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Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles</title> <script type="text/javascript" src="http://eprints.utas.edu.au/javascript/auto.js"><!-- padder --></script> <style type="text/css" media="screen">@import url(http://eprints.utas.edu.au/style/auto.css);</style> <style type="text/css" media="print">@import url(http://eprints.utas.edu.au/style/print.css);</style> <link rel="icon" href="/images/eprints/favicon.ico" type="image/x-icon" /> <link rel="shortcut icon" href="/images/eprints/favicon.ico" type="image/x-icon" /> <link rel="Top" href="http://eprints.utas.edu.au/" /> <link rel="Search" href="http://eprints.utas.edu.au/cgi/search" /> <meta content="Canty, A.J." name="eprints.creators_name" /> <meta content="Lee, C.V." name="eprints.creators_name" /> <meta content="allan.canty@utas.edu.au" name="eprints.creators_id" /> <meta content="" name="eprints.creators_id" /> <meta content="article" name="eprints.type" /> <meta content="2008-01-15T00:40:14Z" name="eprints.datestamp" /> <meta content="2008-01-15T00:40:14Z" name="eprints.lastmod" /> <meta content="show" name="eprints.metadata_visibility" /> <meta content="Interaction of Methylmercury(II) with N-Substituted Pyrazoles. Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles" name="eprints.title" /> <meta content="pub" name="eprints.ispublished" /> <meta content="250200" name="eprints.subjects" /> <meta content="restricted" name="eprints.full_text_status" /> <meta content="N-Substituted pyrazoles (L) form complexes [MeHgL]NO, for which 2J(1H-199Hg) decreases with increasing basicity of L in a very similar manner to that observed for closely related N-substituted imidazole complexes. The relationships differ from that for complexes of pyridines and suggest that for ligands of similar log KH (pKa of LH+ in 50% dioxane-water) the N-substituted imidazoles and pyrazoles are better sigma donors toward MeHg(II) than pyridines. The complexes [MeHgL]NO3 [L = N-(2-pyridyl)pyrazole and bis(N-pyrazoly1)methane] have the ligands chelated to MeHg(II) when in methanol." name="eprints.abstract" /> <meta content="1982" name="eprints.date" /> <meta content="published" name="eprints.date_type" /> <meta content="Organometallics" name="eprints.publication" /> <meta content="1" name="eprints.volume" /> <meta content="8" name="eprints.number" /> <meta content="1063-1066" name="eprints.pagerange" /> <meta content="10.1021/om00068a012" name="eprints.id_number" /> <meta content="TRUE" name="eprints.refereed" /> <meta content="0276-7333" name="eprints.issn" /> <meta content="http://dx.doi.org/10.1021/om00068a012" name="eprints.official_url" /> <meta content=" (1) Canty, A. J.; Marker, A. Znorg. Chem. 1976,15,425. (2) Canty, A. J.; Barron, P.; Healy, P. C. J. Organomet. Chem. 1979, (3) Canty, A. J.; Chaichit, N.; Gatehouse, B. M.; George, E. E.; Hay- (4) Canty, A. J.; Tobias, R. S. Znorg. Chem. 1979, 18, 413. (5) Canty, A. J.; Lee, C. V. Inorg. Chim. Acta 1981,54, L205. (6) Canty, A. J.; Lee, C. V.; Chaichit, N.; Gatehouse, B. M. Acta 179, 447. hurst, G. Inorg. Chem. 1981,20, 2414. Crystallogr., Sect. B 1982, B38, 743. (7) "Vogel's Textbook of Practical Organic Chemistry", 4th ed.; revised by Fumise, B. S., Hannaford, A. J., Rogers, V., Smith, P. W. G., Tatchell, A. R.; 1978. (8) Grimmett, M. R.; Lim, K. H. R.; Weavers, R. T. A u t . J. Chem. 1979,32,2203. (9) Finar, I. L.; Lord, G. H. J. Chem. SOC. 1967, 3314. (10) Knorr, L. Justus Liebigs Ann. Chem. 1894,279, 232. (11) Knorr, L. Chem. Ber. 1896,28, 714. (12) Reid, W.; Muhle, G. Jwtus Liebigs Ann. Chem. 1962, 656,119. (13) Jones, R. G. J. Am. Chem. SOC. 1949, 71, 3994. (14) Anet, F. A. L.; Sudmeier, J. L. J. Magn. Reson. 1969, 124. Henneike, H. F. J. Am. Chem. SOC. 1972,94, 5945. (15) Simpson, R. B. J. Am. Chem. SOC. 1961,83,4711. (16) Geier, G.; Erni, I.; Steiner, R. Helu. Chin. Acta 1979,60, 9. (17) Emi, I. W. Ph.D. Dissertation, E.T.H. Zurich, 1977. (18) Flabenstein, D. L. Acc. Chem. Res. 1978,11, 100. (19) Anderegg, G. Helu. Chim. Acta 1974,57, 1340. (20) Canty, A. J.; Chaichit, N.; Gatehouse, B. M.; George, E. E. Inorg. Chem. 1981,20,4293. (21) Canty, A. J.; Hayhurst, G.; Chaichit, N.; Gatehouse, B. M. J. Chem. Soc., Chem. Commun. 1980, 316. (22) Canty, A. J.; Chaichit, N.; Gatehouse, B. M. Acta Crystallogr. (23) Canty, A. J.; Gatehouse, B. M. J. Chem. SOC., Dalton Trans. 1976, (24) Scheffold, R. Helu. Chim. Acta 1969, 52, 56. (25) Libich, S.; Rabenetein, D. L.; Anal. Chem. 1973,45, 118. (26) Beletakaya, I. P.; Fedin, E. I.; Fyodorov, L. A.; Kvasov, B. A.; (27) Evans, D. F.; Ridout, P. M.; Wharf, I. J. Chem. Soc. A 1968,2127. (28) Sytama, L. F.; Kline, R. J. J. Organomet. Chem. 1973, 54, 15. (29) Fedorov, L. A.; Fedin, E. I.; Kvasov, B. A.; Beletakaya, I. P. J. (30) Barlin, G. B.; Perrin, D. D. Q. Rev., Chem. SOC. 1966, 20, 75. Sect. (31) Benesch, R. E.; Benesch, R. J. Am. Chem. SOC. 1966, 77, 5877. (32) Rabenstein, D. L.; Fairhust, M. T. J. Am. Chem. SOC. 1976,97, 2086. (33) Rabenetein, D. L.; Ozubko, R.; Libich, S.; Evans, C. A.; Fairhust, M. T.; Suvanprakorn, C. J. Coord. Chem. 1974,3, 263. (34) Sugiura, Y.; Hojo, Y.; Tamai, Y.; Tanaka, H. J. Am. Chem. SOC. 1976,98,2339. Sugiura, Y.; Tamai, Y.; Tanaka, H. Bioinorg. Chem. 1978, 167, 167. (35) Arnold, A. P.; Canty, A. J. Znorg. Chim. Acta 1981,55, 171. (36)S illBn, L. G. Spec. PubL-Chem. SOC.19 71, No. 25, Suppl. 1. (37)C larke, K.; Rothwell, K. J. Chem. SOC.19 69, 1885." name="eprints.referencetext" /> <meta content="Canty, A.J. and Lee, C.V. (1982) Interaction of Methylmercury(II) with N-Substituted Pyrazoles. Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles. Organometallics, 1 (8). pp. 1063-1066. ISSN 0276-7333" name="eprints.citation" /> <meta content="http://eprints.utas.edu.au/2866/1/Organomet1982_2C_1063.pdf" name="eprints.document_url" /> <link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /> <meta content="Interaction of Methylmercury(II) with N-Substituted Pyrazoles. Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles" name="DC.title" /> <meta content="Canty, A.J." name="DC.creator" /> <meta content="Lee, C.V." name="DC.creator" /> <meta content="250200 Inorganic Chemistry" name="DC.subject" /> <meta content="N-Substituted pyrazoles (L) form complexes [MeHgL]NO, for which 2J(1H-199Hg) decreases with increasing basicity of L in a very similar manner to that observed for closely related N-substituted imidazole complexes. The relationships differ from that for complexes of pyridines and suggest that for ligands of similar log KH (pKa of LH+ in 50% dioxane-water) the N-substituted imidazoles and pyrazoles are better sigma donors toward MeHg(II) than pyridines. The complexes [MeHgL]NO3 [L = N-(2-pyridyl)pyrazole and bis(N-pyrazoly1)methane] have the ligands chelated to MeHg(II) when in methanol." name="DC.description" /> <meta content="1982" name="DC.date" /> <meta content="Article" name="DC.type" /> <meta content="PeerReviewed" name="DC.type" /> <meta content="application/pdf" name="DC.format" /> <meta content="http://eprints.utas.edu.au/2866/1/Organomet1982_2C_1063.pdf" name="DC.identifier" /> <meta content="http://dx.doi.org/10.1021/om00068a012" name="DC.relation" /> <meta content="Canty, A.J. and Lee, C.V. (1982) Interaction of Methylmercury(II) with N-Substituted Pyrazoles. Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles. Organometallics, 1 (8). pp. 1063-1066. 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border: solid 1px #ccc; padding: 3px"><tr> <td align="left"><a href="http://eprints.utas.edu.au/cgi/users/home">Login</a> | <a href="http://eprints.utas.edu.au/cgi/register">Create Account</a></td> <td align="right" style="white-space: nowrap"> <form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/search" style="display:inline"> <input class="ep_tm_searchbarbox" size="20" type="text" name="q" /> <input class="ep_tm_searchbarbutton" value="Search" type="submit" name="_action_search" /> <input type="hidden" name="_order" value="bytitle" /> <input type="hidden" name="basic_srchtype" value="ALL" /> <input type="hidden" name="_satisfyall" value="ALL" /> </form> </td> </tr></table></td></tr> <tr> <td class="toplinks"><!-- InstanceBeginEditable name="content" --> <div align="center"> <table width="720" class="ep_tm_main"><tr><td align="left"> <h1 class="ep_tm_pagetitle">Interaction of Methylmercury(II) with N-Substituted Pyrazoles. Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles</h1> <p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Canty, A.J.</span> and <span class="person_name">Lee, C.V.</span> (1982) <xhtml:em>Interaction of Methylmercury(II) with N-Substituted Pyrazoles. Sigma-Donor Ability of Pyridines, Imidazoles, and Pyrazoles.</xhtml:em> Organometallics, 1 (8). pp. 1063-1066. ISSN 0276-7333</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/2866/1/Organomet1982_2C_1063.pdf"><img alt="[img]" src="http://eprints.utas.edu.au/style/images/fileicons/application_pdf.png" border="0" class="ep_doc_icon" /></a></td><td valign="top"><a href="http://eprints.utas.edu.au/2866/1/Organomet1982_2C_1063.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />497Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input value="4087" name="docid" accept-charset="utf-8" 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/10.1021/om00068a012">http://dx.doi.org/10.1021/om00068a012</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">N-Substituted pyrazoles (L) form complexes [MeHgL]NO, for which 2J(1H-199Hg) decreases with increasing basicity of L in a very similar manner to that observed for closely related N-substituted imidazole complexes. The relationships differ from that for complexes of pyridines and suggest that for ligands of similar log KH (pKa of LH+ in 50% dioxane-water) the N-substituted imidazoles and pyrazoles are better sigma donors toward MeHg(II) than pyridines. The complexes [MeHgL]NO3 [L = N-(2-pyridyl)pyrazole and bis(N-pyrazoly1)methane] have the ligands chelated to MeHg(II) when in methanol.</p></div><table style="margin-bottom: 1em" border="0" cellpadding="3" class="not_ep_block"><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">Subjects:</th><td valign="top" class="ep_row"><a href="http://eprints.utas.edu.au/view/subjects/250200.html">250000 Chemical Sciences > 250200 Inorganic Chemistry</a></td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2866</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">15 Jan 2008 11:40</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">15 Jan 2008 11:40</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=2866;">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=2866">item control page</a></p> </td></tr></table> </div> <!-- InstanceEndEditable --></td> </tr> <tr> <td><!-- #BeginLibraryItem "/Library/footer_eprints.lbi" --> <table width="795" border="0" align="left" cellpadding="0" class="footer"> <tr valign="top"> <td colspan="2"><div align="center"><a href="http://www.utas.edu.au">UTAS home</a> | <a href="http://www.utas.edu.au/library/">Library home</a> | <a href="/">ePrints home</a> | <a href="/contact.html">contact</a> | <a href="/information.html">about</a> | <a href="/view/">browse</a> | <a href="/perl/search/simple">search</a> | <a href="/perl/register">register</a> | <a href="/perl/users/home">user area</a> | <a href="/help/">help</a></div><br /></td> </tr> <tr><td colspan="2"><p><img src="/images/eprints/footerline.gif" width="100%" height="4" /></p></td></tr> <tr valign="top"> <td width="68%" class="footer">Authorised by the University Librarian<br /> © University of Tasmania ABN 30 764 374 782<br /> <a href="http://www.utas.edu.au/cricos/">CRICOS Provider Code 00586B</a> | <a href="http://www.utas.edu.au/copyright/copyright_disclaimers.html">Copyright & Disclaimers</a> | <a href="http://www.utas.edu.au/accessibility/index.html">Accessibility</a> | <a href="http://eprints.utas.edu.au/feedback/">Site Feedback</a> </td> <td width="32%"><div align="right"> <p align="right" class="NoPrint"><a href="http://www.utas.edu.au/"><img src="http://www.utas.edu.au/shared/logos/unioftasstrip.gif" alt="University of Tasmania Home Page" width="260" height="16" border="0" align="right" /></a></p> <p align="right" class="NoPrint"><a href="http://www.utas.edu.au/"><br /> </a></p> </div></td> </tr> <tr valign="top"> <td><p> </p></td> <td><div align="right"><span class="NoPrint"><a href="http://www.eprints.org/software/"><img src="/images/eprintslogo.gif" alt="ePrints logo" width="77" height="29" border="0" align="bottom" /></a></span></div></td> </tr> </table> <!-- #EndLibraryItem --> <div align="center"></div></td> </tr> </table> </body> </html>