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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Self-Assembly of Square-Planar Halide Complexes of Trimethylphosphine-Stabilized Diphenyl-Arsenium, -Stibenium, and -Bismuthenium Hexafluorophosphates*

J. Wolfram Wielandt A B , Simon Petrie A , Nathan L. Kilah A C , Anthony C. Willis A , Rian D. Dewhurst A D , Ferdinand Belaj B , Andreas Orthaber B , Robert Stranger A E and S. Bruce Wild A E
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, College of Physical and Mathematical Sciences, Australian National University, Canberra, ACT 2601, Australia.

B Institut für Chemie, Karl-Franzens-Universität Graz, 8010 Graz, Austria.

C School of Physical Sciences – Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia.

D Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

E Corresponding authors. Email: rob.stranger@anu.edu.au; bruce.wild@anu.edu.au

Australian Journal of Chemistry 69(5) 524-532 https://doi.org/10.1071/CH15701
Submitted: 3 November 2015  Accepted: 26 December 2015   Published: 28 January 2016

Abstract

Square-planar halide complexes in which four trimethylphosphine-stabilized diphenyl-stibenium or -bismuthenium ions surround a central halide ion in discrete centrosymmetrical structures of C4h symmetry have been isolated and their structures determined by X-ray crystallography. The structures are stabilized by electrostatic interactions between the halide ion and four positively charged trimethylphosphine-stabilized diphenyl-stibenium or -bismuthenium ions, as well as four edge-to-face phenyl–phenyl embraces above and below the plane containing the nine main group elements. The parent halide-free trimethylphosphine-stabilized diphenyl-arsenium, -stibenium, and -bismuthenium hexaflurophosphate complexes have also been prepared and structurally characterized.


References

[1]  M. S. Vickers, P. D. Beer, Chem. Soc. Rev. 2007, 36, 211.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVKltLY%3D&md5=4013167681ad2ad2ca80692220300521CAS | 17264924PubMed |

[2]  R. Vilar, Angew. Chem. Int. Ed. 2003, 42, 1460.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjtlyhtbc%3D&md5=29814d90194a03720869db2895460485CAS |

[3]  X. Yang, C. B. Knobler, M. F. Hawthorne, Angew. Chem. Int. Ed. Engl. 1991, 30, 1507.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  Z. Zheng, C. B. Knobler, M. F. Hawthorne, J. Am. Chem. Soc. 1995, 117, 5105.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXltlykur0%3D&md5=b1b0ca8d8ec863d66510203d570931f4CAS |

[5]  B. Hasenknopf, J.-M. Lehn, B. O. Kneisel, G. Baum, D. Fenske, Angew. Chem. Int. Ed. Engl. 1996, 35, 1838.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xls1Gqtbo%3D&md5=a71d0a2ea60a542e9340197c7ef4c553CAS |

[6]  T. Dubé, S. Conoci, S. Gambarotta, G. P. A. Yap, G. Vasapollo, Angew. Chem. Int. Ed. 1999, 38, 3657.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  R. Wang, H. D. Selby, H. Liu, M. D. Carducci, T. Jin, Z. Zheng, J. W. Anthis, R. J. Staples, Inorg. Chem. 2002, 41, 278.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XlslSl&md5=5b17217eff4ed4c4b92fd3afcb87020aCAS | 11800615PubMed |

[8]  R. Wang, Z. Zheng, T. Jin, R. J. Staples, Angew. Chem. Int. Ed. 1999, 38, 1813.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXktVCnur0%3D&md5=086247a2150a7988069b2f060a71d37aCAS |

[9]  S.-T. Cheng, E. Doxiadi, R. Vilar, A. J. P. White, D. J. Williams, J. Chem. Soc., Dalton Trans. 2001, 2239.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlsVWnt7w%3D&md5=8b7dd44ef7d59f62476eb36c1403b296CAS |

[10]  R. Vilar, D. M. P. Mingos, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. 1998, 37, 1258.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXjs1egt7g%3D&md5=9297c6b80c4d3c46a74b2da6779ac442CAS |

[11]  R. Vilar, D. M. P. Mingos, A. J. P. White, D. J. Williams, Chem. Commun. 1999, 229.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  P. D. Beer, M. R. Sambrook, D. Curiel, Chem. Commun. 2006, 2105.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkslentL8%3D&md5=313ccffbb5203b08c565e37dd58df501CAS |

[13]  R. Vilar, in Supramolecular Assembly via Hydrogen Bonds II (Ed. D. M. P. Mingos) 2004, Vol. 111, pp. 85–137 (Springer: Berlin).

[14]  N. L. Kilah, M. D. Wise, C. J. Serpell, A. L. Thompson, N. G. White, K. E. Christensen, P. D. Beer, J. Am. Chem. Soc. 2010, 132, 11893.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXpvVartb4%3D&md5=473364698cca3f5d42a1f0a73ee6f3acCAS | 20687599PubMed |

[15]  G. T. Spence, P. D. Beer, Acc. Chem. Res. 2013, 46, 571.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhsleqt7nL&md5=768653eaf27d1845c58c4fc3e5fd75feCAS | 23190374PubMed |

[16]  J. W. Wielandt, N. L. Kilah, A. C. Willis, S. B. Wild, Chem. Commun. 2006, 3679.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XoslGkt7s%3D&md5=d45d3705ea7d2a880b62c963c32ff0bcCAS |

[17]  G. G. Briand, N. Burford, T. S. Cameron, W. Kwiatkowski, J. Am. Chem. Soc. 1998, 120, 11374.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmslKjs7w%3D&md5=36492fd4ea49569f6a3f4e631fd0ab79CAS |

[18]  H. J. Breunig, M. Denker, K. H. Ebert, J. Chem. Soc., Chem. Commun. 1994, 875.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlvFWrtLo%3D&md5=9572cd0ece1ca8522d7442fedcc2d8c4CAS |

[19]  H. J. Breunig, M. Denker, R. E. Schulz, E. Lork, Z. Anorg. Allg. Chem. 1998, 624, 81.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXkt1KqsA%3D%3D&md5=3b9ef80be739595ec3fb073c44c6d180CAS |

[20]  H. Althaus, H. J. Breunig, E. Lork, Chem. Commun. 1999, 1971.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmt1CqsL4%3D&md5=c07b29dce459bf9be2e69aacb97ba8aeCAS |

[21]  N. J. Hill, W. Levason, G. Reid, J. Chem. Soc., Dalton Trans. 2002, 1188.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhslClsLs%3D&md5=63b700293a2ceed2ee00798226f1c9b6CAS |

[22]  H. J. Breunig, I. Ghesner, Adv. Organomet. Chem. 2003, 49, 95.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXovFGku7g%3D&md5=a2375cd1482e97b89f069116b6d85d2bCAS |

[23]  W. Levason, G. Reid, in Comprehensive Coordination Chemistry II (Eds J. A. McCleverty, T. J. Meyer) 2004, pp. 465–544 (Elsevier: New York, NY).

[24]  S. Petrie, R. Stranger, A. D. Rae, A. C. Willis, X. Zhou, S. B. Wild, Organometallics 2006, 25, 164.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1Gkt7bI&md5=f08ecf71d9694eb7a6ec94942d5eee7dCAS |

[25]  S. S. Chitnis, N. Burford, R. McDonald, M. J. Ferguson, Inorg. Chem. 2014, 53, 5359.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXmvFCis78%3D&md5=e15b7f8342cfb651180d65d28fb5ce4bCAS | 24773563PubMed |

[26]  J. M. F. Braddock, G. E. Coates, J. Chem. Soc. 1961, 3208.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF38XkvVegtLw%3D&md5=30675cbc428dd8a005959a1259974407CAS |

[27]  G. E. Coates, J. G. Livingstone, Chem. Ind. 1958, 1366.
         | 1:CAS:528:DyaG1MXksV2iug%3D%3D&md5=764bcd360cfd07d5cdebf2c0202fdc0fCAS |

[28]  E. Conrad, N. Burford, R. McDonald, M. J. Ferguson, Inorg. Chem. 2008, 47, 2952.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjsVWhsb4%3D&md5=3930c9c518807086e909fac7cc3ac898CAS | 18345596PubMed |

[29]  K. A. Porter, A. C. Willis, J. Zank, S. B. Wild, Inorg. Chem. 2002, 41, 6380.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XotlCjsL0%3D&md5=d8bd5802fef39c955ef68c1ffe7c3691CAS | 12444781PubMed |

[30]  N. Burford, P. J. Ragogna, K. Sharp, R. McDonald, M. J. Ferguson, Inorg. Chem. 2005, 44, 9453.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFKltr3J&md5=5cb50ba746fbaa1db09b35272f00ed44CAS | 16323932PubMed |

[31]  N. L. Kilah, S. Petrie, R. Stranger, J. W. Wielandt, A. C. Willis, S. B. Wild, Organometallics 2007, 26, 6106.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1elsLrF&md5=0fd6b34c03af86bfa3812d49ace1ddaeCAS |

[32]  N. L. Kilah, M. L. Weir, S. B. Wild, Dalton Trans. 2008, 2480.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlsVGlurw%3D&md5=0a5ad7c9413c8cc73ab69ff85546a2e2CAS | 18461204PubMed |

[33]  A. P. M. Robertson, N. Burford, R. McDonald, M. J. Ferguson, Angew. Chem. Int. Ed. 2014, 53, 3480.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXjtVGls74%3D&md5=85b32db068119afbc71358b4eb9b1b2fCAS |

[34]  S. S. Chitnis, N. Burford, J. J. Weigand, R. McDonald, Angew. Chem. Int. Ed. 2015, 54, 7828.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXpt12gtbs%3D&md5=04f8ec0d046a626b3f12831e2bf80a65CAS |

[35]  S. S. Chitnis, A. P. M. Robertson, N. Burford, J. J. Weigand, R. Fischer, Chem. Sci. 2015, 6, 2559.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhvFKntb0%3D&md5=7e5b79e03273681d3049148f4e940196CAS |

[36]  S. S. Chitnis, B. Peters, E. Conrad, N. Burford, R. McDonald, M. J. Ferguson, Chem. Commun. 2011, 12331.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVaqsLfN&md5=19a49a597930b3090677b1a8e59e849fCAS |

[37]  E. Conrad, N. Burford, U. Werner-Zwanziger, R. McDonald, M. J. Ferguson, Chem. Commun. 2010, 2465.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjs1Gmtr0%3D&md5=acb3e91ca342602fac287ac37399bc3dCAS |

[38]  S. S. Chitnis, N. Burford, Dalton Trans. 2015, 44, 17.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhslGrt7vM&md5=3096cc9258876eb5ab43ea57a6a6a37cCAS | 25352363PubMed |

[39]  A. P. M. Robertson, P. A. Gray, N. Burford, Angew. Chem. Int. Ed. 2014, 53, 6050.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXos1aksrs%3D&md5=1907fcfa555e91df51c812d6768128e7CAS |

[40]  B. Cordero, V. Gomez, A. E. Platero-Prats, M. Reves, J. Echeverria, E. Cremades, F. Barragan, S. Alvarez, Dalton Trans. 2008, 2832.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlvFKrurY%3D&md5=d725719cbe0c5cd48ea762b3565e7313CAS | 18478144PubMed |

[41]  S. Alvarez, Dalton Trans. 2013, 8617.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXot1emur8%3D&md5=434165c73acd3e454da995107b53db71CAS | 23632803PubMed |

[42]  POVRAY 3.6 2004 (Persistence of Vision Pty Ltd: Melbourne, Australia).

[43]  F. M. Bickelhaupt, E. J. Baerends, in Reviews in Computational Chemistry (Eds K. B. Lipkowitz, D. B. Boyd) 2000, pp. 1–86 (Wiley-VCH: New York, NY).

[44]  W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals 2003 (Butterworth–Heinemann: Burlington, MA).

[45]  W. J. Pope, E. E. Turner, J. Chem. Soc. Trans. 1920, 117, 1447.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaB3MXotVWh&md5=67dc2f606fcbd36d8010694a539c2c86CAS |

[46]  M. Nunn, D. B. Sowerby, D. M. Wesolek, J. Organomet. Chem. 1983, 251, c45.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXlvFGisLk%3D&md5=3bf5d592b933fa288eda9be85ae512dbCAS |

[47]  F. Challenger, C. F. Allpress, J. Chem. Soc. Trans. 1915, 107, 16.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaC2MXmvVCj&md5=fbc2286cbc3cfc8c5c67139791fc2483CAS |

[48]  M. L. Luetkens, A. P. Sattelberger, H. H. Murray, J. D. Basil, J. P. Fackler, Inorg. Synth. 1990, 28, 305.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXotF2rsQ%3D%3D&md5=5539ff02ac3c06964619d624b2bf0f18CAS |

[49]  A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Cryst. 1994, 27, 435.
         | Crossref | GoogleScholarGoogle Scholar |

[50]  P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Cryst. 2003, 36, 1487.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXptFekt78%3D&md5=a9d7db80ae806851ebb7b50839017d55CAS |

[51]  G. M. Sheldrick, SHELXS-97: Program for Crystal Structure Solution 1997 (University of Göttingen: Göttingen, Germany).

[52]  G. M. Sheldrick, SHELXL-97: Program for the Refinement of Crystal Structures 1997 (University of Göttingen: Göttingen, Germany).

[53]  L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnt1KgsLg%3D&md5=73cc226b6a448ce22eb035dbadda41dcCAS |

[54]  E. J. Baerends, J. Autschbach, A. Bérces, C. Bo, P. M. Boerrigter, L. Cavallo, D. P. Chong, L. Deng, R. M. Dickson, D. E. Ellis, L. Fan, T. H. Fischer, C. Fonseca Guerra, S. J. A. van Gisbergen, J. A. Groeneveld, O. V. Gritsenko, M. Gruning, F. E. Harris, P. van den Hoek, H. Jacobsen, G. van Kessel, F. Kootstra, E. van Lenthe, D. A. McCormack, V. P. Osinga, S. Patchkovskii, P. H. T. Philipsen, D. Post, C. C. Pye, W. Ravenek, P. Ros, P. R. T. Schipper, G. Schreckenbach, J. G. Snijders, M. Sola, M. Swart, D. Swerhone, G. te Velde, P. Vernooijs, L. Versluis, O. Visser, E. van Wezenbeek, G. Wiesenekker, S. K. Wolff, T. K. Woo, T. Ziegler, Amsterdam Density Functional 2004 (Scientific Computing & Modelling NV: Amsterdam).

[55]  C. Fonseca Guerra, J. G. Snijders, G. te Velde, E. J. Baerends, Theor. Chem. Acc. 1998, 99, 391.
         | Crossref | GoogleScholarGoogle Scholar |

[56]  G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. F. Guerra, S. J. A. Van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjtlGntrw%3D&md5=69ae957349e8738dfc0d0570eec66d65CAS |

[57]  J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXht1Gns7o%3D&md5=d3bf3af88893c60749d96d5d1f065d41CAS |

[58]  L. Versluis, T. Ziegler, J. Chem. Phys. 1988, 88, 322.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXhvFejtr0%3D&md5=962533eba7624372cfe0bc375ae53c43CAS |

[59]  K. Kitaura, K. Morokuma, Int. J. Quantum Chem. 1976, 10, 325.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE28Xhs12rtbs%3D&md5=06120e99845522e33810061559b492c4CAS |

[60]  K. Morokuma, J. Chem. Phys. 1971, 55, 1236.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXkvVSnsLY%3D&md5=c1c268085ed35ee227014d2f98b9af57CAS |

[61]  T. Ziegler, A. Rauk, Inorg. Chem. 1979, 18, 1755.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXks1ejsL0%3D&md5=9dc400f805354196653d60996e2bd122CAS |

[62]  T. Ziegler, A. Rauk, Inorg. Chem. 1979, 18, 1558.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXkt1SmtLw%3D&md5=bb33e7cb957aeda2265cf667fc867aafCAS |