic Chemistry]] |volume= 368 |issue= 3 |pages= C43–C45 |doi= 10.1016/0022-328X(89)85418-X |language=en}}</ref>

<ref name="baghurst-1990">{{Cite journal |last1= Baghurst |first1= D. R. |last2= Mingos |first2= D. M. P. |authorlink2= Michael Mingos |year= 1990 |title= Design and Application of a Reflux Modification for the Synthesis of Organometallic Compounds Using Microwave Dielectric Loss Heating Effects |journal= [[Journal of Organometallic Chemistry]] |volume= 384 |issue= 3 |pages= C57–C60 |doi= 10.1016/0022-328X(90)87135-Z |language=en}}</ref>

<ref name="Chromatographia">{{cite journal |last1= Andre |first1=M. |last2= Schottenberger |first2=H. |last3= Tessadri |first3=R. |last4= Ingram |first4=G. |last5= Jaitner |first5=P. |last6= Schwarzhans |first6=K. E. |year=1990 |title= Synthesis and Preparative HPLC-Separation of Heteronuclear Oligometallocenes. Isolation of Cations of Rhodocenylferrocene, 1,1'-Dirhodocenylferrocene, and 1-Cobaltocenyl-1'-rhodocenylferrocene |journal= [[Chromatographia]] |volume= 30 |issue= 9–10 |pages= 543–545 |doi= 10.1007/BF02269802 |language=en}}</ref>

<ref name="clarke-1999">{{cite book |author1= Clarke, M. J. |author2= Sadler, P. J. |year= 1999 |title= Metallopharmaceuticals: Diagnosis and therapy |location= Berlin |publisher= Springer |isbn= 3-540-65308-2 |language=en}}</ref>

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<ref name="Collins_1995">{{Cite journal |last1= Collins |first1= J. E. |last2= Castellani |first2= M. P. |last3= Rheingold |first3= A. L. |last4= Miller |first4= E. J. |last5= Geiger |first5= W. E. |last6= Rieger |first6= A. L. |last7= Rieger |first7= P. H. |year= 1995 |title= Synthesis, Characterization, and Molecular-Structure of Bis(tetraphenylcyclopentadienyl)rhodium(II) |journal= [[Organometallics]] |volume= 14 |issue= 3 |pages= 1232–1238 |doi= 10.1021/om00003a025 |language=en}}</ref>

<ref name="Crabtree">{{cite book |last= Crabtree |first= R. H. |authorlink= Robert H. Crabtree |year= 2009 |title= The Organometallic Chemistry of the Transition Metals |edition= 5th5 |location= Hoboken, NJ |publisher= John Wiley and Sons |isbn= 978-0-470-25762-3 |page= 2 |url= https://books.google.com/books?id=WLb962AKlSEC&pg=PA2 |quote= An industrial application of transition metal organometallic chemistry appeared as early as the 1880s, when Ludwig Mond showed that nickel can be purified by using CO to pick up nickel in the form of gaseous Ni(CO)₄ that can easily be separated from solid impurities and later be thermally decomposed to give pure nickel.<p>... Recent work has shown the existence of a growing class of metalloenzymes having organometallic ligand environments – considered as the chemistry of metal ions having C-donor ligands such as CO or the methyl group |language=en}}</ref>

<ref name="DCW 1">{{cite book |title= Modern Coordination Chemistry: The Legacy of Joseph Chatt |editor1-last= Leigh |editor1-first= G. J. |editor2-last= Winterton |editor2-first= N. |year= 2002 |publisher= [[RSC Publishing]] |chapter= Some Notes on the Early Development of Models of Bonding in Olefin-Metal Complexes |last= Winterton |first= N. |pages= 103&ndash;110103–110 |isbn= 9780854044696 |url= https://books.google.com/books?id=VoBxtPb5zCcC&pg=PA103 |language=en}}</ref>

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<ref name="ferrocenium redox couple">{{cite journal |last1= Pavlishchuk |first1=V. V. |last2= Addison |first2=A. W. |year= 2000 |title= Conversion Constants for Redox Potentials Measured Versus Different Reference Electrodes in Acetonitrile Solutions at 25&nbsp;°C |journal= [[Inorganica Chimica Acta]] |volume= 298 |issue= 1 |pages= 97–102 |doi= 10.1016/S0020-1693(99)00407-7 |language=en}}</ref>

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<ref name="He_PhD">{{Cite book |last= He |first= H. T. |title= Synthesis and Characterisation of Metallocenes Containing Bulky Cyclopentadienyl Ligands |type= PhD thesis |year= 1999 |location= [[University of Sydney]] |oclc=222646266 |language=en}}</ref>

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<ref name="jones-2007">{{cite book |last1= Jones |first1=C. J. |last2= Thornback |first2=J. |year= 2007 |title= Medicinal Applications of Coordination Chemistry |location= Cambridge, UK |publisher= RSC Publishing |isbn= 978-0-85404-596-9 |language=en}}</ref>

<ref name="Keller_1967">{{Cite journal |last1= Keller |first1= H. J. |last2= Wawersik |first2= H. |year= 1967 |title= Spektroskopische Untersuchungen an Komplexverbindungen. VI. EPR-spektren von (C₅H₅)₂Rh und (C₅H₅)₂Ir |trans-title= Spectroscopic studies of complex compounds. VI. EPR spectra of (C₅H₅)₂Rh and (C₅H₅)₂Ir |journal= [[Journal of Organometallic Chemistry]] |volume= 8 |issue= 1 |pages= 185–188 |language= Germande |doi= 10.1016/S0022-328X(00)84718-X}}</ref>

<ref name="leigh-2002">{{cite book |editor1-last= Leigh |editor1-first= G. J. |editor2-last= Winterton |editor2-first= N. |year= 2002 |chapter= Section D: Transition Metal Complexes of Olefins, Acetylenes, Arenes and Related Isolobal COmpounds |title= Modern Coordination Chemistry: The Legacy of Joseph Chatt |location= Cambridge, UK |publisher= RSC Publishing |pages= 101–110 |isbn= 0-85404-469-8 |url= https://books.google.com/books?id=VoBxtPb5zCcC&pg=PA101 |language=en}}</ref>

<ref name="linked metallocenes">{{cite journal |last1= Barlow |first1=S. |last2= O'Hare |first2=D. |year= 1997 |title= Metal–Metal Interactions in Linked Metallocenes |journal= [[Chemical Reviews]] |volume= 97 |issue= 3 |pages= 637–670 |doi= 10.1021/cr960083v |language=en}}</ref>

<ref name="Nobel Prize">{{cite web |url= http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/ |title= The Nobel Prize in Chemistry 1973 |publisher= [[Nobel Foundation]] |accessdate= 12 September 2010 |language=en}}</ref>

<ref name="New Scientist Nobel Prize">{{cite journal |url= https://books.google.com.au/books?id=UJd_rRSXJPcC&pg=PA335 |title= Metal Sandwiches |journal= [[New Scientist]] |date= 1 November 1973 |accessdate= 17 June 2017 |volume= 60 |issue= 870 |page= 335 |last= Sherwood |first= Martin |authorlink= Martin Sherwood |language=en}}</ref>

<ref name="organ distrib">{{Cite journal |last1= Wenzel |first1= M. |last2= Wu |first2= Y. F. |year= 1987 |title= Abtrennung von [^103''m''Rh]Rhodocen-Derivaten von den Analogen [¹⁰³Ru]Ruthenocen-Derivaten und deren Organ-Verteilung |trans-title = Separation of [^103''m''Rh]rhodocene derivatives from the parent [¹⁰³Ru]ruthenocene derivatives and their organ distribution |language= Germande |journal= [[International Journal of Radiation Applications and Instrumentation A]] |volume= 38 |issue= 1 |pages= 67–69 |pmid= 3030970 |doi= 10.1016/0883-2889(87)90240-1}}</ref>

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<ref name="Wagner_2006">{{cite journal |last= Wagner |first=M. |year= 2006 |title= A New Dimension in Multinuclear Metallocene Complexes |journal= [[Angewandte Chemie International Edition]] |volume= 45 |issue= 36 |pages= 5916–5918 |doi= 10.1002/anie.200601787 |language=en}}</ref>

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<ref name="Yan-2015">{{cite journal |last1= Yan|first1 = Y.|last2= Deaton|first2= T. M.|last3= Zhang|first3= J.|last4= Hongkun|first4= H.|last5= Hayat|first5= J.|last6= Pageni|first6= P.|last7= Matyjaszewski|first7= K.|last8= Tang|first8= C.|title= The Syntheses of Monosubstituted Rhodocenium Derivatives, Monomers and Polymers|journal= [[Macromolecules (journaljurnal)|Macromolecules]] |year= 2015|volume= 48|issue= 6|pages= 1644–1650|doi= 10.1021/acs.macromol.5b00471|bibcode= 2015MaMol..48.1644Y |language=en}}</ref>

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<ref name="Zeise review">{{cite journal |last= Hunt |first= L. B. |year= 1984 |title= The First Organometallic Compounds: William Christopher Zeise and his Platinum Complexes |journal= [[Platinum Metals Review]] |volume= 28 |issue= 2 |pages= 76–83 |url= http://www.platinummetalsreview.com/pdf/pmr-v28-i2-076-083.pdf |language= en |access-date= 2018-07-12 |archive-date= 2015-09-24 |archive-url= https://web.archive.org/web/20150924074325/http://www.platinummetalsreview.com/pdf/pmr-v28-i2-076-083.pdf |dead-url= yes }}</ref>}}