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<title>UTas ePrints - Synthesis and structural studies of phenyl(iodo)- and methyl(phenyl)palladium(II) complexes of bidentate nitrogen donor ligands</title>
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<meta content="Markies, B.A." name="eprints.creators_name" />
<meta content="Canty, A.J." name="eprints.creators_name" />
<meta content="de Graaf, W." name="eprints.creators_name" />
<meta content="Boersma, J." name="eprints.creators_name" />
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<meta content="Hogerheide, M.P." name="eprints.creators_name" />
<meta content="Smeets, W.J.J." name="eprints.creators_name" />
<meta content="Spek, A.L." name="eprints.creators_name" />
<meta content="van Koten, G." name="eprints.creators_name" />
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<meta content="Synthesis and structural studies of phenyl(iodo)- and methyl(phenyl)palladium(II) complexes of bidentate nitrogen donor ligands" name="eprints.title" />
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<meta content="Palladium; Amine; Oxidative addition; Bipyridine; Crystal structure " name="eprints.keywords" />
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<meta content="Phenylpalladium(II) complexes of the type PdIPh(N-N), with N-N = N,N,N’,N’-tetramethylethylenediamine (tmeda) or 2,2’-bipyridyl (bpy), can be conveniently prepared in 70-95% yield by oxidative addition of iodobenxene to bis(dibenzylideneacetone)palladium(0) in the presence of the appropriate nitrogen donor ligand. The bromo analogues were obtained in only 5-12% yield in this way. The complex PdIPh(tmeda) (la) reacts readily with MeLi to give PdMePh(tmeda) (3) in 88% yield, whereas PdIPh(bpy) (la) gives PdMePh(bpy) (4) and PdMe2(bpy) in varying ratios. The formation of PdMe2(bpy) was found to result from the
synergistic action of lithium iodide and methyllithium. Pure PdMePh(bpy) (4) was obtained in 82% yield via ligand-exchange from PdMePh(tmeda) (3). The crystal structures of PdIPh(N-N) (la, 2a) and PdMePh(N-N) (3, 4) complexes were determined by X-ray diffraction studies. The results show that the phenyl group is always oriented perpendicular to the coordination plane around palladium, with the largest deviation found for 3 (14.3(2)). The Pd-N bond distances in the tmeda complexes (2.127(6)-2.210(3) A) are larger than those in the bpy-coordinated complexes (2.870(8)-2.144(8) A). Similarly, the Pd-C(Me) bond distances (2.5703(8)
and 2.575(l) A) are larger than the Pd-C(Ph) bond distances (1.985(3)-1.996(lO) A)." name="eprints.abstract" />
<meta content="1994" name="eprints.date" />
<meta content="published" name="eprints.date_type" />
<meta content="Journal of Organometallic Chemistry" name="eprints.publication" />
<meta content="482" name="eprints.volume" />
<meta content="1-2" name="eprints.number" />
<meta content="191-199" name="eprints.pagerange" />
<meta content="10.1016/0022-328X(94)88201-0" name="eprints.id_number" />
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of Cambridge, UK 1976." name="eprints.referencetext" />
<meta content="Markies, B.A. and Canty, A.J. and de Graaf, W. and Boersma, J. and Janssen, M.D. and Hogerheide, M.P. and Smeets, W.J.J. and Spek, A.L. and van Koten, G. (1994) Synthesis and structural studies of phenyl(iodo)- and methyl(phenyl)palladium(II) complexes of bidentate nitrogen donor ligands. Journal of Organometallic Chemistry, 482 (1-2). pp. 191-199. ISSN 0022-328X" name="eprints.citation" />
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<meta content="Phenylpalladium(II) complexes of the type PdIPh(N-N), with N-N = N,N,N’,N’-tetramethylethylenediamine (tmeda) or 2,2’-bipyridyl (bpy), can be conveniently prepared in 70-95% yield by oxidative addition of iodobenxene to bis(dibenzylideneacetone)palladium(0) in the presence of the appropriate nitrogen donor ligand. The bromo analogues were obtained in only 5-12% yield in this way. The complex PdIPh(tmeda) (la) reacts readily with MeLi to give PdMePh(tmeda) (3) in 88% yield, whereas PdIPh(bpy) (la) gives PdMePh(bpy) (4) and PdMe2(bpy) in varying ratios. The formation of PdMe2(bpy) was found to result from the
synergistic action of lithium iodide and methyllithium. Pure PdMePh(bpy) (4) was obtained in 82% yield via ligand-exchange from PdMePh(tmeda) (3). The crystal structures of PdIPh(N-N) (la, 2a) and PdMePh(N-N) (3, 4) complexes were determined by X-ray diffraction studies. The results show that the phenyl group is always oriented perpendicular to the coordination plane around palladium, with the largest deviation found for 3 (14.3(2)). The Pd-N bond distances in the tmeda complexes (2.127(6)-2.210(3) A) are larger than those in the bpy-coordinated complexes (2.870(8)-2.144(8) A). Similarly, the Pd-C(Me) bond distances (2.5703(8)
and 2.575(l) A) are larger than the Pd-C(Ph) bond distances (1.985(3)-1.996(lO) A)." name="DC.description" />
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<h1 class="ep_tm_pagetitle">Synthesis and structural studies of phenyl(iodo)- and methyl(phenyl)palladium(II) complexes of bidentate nitrogen donor ligands</h1>
<p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Markies, B.A.</span> and <span class="person_name">Canty, A.J.</span> and <span class="person_name">de Graaf, W.</span> and <span class="person_name">Boersma, J.</span> and <span class="person_name">Janssen, M.D.</span> and <span class="person_name">Hogerheide, M.P.</span> and <span class="person_name">Smeets, W.J.J.</span> and <span class="person_name">Spek, A.L.</span> and <span class="person_name">van Koten, G.</span> (1994) <xhtml:em>Synthesis and structural studies of phenyl(iodo)- and methyl(phenyl)palladium(II) complexes of bidentate nitrogen donor ligands.</xhtml:em> Journal of Organometallic Chemistry, 482 (1-2). pp. 191-199. ISSN 0022-328X</p><p style="margin-bottom: 1em" class="not_ep_block"></p><table style="margin-bottom: 1em" class="not_ep_block"><tr><td valign="top" style="text-align:center"><a href="http://eprints.utas.edu.au/2876/1/JOMC19942C_191.pdf"><img alt="[img]" src="http://eprints.utas.edu.au/style/images/fileicons/application_pdf.png" class="ep_doc_icon" border="0" /></a></td><td valign="top"><a href="http://eprints.utas.edu.au/2876/1/JOMC19942C_191.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />959Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input accept-charset="utf-8" value="3849" name="docid" type="hidden" /><div class=""><input value="Request a copy" name="_action_null" class="ep_form_action_button" onclick="return EPJS_button_pushed( '_action_null' )" type="submit" /> </div></form></td></tr></table><p style="margin-bottom: 1em" class="not_ep_block">Official URL: <a href="http://dx.doi.org/10.1016/0022-328X(94)88201-0">http://dx.doi.org/10.1016/0022-328X(94)88201-0</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">Phenylpalladium(II) complexes of the type PdIPh(N-N), with N-N = N,N,N’,N’-tetramethylethylenediamine (tmeda) or 2,2’-bipyridyl (bpy), can be conveniently prepared in 70-95% yield by oxidative addition of iodobenxene to bis(dibenzylideneacetone)palladium(0) in the presence of the appropriate nitrogen donor ligand. The bromo analogues were obtained in only 5-12% yield in this way. The complex PdIPh(tmeda) (la) reacts readily with MeLi to give PdMePh(tmeda) (3) in 88% yield, whereas PdIPh(bpy) (la) gives PdMePh(bpy) (4) and PdMe2(bpy) in varying ratios. The formation of PdMe2(bpy) was found to result from the
synergistic action of lithium iodide and methyllithium. Pure PdMePh(bpy) (4) was obtained in 82% yield via ligand-exchange from PdMePh(tmeda) (3). The crystal structures of PdIPh(N-N) (la, 2a) and PdMePh(N-N) (3, 4) complexes were determined by X-ray diffraction studies. The results show that the phenyl group is always oriented perpendicular to the coordination plane around palladium, with the largest deviation found for 3 (14.3(2)). The Pd-N bond distances in the tmeda complexes (2.127(6)-2.210(3) A) are larger than those in the bpy-coordinated complexes (2.870(8)-2.144(8) A). Similarly, the Pd-C(Me) bond distances (2.5703(8)
and 2.575(l) A) are larger than the Pd-C(Ph) bond distances (1.985(3)-1.996(lO) A).</p></div><table style="margin-bottom: 1em" cellpadding="3" class="not_ep_block" border="0"><tr><th valign="top" class="ep_row">Item Type:</th><td valign="top" class="ep_row">Article</td></tr><tr><th valign="top" class="ep_row">Additional Information:</th><td valign="top" class="ep_row">The definitive version is available at http://www.sciencedirect.com
</td></tr><tr><th valign="top" class="ep_row">Keywords:</th><td valign="top" class="ep_row">Palladium; Amine; Oxidative addition; Bipyridine; Crystal structure </td></tr><tr><th valign="top" class="ep_row">Subjects:</th><td valign="top" class="ep_row"><a href="http://eprints.utas.edu.au/view/subjects/259901.html">250000 Chemical Sciences > 259900 Other Chemical Sciences > 259901 Organometallic Chemistry</a></td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2876</td></tr><tr><th valign="top" class="ep_row">Deposited By:</th><td valign="top" class="ep_row"><span class="ep_name_citation"><span class="person_name">Prof Allan J Canty</span></span></td></tr><tr><th valign="top" class="ep_row">Deposited On:</th><td valign="top" class="ep_row">04 Jan 2008 14:48</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">09 Jan 2008 02:30</td></tr><tr><th valign="top" class="ep_row">ePrint Statistics:</th><td valign="top" class="ep_row"><a target="ePrintStats" href="/es/index.php?action=show_detail_eprint;id=2876;">View statistics for this ePrint</a></td></tr></table><p align="right">Repository Staff Only: <a href="http://eprints.utas.edu.au/cgi/users/home?screen=EPrint::View&eprintid=2876">item control page</a></p>
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