{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T00:42:17Z","timestamp":1768869737541,"version":"3.49.0"},"reference-count":138,"publisher":"Wiley","issue":"41","license":[{"start":{"date-parts":[[2009,9,11]],"date-time":"2009-09-11T00:00:00Z","timestamp":1252627200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2009,10,19]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The five\u2010coordinate ruthenium N\u2010heterocyclic carbene (NHC) hydrido complexes [Ru(I<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>Me<jats:sub>2<\/jats:sub>)<jats:sub>4<\/jats:sub>H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] (<jats:bold>1<\/jats:bold>; I<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>Me<jats:sub>2<\/jats:sub>=1,3\u2010diisopropyl\u20104,5\u2010dimethylimidazol\u20102\u2010ylidene; Ar<jats:sup>F<\/jats:sup>=3,5\u2010(CF<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>), [Ru(IEt<jats:sub>2<\/jats:sub>Me<jats:sub>2<\/jats:sub>)<jats:sub>4<\/jats:sub>H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] (<jats:bold>2<\/jats:bold>; IEt<jats:sub>2<\/jats:sub>Me<jats:sub>2<\/jats:sub>=1,3\u2010diethyl\u20104,5\u2010dimethylimidazol\u20102\u2010ylidene) and [Ru(IMe<jats:sub>4<\/jats:sub>)<jats:sub>4<\/jats:sub>H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] (<jats:bold>3<\/jats:bold>; IMe<jats:sub>4<\/jats:sub>=1,3,4,5\u2010tetramethylimidazol\u20102\u2010ylidene) have been synthesised following reaction of [Ru(PPh<jats:sub>3<\/jats:sub>)<jats:sub>3<\/jats:sub>HCl] with 4\u20138 equivalents of the free carbenes at ambient temperature. Complexes <jats:bold>1<\/jats:bold>\u2013<jats:bold>3<\/jats:bold> have been structurally characterised and show square pyramidal geometries with apical hydride ligands. In both dichloromethane or pyridine solution, <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> display very low frequency hydride signals at about <jats:italic>\u03b4<\/jats:italic> \u221241. The tetramethyl carbene complex <jats:bold>3<\/jats:bold> exhibits a similar chemical shift in toluene, but shows a higher frequency signal in acetonitrile arising from the solvent adduct [Ru(IMe<jats:sub>4<\/jats:sub>)<jats:sub>4<\/jats:sub>(MeCN)H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>], <jats:bold>4<\/jats:bold>. The reactivity of <jats:bold>1<\/jats:bold>\u2013<jats:bold>3<\/jats:bold> towards H<jats:sub>2<\/jats:sub> and N<jats:sub>2<\/jats:sub> depends on the size of the N\u2010substituent of the NHC ligand. Thus, <jats:bold>1<\/jats:bold> is unreactive towards both gases, <jats:bold>2<\/jats:bold> reacts with both H<jats:sub>2<\/jats:sub> and N<jats:sub>2<\/jats:sub> only at low temperature and incompletely, while <jats:bold>3<\/jats:bold> affords [Ru(IMe<jats:sub>4<\/jats:sub>)<jats:sub>4<\/jats:sub>(\u03b7<jats:sup>2<\/jats:sup>\u2010H<jats:sub>2<\/jats:sub>)H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] (<jats:bold>7<\/jats:bold>) and [Ru(IMe<jats:sub>4<\/jats:sub>)<jats:sub>4<\/jats:sub>(N<jats:sub>2<\/jats:sub>)H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] (<jats:bold>8<\/jats:bold>) in quantitative yield at room temperature. CO shows no selectivity, reacting with <jats:bold>1<\/jats:bold>\u2013<jats:bold>3<\/jats:bold> to give [Ru(NHC)<jats:sub>4<\/jats:sub>(CO)H][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] (<jats:bold>9<\/jats:bold>\u2013<jats:bold>11<\/jats:bold>). Addition of O<jats:sub>2<\/jats:sub> to solutions of <jats:bold>2<\/jats:bold> and <jats:bold>3<\/jats:bold> leads to rapid oxidation, from which the Ru<jats:sup>III<\/jats:sup> species [Ru(NHC)<jats:sub>4<\/jats:sub>(OH)<jats:sub>2<\/jats:sub>][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] and the Ru<jats:sup>IV<\/jats:sup> oxo chlorido complex [Ru(IEt<jats:sub>2<\/jats:sub>Me<jats:sub>2<\/jats:sub>)<jats:sub>4<\/jats:sub>(O)Cl][BAr<jats:sup>F<\/jats:sup><jats:sub>4<\/jats:sub>] were isolated. DFT calculations reproduce the greater ability of <jats:bold>3<\/jats:bold> to bind small molecules and show relative binding strengths that follow the trend CO \u226b O<jats:sub>2<\/jats:sub> &gt; N<jats:sub>2<\/jats:sub> &gt; H<jats:sub>2<\/jats:sub>.<\/jats:p>","DOI":"10.1002\/chem.200901736","type":"journal-article","created":{"date-parts":[[2009,9,11]],"date-time":"2009-09-11T02:16:30Z","timestamp":1252635390000},"page":"10912-10923","source":"Crossref","is-referenced-by-count":44,"title":["The Influence of N\u2010Heterocyclic Carbenes (NHC) on the Reactivity of [Ru(NHC)<sub>4<\/sub>H]<sup>+<\/sup> With H<sub>2<\/sub>, N<sub>2<\/sub>, CO and O<sub>2<\/sub>"],"prefix":"10.1002","volume":"15","author":[{"given":"Suzanne","family":"Burling","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"L.\u2005Jonas\u2005L.","family":"H\u00e4ller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena","family":"Mas\u2010Marz\u00e1","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aitor","family":"Moreno","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stuart\u2005A.","family":"Macgregor","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mary\u2005F.","family":"Mahon","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paul\u2005S.","family":"Pregosin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael\u2005K.","family":"Whittlesey","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,10,13]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00305a071"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00246a045"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00229a015"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39880000546"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00324a005"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00074a054"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9930003041"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39940001597"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0002420"},{"key":"e_1_2_6_10_2","unstructured":"\u00a0"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020415)114:8<1342::AID-ANGE1342>3.0.CO;2-A"},{"key":"e_1_2_6_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2005.07.012"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2006.10.004"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703883"},{"key":"e_1_2_6_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703883"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/om990054l"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/om034016k"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/om049903h"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0438821"},{"key":"e_1_2_6_20_2","unstructured":"For 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that signals for the Os analogues [Os(dcpe)2H]+and [Os(dippe)2H]+have comparable chemicals shifts to1and2;"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9910001525"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(98)00577-4"},{"key":"e_1_2_6_56_2","unstructured":"Pulsed gradient spin\u2010echo (PGSE) diffusion data for1suggest some but only modest ion pairing (see the Supporting Information Table\u2005S1). In support of this view 1H\u201019F HOESY measurements reveal only weak contacts from the F atoms of the anion to the carbene backbone methyl groups."},{"key":"e_1_2_6_57_2","unstructured":"The [BF4]\u2212salts of1and2were prepared by reaction of the initial purple precipitates with Na[BF4] rather than Na[BArF4]."},{"key":"e_1_2_6_58_2","unstructured":"\u00a0"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/om960113k"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic020082n"},{"key":"e_1_2_6_61_2","unstructured":"Dihydrogen complexes bearing NHC ligands are still relatively rare;"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200303091"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/om049045p"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/om700746h"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/om7010722"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/om800778h"},{"key":"e_1_2_6_67_2","unstructured":"\u00a0"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00221a005"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00008a035"},{"key":"e_1_2_6_70_2","unstructured":"\u00a0"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2008.01.010"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2008.09.005"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/B415562A"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9840000469"},{"key":"e_1_2_6_75_2","unstructured":"2H\u2005NMR spectra were not recorded to confirm whether [Ru(IMe4)4(\u03b72\u2010D2)D][BArF4] was formed."},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9529044"},{"key":"e_1_2_6_77_2","unstructured":"The H\uf8ffH distance is in the range found for [Ru(P\u2013P)2(\u03b72\u2010H2)H]+cations;"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/0010-8545(92)80067-2"},{"key":"e_1_2_6_79_2","unstructured":"reference\u2005[21]."},{"key":"e_1_2_6_80_2","unstructured":"TheT1minof the hydride signal in7was not measured but was recorded for the dinitrogen hydrido species8(374\u2005ms at 238\u2005K 400\u2005MHz). We have used this value and the equation given in reference 21 to determine the H\uf8ffH distance of 0.90\u2005\u00c5."},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00263a024"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic8019827"},{"key":"e_1_2_6_83_2","unstructured":"\u00a0"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00033a009"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00089a029"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/om7010613"},{"key":"e_1_2_6_87_2","unstructured":"\u00a0"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00013a025"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00101a025"},{"key":"e_1_2_6_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/om990669i"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/om040025x"},{"key":"e_1_2_6_92_2","unstructured":"Other examples oftransH\u2010group 8\u2009M\u2010N2geometries;"},{"key":"e_1_2_6_93_2","unstructured":"Fe: reference\u2005[3];"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic971050g"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200590038"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00129a014"},{"key":"e_1_2_6_97_2","unstructured":"\u00a0"},{"key":"e_1_2_6_98_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-328X(86)80134-6"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(97)05439-X"},{"key":"e_1_2_6_100_2","unstructured":"For NMR spectra of [Ru(P\u2013P)2(CO)H]+cations see:"},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1039\/dt9840001203"},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00104a043"},{"key":"e_1_2_6_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic9605579"},{"key":"e_1_2_6_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja065532f"},{"key":"e_1_2_6_105_2","unstructured":"reference\u2005[12]."},{"key":"e_1_2_6_106_2","doi-asserted-by":"publisher","DOI":"10.1007\/b113929"},{"key":"e_1_2_6_107_2","unstructured":"reference\u2005[12];"},{"key":"e_1_2_6_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/om034259c"},{"key":"e_1_2_6_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/om049403o"},{"key":"e_1_2_6_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja982736q"},{"key":"e_1_2_6_111_2","unstructured":"Structures for computation were based upon the crystallographic data detailed above; when such data were unavailable starting geometries were generated by ligand addition to the parent [Ru(NHC)4H]+species or ligand substitution at an appropriate [Ru(NHC)4(L)H]+species."},{"key":"e_1_2_6_112_2","unstructured":"The calculations reproduce high frequency shift seen experimentally for\u03bdCOand\u03bdN\uf8fdN[Ru(dippe)2H(L)]+species compared to their NHC analogues: [Ru(dippe)2H(CO)]+\u03bdCO(calcd)=1950\u2005cm\u22121; [Ru(dippe)2H(N2)]+\u03bdN\uf8fdN=2129\u2005cm\u22121."},{"key":"e_1_2_6_113_2","unstructured":"\u00a0"},{"key":"e_1_2_6_114_2","doi-asserted-by":"publisher","DOI":"10.1039\/DT9760001020"},{"key":"e_1_2_6_115_2","unstructured":"reference\u2005[15];"},{"key":"e_1_2_6_116_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja990523a"},{"key":"e_1_2_6_117_2","doi-asserted-by":"publisher","DOI":"10.1021\/om060078"},{"key":"e_1_2_6_118_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja066411i"},{"key":"e_1_2_6_119_2","unstructured":"\u00a0"},{"key":"e_1_2_6_120_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470132449.ch26"},{"key":"e_1_2_6_121_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1993-25902"},{"key":"e_1_2_6_122_2","unstructured":"We assume that the chloride salt of [Ru(IiPr2Me2)4H]+is formed initially. We made this assumption and carried out the metathesis by adding ten mol equivalents of Na[BArF4]."},{"key":"e_1_2_6_123_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767390000277"},{"key":"e_1_2_6_123_3","unstructured":"SHELXL\u201097 a computer program for crystal structure refinement G.\u2005M. Sheldrick University of G\u00f6ttingen G\u00f6ttingen 1997."},{"key":"e_1_2_6_124_2","unstructured":"Gaussian\u200503 Revision D.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman J.\u2005A. Montgomery \u2005Jr. T. Vreven K.\u2005N. Kudin J.\u2005C. Burant J.\u2005M. Millam S.\u2005S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G.\u2005A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J.\u2005E. Knox H.\u2005P. Hratchian J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski P.\u2005Y. Ayala K. Morokuma G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg V.\u2005G. Zakrzewski S. Dapprich A.\u2005D. Daniels M.\u2005C. Strain O. Farkas D.\u2005K. Malick A.\u2005D. Rabuck K. Raghavachari J.\u2005B. Foresman J.\u2005V. Ortiz Q. Cui A.\u2005G. Baboul S. Clifford J. Cioslowski B.\u2005B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R.\u2005L. Martin D.\u2005J. Fox T. Keith M.\u2005A. Al\u2010Laham C.\u2005Y. Peng A. Nanayakkara M. Challacombe P.\u2005M.\u2005W. Gill B. Johnson W. Chen M.\u2005W. Wong C. Gonzalez J.\u2005A. Pople Gaussian Inc. 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