Experimental Evidence of Phosphine Oxide Generation in Solution and Trapping by Ruthenium Complexes
2011; Wiley; Volume: 123; Issue: 23 Linguagem: Inglês
10.1002/ange.201100822
ISSN1521-3757
AutoresDmitry G. Yakhvarov, Maria Caporali, Luca Gonsalvi, Shamil K. Latypov, Vincenzo Mirabello, И. Х. Ризванов, Оleg G. Sinyashin, Piero Stoppioni, Maurizio Peruzzini,
Tópico(s)Analytical chemistry methods development
ResumoAngewandte ChemieVolume 123, Issue 23 p. 5482-5485 Zuschrift Experimental Evidence of Phosphine Oxide Generation in Solution and Trapping by Ruthenium Complexes† Correction(s) for this article Berichtigung: Experimental Evidence of Phosphine Oxide Generation in Solution and Trapping by Ruthenium Complexes Dmitry Yakhvarov, Maria Caporali, Luca Gonsalvi, Shamil Latypov, Vincenzo Mirabello, Ildar Rizvanov, Oleg Sinyashin, Piero Stoppioni, Maurizio Peruzzini, Volume 124Issue 11Angewandte Chemie pages: 2584-2584 First Published online: March 7, 2012 Dr. Dmitry Yakhvarov, Corresponding Author Dr. Dmitry Yakhvarov [email protected] A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253 Dmitry Yakhvarov, A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253 Maurizio Peruzzini, Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Maria Caporali, Dr. Maria Caporali Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Luca Gonsalvi, Dr. Luca Gonsalvi Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Shamil Latypov, Dr. Shamil Latypov A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253Search for more papers by this authorVincenzo Mirabello, Vincenzo Mirabello Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Ildar Rizvanov, Dr. Ildar Rizvanov A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253Search for more papers by this authorProf. Oleg Sinyashin, Prof. Oleg Sinyashin A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253Search for more papers by this authorProf. Piero Stoppioni, Prof. Piero Stoppioni Dipartimento Chimica, Università degli Studi di Firenze, Via della Lastruccia, 3-50019 Sesto Fiorentino (Italy)Search for more papers by this authorDr. Maurizio Peruzzini, Corresponding Author Dr. Maurizio Peruzzini [email protected] Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.it Dmitry Yakhvarov, A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253 Maurizio Peruzzini, Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this author Dr. Dmitry Yakhvarov, Corresponding Author Dr. Dmitry Yakhvarov [email protected] A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253 Dmitry Yakhvarov, A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253 Maurizio Peruzzini, Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Maria Caporali, Dr. Maria Caporali Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Luca Gonsalvi, Dr. Luca Gonsalvi Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Shamil Latypov, Dr. Shamil Latypov A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253Search for more papers by this authorVincenzo Mirabello, Vincenzo Mirabello Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this authorDr. Ildar Rizvanov, Dr. Ildar Rizvanov A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253Search for more papers by this authorProf. Oleg Sinyashin, Prof. Oleg Sinyashin A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253Search for more papers by this authorProf. Piero Stoppioni, Prof. Piero Stoppioni Dipartimento Chimica, Università degli Studi di Firenze, Via della Lastruccia, 3-50019 Sesto Fiorentino (Italy)Search for more papers by this authorDr. Maurizio Peruzzini, Corresponding Author Dr. Maurizio Peruzzini [email protected] Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.it Dmitry Yakhvarov, A.E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Arbuzov str., 8, 420088 Kazan (Russian Federation), Fax: (+7) 843-273-2253 Maurizio Peruzzini, Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino (Italy), Fax: (+39) 055-522-5203 http://www.iccom.cnr.itSearch for more papers by this author First published: 28 April 2011 https://doi.org/10.1002/ange.201100822Citations: 16 † The authors thank NATO-RUSSIA collaborative linkage grant CPB.NR.NRCLG 983375 and CNR-RAS bilateral agreement for funding short-term stages. Financial support by MIUR (Italy) through PRIN2007, Russian Foundation for Basic Research (RFBR 09-03-00933-a), Russian Science Support Fund, and by “FIRENZE HYDROLAB”, a project sponsored by the ECRF, is also gratefully acknowledged. COST Action CM0802 “PhoSciNet” is also thanked. Thermphos Intl BV (Vlissingen, NL) is thanked for a generous loan of P4. We thank Dr. P. Barbaro (ICCOM CNR) for assistance in recording some 2D-NMR experiments. Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Phosphinoxid (H3PO), die erste definierte Verbindung von Phosphor in der Oxidationsstufe −1, konnte in Lösung elektrochemisch aus weißem Phosphor hergestellt werden (siehe Bild). H3PO wurde durch Lösungs-NMR-Spektroskopie als freies Molekül charakterisiert und nach Tautomerisierung zu phosphiniger Säure H2P(OH) als Ligand in Ruthenium(II)-Komplexen isoliert. Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description ange_201100822_sm_miscellaneous_information.pdf595.7 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1D. E. C. Corbridge, Phosphorus: an Outline of its Chemistry, Biochemistry and Technology, 5th ed., Elsevier SA, Amsterdam, 1995. Google Scholar 2Phosphorus compounds are both rare and ubiquitous in the universe, PO being the most important interstellar compound and the main repository of phosphorus in the cosmos. See: L. R. Thorne, V. G. Anicich, S. S. Prasad, W. T. Huntress, ;Jr., APJ 1984, 280, 139–143; 10.1086/161977 CASWeb of Science®Google ScholarE. Maciá, Chem. Soc. Rev. 2005, 34, 691–701, and references therein. 10.1039/b416855k CASPubMedWeb of Science®Google Scholar 3P. A. Hamilton, T. P. Murrells, J. Chem. Soc. Faraday Trans. 2 1985, 81, 1531–1541. 10.1039/f29858101531 CASWeb of Science®Google Scholar 4R. Withnall, L. Andrews, J. Phys. Chem. 1987, 91, 784–791; 10.1021/j100288a008 CASWeb of Science®Google ScholarR. Withnall, L. Andrews, J. Phys. Chem. 1988, 92, 4610–4619. 10.1021/j100327a012 CASWeb of Science®Google Scholar 5D. A. Kayser, B. S. Ault, J. Phys. Chem. A 2003, 107, 6500–6505. 10.1021/jp022692e CASWeb of Science®Google Scholar 6 6aM. W. Schmidt, M. S. Gordon, Can. J. Chem. 1985, 63, 1609–1615; 10.1139/v85-271 CASWeb of Science®Google Scholar 6bM. W. Schmidt, M. S. Gordon, J. Am. Chem. Soc. 1985, 107, 1922–1930; 10.1021/ja00293a021 CASWeb of Science®Google Scholar 6cM. W. Schmidt, S. Yabushita, M. S. Gordon, J. Phys. Chem. 1984, 88, 382–389; 10.1021/j150647a012 CASWeb of Science®Google Scholar 6dE. Magnusson, Aust. J. Chem. 1986, 39, 735–745. 10.1071/CH9860735 CASWeb of Science®Google Scholar 7C. J. Cramer, C. E. Dykstra, S. E. Denmark, Chem. Phys. Lett. 1987, 136, 17–21. 10.1016/0009-2614(87)87290-1 CASWeb of Science®Google Scholar 8S. S. Wesolowski, N. R. Brinkmann, E. F. Valeev, H. F. Schaefer, M. P. Repasky, W. L. Jorgensen, J. Chem. Phys. 2002, 116, 112–122. 10.1063/1.1418440 CASWeb of Science®Google Scholar 9Y.-L. Zhao, J. W. Flora, W. D. Thweatt, S. L. Garrison, C. Gonzalez, K. N. Houk, M. Marquez, Inorg. Chem. 2009, 48, 1223–1231. 10.1021/ic801917a CASPubMedWeb of Science®Google Scholar 10N. Ya. Shandrinov, A. P. Tomilov, Electrokhimiya 1968, 4, 237–239. CASGoogle Scholar 11The electrochemical hydrogenation of P4 to PH3 has been studied in detail. In alkaline solution (≤15 % NaOH), the yield of PH3 may reach ca. 80 % using a lead cathode at temperatures above 70 °C. See Ref. [10] and H. Tsuchiya, A. Otsuji, Yu. Sakagami (Heisei), Jpn. Pat. 01139781A2 19890601, 1989. Google Scholar 12A careful calibration of the integral intensities in the 1H NMR spectrum according to the weights of PH3 (15.1 %) and H3PO2 (16.1 %) taken from the 31P{1H} NMR spectra also allowed the number of protons attached to phosphorus to be evaluated directly from the signal at δ=−17.55 ppm, confirming the presence of three protons per phosphorus. Google Scholar 13The facile disproportionation of H3PO and the unavoidable presence of both PH3 and H3PO2 prevented us to get a more defined chemicophysical characterization of the phosphine oxide. Nonetheless, strong IR bands in the reaction mixture at about 1250 cm−1 were assigned to PO stretching modes, although it was not be possible to discriminate between H3PO and H3PO2 contributions. MS data for H3PO could not be obtained owing to its quick decomposition under the working condition of the mass spectrometer. Google Scholar 14M. Caporali, L. Gonsalvi, A. Rossin, M. Peruzzini, Chem. Rev. 2010, 110, 4178–4235; 10.1021/cr900349u CASPubMedWeb of Science®Google ScholarB. M. Cossairt, N. A. Piro, C. C. Cummins, Chem. Rev. 2010, 110, 4164–4177; 10.1021/cr9003709 CASPubMedWeb of Science®Google ScholarM. Scheer, G. Balász, A. Seitz, Chem. Rev. 2010, 110, 4236–4256. 10.1021/cr100010e CASPubMedWeb of Science®Google Scholar 15M. Di Vaira, P. Frediani, S. Seniori Costantini, M. Peruzzini, P. Stoppioni, Dalton Trans. 2005, 2234–2236. 10.1039/b504795a CASPubMedWeb of Science®Google Scholar 16 16aP. Barbaro, M. Di Vaira, S. Seniori Costantini, M. Peruzzini, P. Stoppioni, Angew. Chem. 2008, 120, 4497–4499; 10.1002/ange.200800723 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 4425–4427; 10.1002/anie.200800723 CASPubMedWeb of Science®Google ScholarP. Barbaro, M. Di Vaira, S. Seniori Costantini, M. Peruzzini, P. Stoppioni, Inorg. Chem. 2009, 48, 1091–1096; 10.1021/ic801859z CASPubMedWeb of Science®Google Scholar 16bM. Di Vaira, M. Peruzzini, P. Stoppioni, C. R. Chim. 2010, 13, 935–942. 10.1016/j.crci.2010.07.004 CASWeb of Science®Google Scholar 17D. N. Akbayeva, M. Di Vaira, S. Seniori Costantini, M. Peruzzini, P. Stoppioni, Dalton Trans. 2006, 389–395. 10.1039/B510479C CASPubMedWeb of Science®Google Scholar 18A. Romerosa, M. Saoud, T. Campos-Malpartida, C. Lidrissi, M. Serrano-Ruiz, M. Peruzzini, J. A. Garrido, F. García-Maroto, Eur. J. Inorg. Chem. 2007, 2803–2812. 10.1002/ejic.200601177 CASWeb of Science®Google Scholar 19S. Bolaño, L. Gonsalvi, F. Zanobini, F. Vizza, V. Bertolasi, A. Romerosa, M. Peruzzini, J. Mol. Catal. A 2004, 224, 61–70. 10.1016/j.molcata.2004.06.030 CASWeb of Science®Google Scholar 20As the electrogenerated solution of H3PO was always contaminated by variable amounts of PH3 and H3PO2, the formation of 4 and 5 was always accompanied by variable quantities of compounds [CpRu(tppms)2(PH3)]PF6 (4 b), [CpRu(tppms)2{PH(OH)2}]PF6 (4 c), [CpRu(pta)(CH3CN)(PH3)]PF6 (5 b), and [CpRu(pta)(CH3CN){PH(OH)2}]PF6 (5 c), respectively. These complexes were identified by comparison of the NMR data with those obtained from their independent syntheses from the reaction of 2 and 3 with PH3 and H3PO2, respectively (Supporting Information). The presence of these contaminants has hampered the growth of crystals suitable for a crystallographic study for either 4 or 5. Google Scholar 21P. Barbaro, M. Di Vaira, M. Peruzzini, S. Seniori Costantini, P. Stoppioni, Chem. Eur. J. 2007, 13, 6682–6690. 10.1002/chem.200601846 CASPubMedWeb of Science®Google Scholar 22D. G. Yakhvarov, E. A. Trofimova, O. G. Sinyashin, Russ. Pat. 85903, C25B3/12, 2009. Priority 09.04.2009; Publ. 20.08.2009. Google Scholar Citing Literature Volume123, Issue23May 27, 2011Pages 5482-5485 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
Referência(s)