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transition metal carbyne complex wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 synthesis toggle synthesis subsection 1 1 bridging alkylidyne ligands in cluster compounds 2 structure 3 reactions and applications 4 main group analogue 5 further reading 6 references toggle the table of contents transition metal carbyne complex 3 languages čeština italiano українська edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia transition metal carbyne complexes are organometallic compounds with a triple bond between carbon and the transition metal 1 this triple bond consists of a σ bond and two π bonds 2 the homo of the carbyne ligand interacts with the lumo of the metal to create the σ bond the two π bonds are formed when the two homo orbitals of the metal back donate to the lumo of the carbyne they are also called metal alkylidynes the organic fragment containing the carbon bonded to the metal is a carbyne ligand such compounds are useful in organic synthesis of alkynes and nitriles they have been the focus of much fundamental research 3 synthesis edit transition metal carbyne complexes are most common for the early transition metals especially niobium tantalum molybdenum tungsten and rhenium they can also have low valence metals as well as high valence metals protonation of a re i vinylidene complex to give the corresponding cationic re v carbyne derivative the first fischer carbyne complex was reported in 1973 4 two years later in 1975 the first schrock carbyne was reported 5 many high valent carbyne complexes have since been prepared often by dehydrohalogenation of carbene complexes alternatively amino substituted carbyne ligands sometimes form upon protonation of electron rich isonitrile complexes similarly o protonation of μ 3 co ligands in clusters gives hydroxycarbyne complexes vinyl ligands have been shown to rearrange into carbyne ligands addition of electrophiles to vinylidene ligands also affords carbyne complexes 3 bridging alkylidyne ligands in cluster compounds edit methylidynetricobaltnonacarbonyl formula hcco 3 co 9 is a metal cluster that contains the methylidyne ligand some metal carbynes dimerize to give dimetallacyclobutadienes in these complexes the carbyne ligand serves as a bridging ligand several cluster bound carbyne complexes are known typically with co ligands these compounds do not feature mc triple bonds instead the carbyne carbon is tetrahedral tricobalt derivatives are prepared by treating cobalt carbonyl with haloforms 6 2 hcbr 3 9 2 co 2 co 8 2 hcco 3 co 9 18 co 3 cobr 2 structure edit structure of phcw obu t 3 7 monomeric metal carbyne complexes exhibit fairly linear m c r linkages according to x ray crystallography the m c distances are typically shorter than the m c bonds found in metal carbenes the bond angle is generally between 170 and 180 8 analogous to fischer and schrock carbenes fischer and schrock carbynes are also known fischer carbynes usually have lower oxidation state metals and the ligands are π accepting electron withdrawing ligands schrock carbynes on the other hand typically have higher oxidation state metals and electron donating anionic ligands in a fischer carbyne the c carbyne exhibits electrophilic behavior while schrock carbynes display nucleophilic reactivity on the carbyne carbon 9 in 2025 radical reactivity at the carbyne carbon was also reported 10 carbyne complexes have also been characterized by many methods including infrared spectroscopy raman spectroscopy and single crystal x ray diffraction 11 bond lengths bond angles and structures can be inferred from these and other analytical techniques metal carbyne complexes also exhibit a large trans effect where the ligand opposite the carbyne is typically labile reactions and applications edit hexa tert butoxy ditungsten iii is a catalyst for alkyne metathesis 12 the catalytic cycle involves a carbyne intermediate 13 some carbyne complexes react with electrophiles at c carbyne followed by association of the anion the net reaction gives a transition metal carbene complex l n m cr hx l n x m chr these complexes can also undergo photochemical reactions in some carbyne complexes coupling of the carbyne ligand to a carbonyl is observed protonation of the carbyne carbon and conversion of the carbyne ligand into a π allyl 14 main group analogue edit a sulfur based main group analog of a carbyne complex has been prepared by seppalt and coworkers 15 the compound trifluoro 2 2 2 trifluoroethylidyne λ 6 sulfurane f 3 c c sf 3 prepared by dehydrofluorination of f 3 c ch sf 4 or f 3 c ch 2 sf 5 is an unstable gas that readily undergoes dimerization to form trans cf 3 sf 3 c c cf 3 sf 3 above 50 c further reading edit mayr a bastos c m 1992 coupling reactions of terminal two faced π ligands and related cleavage reactions progress in inorganic chemistry vol 40 pp 1 98 doi 10 1002 9780470166413 ch1 isbn 9780470166413 cite book journal ignored help references edit cui mingxu jia guochen 2022 07 20 organometallic chemistry of transition metal alkylidyne complexes centered at metathesis reactions journal of the american chemical society 144 28 12546 12566 doi 10 1021 jacs 2c01192 issn 0002 7863 pmid 35793547 kim heesook p angelici robert j 1987 transition metal complexes with terminal carbyne ligands advances in organometallic chemistry vol 27 pp 51 111 doi 10 1016 s0065 3055 08 60026 x isbn 9780120311279 cite book journal ignored help 1 2 elschenbroich c 2006 organometallics weinheim wiley vch isbn 978 3 527 29390 2 fischer e o kreis g kreiter c g muller j huttner g lorenz h 1973 trans halogeno alkyl aryl carbin tetracarbonyl komplexe von chrom molybdän und wolfram ein neuer verbindungstyp mit übergangsmetall kohlenstoff dreifachbindung trans halogenoalkyl aryl carbynetetracarbonyl complexes of chromium molybdenum and tungsten a new type of compound with a transition metal carbon triple bond angew chem 85 14 618 620 bibcode 1973angch 85 618f doi 10 1002 ange 19730851407 guggenberger l j schrock r r 1975 tantalum carbyne complex j am chem soc 97 10 2935 doi 10 1021 ja00843a072 seyferth dietmar nestle mara o hallgren john s 2007 μ 3 alkylidyne tris trigarbonylcobalt compounds organocobalt cluster complexes inorganic syntheses vol 20 pp 224 224 226 doi 10 1002 9780470132517 ch52 isbn 9780470132517 cite book journal ignored help cotton f albert schwotzer willi shamshoum edwar s 1985 further studies of the reactions of ditungsten hexa t butoxide with acetylenes isolation and characterization of wo ocme3 4 thf w 3 ocme 3 5 μ o μ cc 3 h 7 o 2 and w cph ocme 3 3 journal of organometallic chemistry 296 1 2 55 68 doi 10 1016 0022 328x 85 80338 7 spessard gary o miessler gary l 2015 organometallic chemistry 2nd ed oxford university press pp 439 449 isbn 9780199342679 crabtree r h 2014 the organometallic chemistry of the transition metals 6th ed new york ny wiley pp 290 315 isbn 9781118138076 deng zhihong ye shengfa jiang xuelian zhang xinchao chen dafa huang zhe tao lizhi liu jiaojiao ni yong 2025 04 21 radical additions of carbyne to achieve metalla aromatic radicals chemrxiv doi 10 26434 chemrxiv 2025 gw265 retrieved 2025 05 14 kreißl f r 5 december 2012 transition metal carbyne complexes springer isbn 9789401047289 fürstner alois 2021 09 29 the ascent of alkyne metathesis to strategy level status journal of the american chemical society 143 38 15538 15555 doi 10 1021 jacs 1c08040 issn 0002 7863 pmc 8485352 pmid 34519486 listemann mark l schrock richard r 1985 multiple metal carbon bonds 35 a general route to tri tert butoxytungsten alkylidyne complexes scission of acetylenes by ditungsten hexa tert butoxide organometallics 4 74 83 doi 10 1021 om00120a014 kingsbury k b carter j d mcelwee white l 1990 formation of cyclopentenone upon photo oxidation of the cyclopropyl c c 3 h 5 carbyne complex η 5 c 5 h 5 p ome 3 co w c c c 3 h 5 j chem soc chem commun 1990 8 624 625 doi 10 1039 c39900000624 poetter brigitte seppelt konrad simon arndt peters eva maria hettich bernhard february 1985 trifluoroethylidynesulfur trifluoride cf3c tplbond sf3 and its dimer journal of the american chemical society 107 4 980 985 doi 10 1021 ja00290a038 issn 0002 7863 v t e organometallic chemistry principles crystal field theory ligand field theory 18 electron rule d electron count polyhedral skeletal electron pair theory isolobal principle π backbonding dewar chatt duncanson model hapticity spin states agostic interaction metal ligand multiple bond reactions oxidative addition reductive elimination migratory insertion β hydride elimination transmetalation carbometalation hydrometalation types of compounds gilman reagents grignard reagents cyclopentadienyl complexes transition metal indenyl complexes transition metal fullerene complexes metallocenes metal tetranorbornyls sandwich compounds half sandwich compounds transition metal acyl complexes transition metal carbene complexes transition metal carbyne complexes transition metal alkene complexes transition metal alkyne complexes transition metal allyl complexes transition metal carbides arene complexes of univalent gallium indium and thallium applications carbonylation cativa process grignard reaction monsanto process olefin metathesis shell higher olefin process ziegler natta process related branches of chemistry organic chemistry inorganic chemistry bioinorganic chemistry category v t e coordination complexes h donors h h 2 bh 4 b donors br 2 bh 4 b m h n c donors r rc o hc o ch 2 chch 2 allyl c ch 2 3 ch 2 ch 2 h 2 c ch ch ch 2 cr cr 2 rc 2 r c 6 h 4 cn cp co co 2 c 4 c 6 r 6 c 60 c 70 rnc cr 2 cr c 5 h 5 c 9 h 7 cs r 2 cs rc s h c cr 2 cs 2 si donors h n sir 4 n r 3 si n donors nh 3 h 2 nch 2 ch 2 nh 2 etc n 3 nco imidazole no rno no 2 py amino acid n 3 rn 2 rcn bipy phen porphyrin me 3 si 2 n n 2 ncs p donors pr 3 pf 3 pr 2 pr 2 oh as donors asr 3 bi donors r n bi n rbi o donors h 2 o oh r 2 o ro o 2 o 2 o 2 2 4 co 2 3 hco 3 c 2 o 2 4 rco 2 rconr 2 oc nr 2 2 acac r 2 co ono no 3 clo 4 c 5 h 5 no osr 2 so 2 4 po 3 4 opr 3 s donors rs hs and h 2 s r 2 s so so 2 so 2 3 s 2 o 2 3 sr 2 o ncs cs 2 r 2 ncs 2 r 2 c 2 s 2 2 r 2 cs rc s h ch csr 2 halide donors f f 2 cl br i retrieved from https en wikipedia org w index php title transition_metal_carbyne_complex oldid 1356365010 categories organometallic chemistry coordination complexes transition metal compounds hidden category cs1 errors periodical ignored this page was last edited on 27 may 2026 at 09 01 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents transition metal carbyne complex 3 languages add topic