Steric effects in the proton magnetic resonance spectra of fluorenes and bifluorenyls
High-resolution PMR spectra, measured at 60 MHz over temperatures between −80° and +160° in CS 2, CDCl 3 and (CD 3) 2SO solution, are described for bifluorenyl (IIa), 9-methyl-9,9′-bifluorenyl (IIc), 9-t-butyl-9,9′-bifluorenyl (IIb), five 9-substituted fluorenes, and two 9,9-disubstituted fluorenes....
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| Veröffentlicht in: | Tetrahedron 1970-01, Vol.26 (3), p.911-923 |
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| creator | Bartle, K.D. Bavin, P.M.G. Jones, D.W. L'amie, R. |
| description | High-resolution PMR spectra, measured at 60 MHz over temperatures between −80° and +160° in CS
2, CDCl
3 and (CD
3)
2SO solution, are described for bifluorenyl (IIa), 9-methyl-9,9′-bifluorenyl (IIc), 9-t-butyl-9,9′-bifluorenyl (IIb), five 9-substituted fluorenes, and two 9,9-disubstituted fluorenes. Both 9-(α-naphthyl)-fluorene (Ib) and IIb show coexistence of topographical variants at low temperatures, and comparison of 9-methyl-9-t-butyl- (Ig) and 9-ethyl-9-t-butylfluorene (Ih) spectra with that of 9-t-butylfluorene (If) indicates a reduction in primary proximity deshielding as the size of the second substituent increases. In IIb, the t-butyl resonance is broad at low temperatures, narrows with increasing temperature, and then passes through a remarkable maximum in width of 30 Hz at room temperature before sharpening at high temperatures, when rotation appears to be free about both the 9,9′ and 9-t-bntyl bonds. |
| doi_str_mv | 10.1016/S0040-4020(01)97889-5 |
| format | Article |
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2, CDCl
3 and (CD
3)
2SO solution, are described for bifluorenyl (IIa), 9-methyl-9,9′-bifluorenyl (IIc), 9-t-butyl-9,9′-bifluorenyl (IIb), five 9-substituted fluorenes, and two 9,9-disubstituted fluorenes. Both 9-(α-naphthyl)-fluorene (Ib) and IIb show coexistence of topographical variants at low temperatures, and comparison of 9-methyl-9-t-butyl- (Ig) and 9-ethyl-9-t-butylfluorene (Ih) spectra with that of 9-t-butylfluorene (If) indicates a reduction in primary proximity deshielding as the size of the second substituent increases. In IIb, the t-butyl resonance is broad at low temperatures, narrows with increasing temperature, and then passes through a remarkable maximum in width of 30 Hz at room temperature before sharpening at high temperatures, when rotation appears to be free about both the 9,9′ and 9-t-bntyl bonds.</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/S0040-4020(01)97889-5</identifier><identifier>PMID: 5435930</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Chemical Phenomena ; Chemistry ; Fluorenes - analysis ; Magnetic Resonance Spectroscopy ; Temperature</subject><ispartof>Tetrahedron, 1970-01, Vol.26 (3), p.911-923</ispartof><rights>1970</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c426t-159935b5d9aa8bec47a08665bcf254126ee3411b3f0103d89ef00b946745d1603</citedby><cites>FETCH-LOGICAL-c426t-159935b5d9aa8bec47a08665bcf254126ee3411b3f0103d89ef00b946745d1603</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402001978895$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27903,27904,65308</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/5435930$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bartle, K.D.</creatorcontrib><creatorcontrib>Bavin, P.M.G.</creatorcontrib><creatorcontrib>Jones, D.W.</creatorcontrib><creatorcontrib>L'amie, R.</creatorcontrib><title>Steric effects in the proton magnetic resonance spectra of fluorenes and bifluorenyls</title><title>Tetrahedron</title><addtitle>Tetrahedron</addtitle><description>High-resolution PMR spectra, measured at 60 MHz over temperatures between −80° and +160° in CS
2, CDCl
3 and (CD
3)
2SO solution, are described for bifluorenyl (IIa), 9-methyl-9,9′-bifluorenyl (IIc), 9-t-butyl-9,9′-bifluorenyl (IIb), five 9-substituted fluorenes, and two 9,9-disubstituted fluorenes. Both 9-(α-naphthyl)-fluorene (Ib) and IIb show coexistence of topographical variants at low temperatures, and comparison of 9-methyl-9-t-butyl- (Ig) and 9-ethyl-9-t-butylfluorene (Ih) spectra with that of 9-t-butylfluorene (If) indicates a reduction in primary proximity deshielding as the size of the second substituent increases. In IIb, the t-butyl resonance is broad at low temperatures, narrows with increasing temperature, and then passes through a remarkable maximum in width of 30 Hz at room temperature before sharpening at high temperatures, when rotation appears to be free about both the 9,9′ and 9-t-bntyl bonds.</description><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Fluorenes - analysis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Temperature</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1970</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtLAzEUhYMotVZ_QiEr0cXozUySTlYixRcUXNSuQyZzo5HpTE2mQv-96YNuXV0u59zH-QgZM7hjwOT9HIBDxiGHG2C3alKWKhMnZMi45JngTJ6S4dFyTi5i_AYAxvJiQAaCF0IVMCSLeY_BW4rOoe0j9S3tv5CuQtd3LV2azxb7JAeMXWtaizSuki8Y2jnqmnUXsMVITVvTyh_6TRMvyZkzTcSrQx2RxfPTx_Q1m72_vE0fZ5nluewzJpQqRCVqZUxZoeUTA6WUorIuTwlyiVhwxqrCAYOiLhU6gEpxOeGiZhKKEbne703__qwx9nrpo8WmMS1266hLLvI8L1Uyir3Rhi7GgE6vgl-asNEM9Ban3uHUW1YamN7h1CLNjQ8H1tUS6-PUgV_SH_Y6ppS_HoOO1mPiVPuQOOm68_9c-AOFgoRu</recordid><startdate>19700101</startdate><enddate>19700101</enddate><creator>Bartle, K.D.</creator><creator>Bavin, P.M.G.</creator><creator>Jones, D.W.</creator><creator>L'amie, R.</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19700101</creationdate><title>Steric effects in the proton magnetic resonance spectra of fluorenes and bifluorenyls</title><author>Bartle, K.D. ; Bavin, P.M.G. ; Jones, D.W. ; L'amie, R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-159935b5d9aa8bec47a08665bcf254126ee3411b3f0103d89ef00b946745d1603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1970</creationdate><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Fluorenes - analysis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bartle, K.D.</creatorcontrib><creatorcontrib>Bavin, P.M.G.</creatorcontrib><creatorcontrib>Jones, D.W.</creatorcontrib><creatorcontrib>L'amie, R.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bartle, K.D.</au><au>Bavin, P.M.G.</au><au>Jones, D.W.</au><au>L'amie, R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Steric effects in the proton magnetic resonance spectra of fluorenes and bifluorenyls</atitle><jtitle>Tetrahedron</jtitle><addtitle>Tetrahedron</addtitle><date>1970-01-01</date><risdate>1970</risdate><volume>26</volume><issue>3</issue><spage>911</spage><epage>923</epage><pages>911-923</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>High-resolution PMR spectra, measured at 60 MHz over temperatures between −80° and +160° in CS
2, CDCl
3 and (CD
3)
2SO solution, are described for bifluorenyl (IIa), 9-methyl-9,9′-bifluorenyl (IIc), 9-t-butyl-9,9′-bifluorenyl (IIb), five 9-substituted fluorenes, and two 9,9-disubstituted fluorenes. Both 9-(α-naphthyl)-fluorene (Ib) and IIb show coexistence of topographical variants at low temperatures, and comparison of 9-methyl-9-t-butyl- (Ig) and 9-ethyl-9-t-butylfluorene (Ih) spectra with that of 9-t-butylfluorene (If) indicates a reduction in primary proximity deshielding as the size of the second substituent increases. In IIb, the t-butyl resonance is broad at low temperatures, narrows with increasing temperature, and then passes through a remarkable maximum in width of 30 Hz at room temperature before sharpening at high temperatures, when rotation appears to be free about both the 9,9′ and 9-t-bntyl bonds.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>5435930</pmid><doi>10.1016/S0040-4020(01)97889-5</doi><tpages>13</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Chemical Phenomena Chemistry Fluorenes - analysis Magnetic Resonance Spectroscopy Temperature |
| title | Steric effects in the proton magnetic resonance spectra of fluorenes and bifluorenyls |
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