{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T14:23:38Z","timestamp":1790778218487,"version":"4.1.0"},"reference-count":171,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2017,10,12]],"date-time":"2017-10-12T00:00:00Z","timestamp":1507766400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004543","name":"China Scholarship Council","doi-asserted-by":"publisher","award":["Ph.D. grant"],"award-info":[{"award-number":["Ph.D. grant"]}],"id":[{"id":"10.13039\/501100004543","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004794","name":"Centre National de la Recherche Scientifique","doi-asserted-by":"publisher","award":["half a teaching sabbatical"],"award-info":[{"award-number":["half a teaching sabbatical"]}],"id":[{"id":"10.13039\/501100004794","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-11-BS07-016-01"],"award-info":[{"award-number":["ANR-11-BS07-016-01"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2017,11,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The coordination chemistry of a priori weakly <jats:italic>\u03c3<\/jats:italic>\u2010donating nitroaromatic phosphines is addressed through a series of nitro\u2010substituted (<jats:italic>N<\/jats:italic>\u2010phenyl\u2010benzimidazol\u20101\u2010yl)diphenylphosphines in Rh<jats:sup>I<\/jats:sup> complexes. From a set of seven such phosphines L=L<jats:sub>xyz<\/jats:sub><jats:sup>(\u2032)<\/jats:sup> (<jats:italic>x<\/jats:italic>, <jats:italic>y<\/jats:italic>, <jats:italic>z<\/jats:italic>=0 or 1=number of NO<jats:sub>2<\/jats:sub> substituents at the 5, 6 and N\u2010Ph <jats:italic>para<\/jats:italic> positions, respectively), including the non\u2010nitrated parent L<jats:sub>000<\/jats:sub> and its dicationic N\u2010methyl counterpart L<jats:sub>000<\/jats:sub>\u2032, three LRhCl(COD) and seven L<jats:sub>2<\/jats:sub>RhCl(CO) complexes have been obtained in 72\u201395\u2009% yield. Despite of a <jats:italic>cis<\/jats:italic> orientation of the L and CO ligands, the C=O IR stretching frequency <jats:italic>\u03bd<\/jats:italic><jats:sub>CO<\/jats:sub> varies in the expected sense, from 1967\u00b11\u2005cm<jats:sup>\u22121<\/jats:sup> for L<jats:sub>xy0<\/jats:sub> to 1978\u00b11\u2005cm<jats:sup>\u22121<\/jats:sup> for L<jats:sub>xy1<\/jats:sub>, and 2005\u2005cm<jats:sup>\u22121<\/jats:sup> for L<jats:sub>000<\/jats:sub>\u2032. The <jats:sup>103<\/jats:sup>Rh NMR chemical shift <jats:italic>\u03b4<\/jats:italic><jats:sub>Rh<\/jats:sub> varies from \u2212288\u2005ppm for L<jats:sub>000<\/jats:sub> to \u2212316\u00b11\u2005ppm for L<jats:sub>10z<\/jats:sub> or L<jats:sub>01z<\/jats:sub>, and \u2212436\u2005ppm for L<jats:sub>000<\/jats:sub>\u2032. The <jats:italic>\u03bd<\/jats:italic><jats:sub>CO<\/jats:sub> and <jats:italic>\u03b4<\/jats:italic><jats:sub>Rh<\/jats:sub> probes thus reveal moderate but systematic variations, and act as \u201corthogonal\u201d spectroscopic indicators of the presence of nitro groups on the N\u2010Ph group and the benzimidazole core, respectively. For the dicationic ligand L<jats:sub>000<\/jats:sub>\u2032, a tight electrostatic sandwiching of the Rh\u2010Cl bond by the benzimidazole moities is evidenced by X\u2010ray crystallography (RhCl<jats:sup><jats:italic>\u03b4<\/jats:italic>\u2212<\/jats:sup>\u22c5\u22c5\u22c5CN<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup> \u22483.01\u2005\u00c5). Along with the LRhCl(CO) complexes, dinuclear side\u2010products (\u03bc\u2010CO)(RhClL)<jats:sub>2<\/jats:sub> were also obtained in low spectroscopic yield: for the dinitro ligand L=L<jats:sub>011<\/jats:sub>, a unique 1:6.7 clathrate structure, with dichloromethane as solvate, is also revealed by X\u2010ray crystallography.<\/jats:p>","DOI":"10.1002\/asia.201701078","type":"journal-article","created":{"date-parts":[[2017,8,28]],"date-time":"2017-08-28T06:28:49Z","timestamp":1503901729000},"page":"2845-2856","source":"Crossref","is-referenced-by-count":6,"title":["The Forgotten Nitroaromatic Phosphines as Weakly Donating P\u2010ligands: An <i>N<\/i>\u2010Aryl<b>\u2010benzimidazolyl Series in RhCl(CO) Complexes<\/b>"],"prefix":"10.1002","volume":"12","author":[{"given":"Chongwei","family":"Zhu","sequence":"first","affiliation":[{"name":"CNRS LCC (Laboratoire de Chimie de Coordination)  205 route de Narbonne, BP44099 31077 Toulouse Cedex 4 France"},{"name":"Universit\u00e9 de Toulouse  UPS, ICT-FR 2599 31062 Toulouse Cedex 9 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emmanuel","family":"Gras","sequence":"additional","affiliation":[{"name":"CNRS LCC (Laboratoire de Chimie de Coordination)  205 route de Narbonne, BP44099 31077 Toulouse Cedex 4 France"},{"name":"Universit\u00e9 de Toulouse  UPS, ICT-FR 2599 31062 Toulouse Cedex 9 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carine","family":"Duhayon","sequence":"additional","affiliation":[{"name":"CNRS LCC (Laboratoire de Chimie de Coordination)  205 route de Narbonne, BP44099 31077 Toulouse Cedex 4 France"},{"name":"Universit\u00e9 de Toulouse  UPS, ICT-FR 2599 31062 Toulouse Cedex 9 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francis","family":"Lacassin","sequence":"additional","affiliation":[{"name":"CNRS LCC (Laboratoire de Chimie de Coordination)  205 route de Narbonne, BP44099 31077 Toulouse Cedex 4 France"},{"name":"Universit\u00e9 de Toulouse  UPS, ICT-FR 2599 31062 Toulouse Cedex 9 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiuling","family":"Cui","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences Huaqiao University  Xiamen 361021 P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4491-6390","authenticated-orcid":false,"given":"Remi","family":"Chauvin","sequence":"additional","affiliation":[{"name":"CNRS LCC (Laboratoire de Chimie de Coordination)  205 route de Narbonne, BP44099 31077 Toulouse Cedex 4 France"},{"name":"Universit\u00e9 de Toulouse  UPS, ICT-FR 2599 31062 Toulouse Cedex 9 France"},{"name":"Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences Huaqiao University  Xiamen 361021 P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,10,12]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2015.07.018"},{"key":"e_1_2_8_2_1","unstructured":"\u00a0"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60146c"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000165"},{"key":"e_1_2_8_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000165"},{"key":"e_1_2_8_5_2","volume-title":"Top. Organomet. 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D."},{"key":"e_1_2_8_53_1","unstructured":"\u00a0"},{"key":"e_1_2_8_54_2","first-page":"297","volume":"9","author":"Stachlewska-Wroblowa A.","year":"1961","journal-title":"Bull. Acad. Pol. Sci. Ser. Sci. Chim."},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19660990219"},{"key":"e_1_2_8_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19711040426"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/j39690001314"},{"key":"e_1_2_8_58_2","doi-asserted-by":"publisher","DOI":"10.1080\/03086648508077667"},{"key":"e_1_2_8_59_1","unstructured":"DFT calculations at the B3PW91\/6-31G(d p) level without solvent correction (vacuum) using the Firefly software (see SI):"},{"key":"e_1_2_8_60_2","unstructured":"A.\u2005A. Granovsky Firefly version 8 (http:\/\/classic.chem.msu.su:gran:firefly:index.html) which is partially based on the GAMESS (US) source code;"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540141112"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00512a034"},{"key":"e_1_2_8_63_1","unstructured":"\u00a0"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1087354"},{"key":"e_1_2_8_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo4012199"},{"key":"e_1_2_8_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol303448j"},{"key":"e_1_2_8_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA08858E"},{"key":"e_1_2_8_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4DT03477E"},{"key":"e_1_2_8_69_1","unstructured":"Model nitroaryl-phosphine ligands in RhII RuIIor FeIIcomplexes have however been calculated at the DFT level of theory:"},{"key":"e_1_2_8_70_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-004-0611-2"},{"key":"e_1_2_8_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic062171w"},{"key":"e_1_2_8_72_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00706-015-1433-8"},{"key":"e_1_2_8_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.6b00471"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.197619761119"},{"key":"e_1_2_8_75_1","unstructured":"\u00a0"},{"key":"e_1_2_8_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070225a"},{"key":"e_1_2_8_77_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.12.018"},{"key":"e_1_2_8_78_1","unstructured":"\u00a0"},{"key":"e_1_2_8_79_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01850-5"},{"key":"e_1_2_8_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(02)02014-4"},{"key":"e_1_2_8_81_1","unstructured":"For recent examples in the aryl-heteroaryl series see:"},{"key":"e_1_2_8_82_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.07.082"},{"key":"e_1_2_8_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm4018375"},{"key":"e_1_2_8_84_1","unstructured":"\u00a0"},{"key":"e_1_2_8_85_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29890000573"},{"key":"e_1_2_8_86_2","first-page":"489","volume":"257","author":"Bartoli G.","year":"1989","journal-title":"NATO ASI Ser. 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Noteworthy the Buchwald\u2032s procedure from1\u2009b cand 4-iodonitrobenzene was found much less efficient giving2\u2009fand2\u2009gin 25\u2009% and 12\u2009% yield respectively."},{"key":"e_1_2_8_99_1","doi-asserted-by":"crossref","first-page":"71","DOI":"10.3998\/ark.5550190.0003.111","author":"Wang A. L.","year":"2002","journal-title":"ARKIVOC"},{"key":"e_1_2_8_100_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1291150"},{"key":"e_1_2_8_101_1","unstructured":"CCDC\u20051496156\u2005(3\u2009b) 1496157\u2005(3\u2009c) 1496158\u2005(3\u2009f) 1496159\u2005(3\u2009e) 1496162\u2005(5\u2009a) 1496160\u2005(5\u2009b) 1496161\u2005(5\u2009c) 1496163\u2005(5\u2009f) 1496164\u2005(5\u2009g) 1496165\u2005(5\u2009a\u2032) and 1496166\u2005(6\u2009f) contain the supplementary crystallographic data for this paper. 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