{19}$F NMR Studies on 8,9-Dehydro-2-adamantyl and 2,4-Dehydro-5-homoadamantyl Cations
To probe the geometrical effects of cyclopropyl moiety on the stabilization of an adjacent cation center,
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| Veröffentlicht in: | Bulletin of the Korean Chemical Society 1989, Vol.10 (2), p.132-133 |
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| container_end_page | 133 |
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| container_issue | 2 |
| container_start_page | 132 |
| container_title | Bulletin of the Korean Chemical Society |
| container_volume | 10 |
| creator | Shim, Jae-Chul Nam, Ghil-Soo Kim, Kyong-Tae Shin, Jung-Hyu |
| description | To probe the geometrical effects of cyclopropyl moiety on the stabilization of an adjacent cation center, |
| format | Article |
| fullrecord | <record><control><sourceid>kisti</sourceid><recordid>TN_cdi_kisti_ndsl_JAKO198913464453270</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>JAKO198913464453270</sourcerecordid><originalsourceid>FETCH-kisti_ndsl_JAKO1989134644532703</originalsourceid><addsrcrecordid>eNqNyrsKwjAYQOEgChbtO2TQrYHm1vYfpSqiqOBlLpFUGmwTMHUo4ru7iK5OZ_hODwWUMSASBPRREDPJCYNEDFHovbnEkvM0STkE6Pyk8Jos8W57wMf2oU3psbM4i4DMy6rTd0cYUVo1yrZdjZXVmEXia5JUrnE_z1VrnPVjNLiq2pfhpyM0XS5O-YrcjG9NYbWvi_Vss6eQAeUiEUJylsb83-8NZCo-QQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>{19}$F NMR Studies on 8,9-Dehydro-2-adamantyl and 2,4-Dehydro-5-homoadamantyl Cations</title><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Shim, Jae-Chul ; Nam, Ghil-Soo ; Kim, Kyong-Tae ; Shin, Jung-Hyu</creator><creatorcontrib>Shim, Jae-Chul ; Nam, Ghil-Soo ; Kim, Kyong-Tae ; Shin, Jung-Hyu</creatorcontrib><description>To probe the geometrical effects of cyclopropyl moiety on the stabilization of an adjacent cation center, <$^{19}F$ chemical shift of 2-p-fluorophenyl-8,9-dehydro-2-adamantyl cation (3) was compared with that of 5-p-fluorophenyl-2,4-dehydro-5-homoadamantyl cation (4). Difference between the <$^{19}F$ chemical shift of 8,9-dehydro-2-adamantyl cation 3 and that of 2,4-dehydro-5-adamantyl cation 4 is 5.1 ppm (${\Delta}{\Delta}{\delta}$). We conclude, therefore, that ion 3 is about 3.82 kcal more stadble than ion 4 of which rigid carbon skeleton requires significant distortion of the cyclopropane ring from the ideal bisected conformation. The energy difference between these cations can be calculated by Taft-Relationship$^8$ on the basis of <$^{19}F$ chemical shift.</description><identifier>ISSN: 0253-2964</identifier><identifier>EISSN: 1229-5949</identifier><language>kor</language><ispartof>Bulletin of the Korean Chemical Society, 1989, Vol.10 (2), p.132-133</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,4010</link.rule.ids></links><search><creatorcontrib>Shim, Jae-Chul</creatorcontrib><creatorcontrib>Nam, Ghil-Soo</creatorcontrib><creatorcontrib>Kim, Kyong-Tae</creatorcontrib><creatorcontrib>Shin, Jung-Hyu</creatorcontrib><title>{19}$F NMR Studies on 8,9-Dehydro-2-adamantyl and 2,4-Dehydro-5-homoadamantyl Cations</title><title>Bulletin of the Korean Chemical Society</title><addtitle>Bulletin of the Korean chemical society</addtitle><description>To probe the geometrical effects of cyclopropyl moiety on the stabilization of an adjacent cation center, <$^{19}F$ chemical shift of 2-p-fluorophenyl-8,9-dehydro-2-adamantyl cation (3) was compared with that of 5-p-fluorophenyl-2,4-dehydro-5-homoadamantyl cation (4). Difference between the <$^{19}F$ chemical shift of 8,9-dehydro-2-adamantyl cation 3 and that of 2,4-dehydro-5-adamantyl cation 4 is 5.1 ppm (${\Delta}{\Delta}{\delta}$). We conclude, therefore, that ion 3 is about 3.82 kcal more stadble than ion 4 of which rigid carbon skeleton requires significant distortion of the cyclopropane ring from the ideal bisected conformation. The energy difference between these cations can be calculated by Taft-Relationship$^8$ on the basis of <$^{19}F$ chemical shift.</description><issn>0253-2964</issn><issn>1229-5949</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>JDI</sourceid><recordid>eNqNyrsKwjAYQOEgChbtO2TQrYHm1vYfpSqiqOBlLpFUGmwTMHUo4ru7iK5OZ_hODwWUMSASBPRREDPJCYNEDFHovbnEkvM0STkE6Pyk8Jos8W57wMf2oU3psbM4i4DMy6rTd0cYUVo1yrZdjZXVmEXia5JUrnE_z1VrnPVjNLiq2pfhpyM0XS5O-YrcjG9NYbWvi_Vss6eQAeUiEUJylsb83-8NZCo-QQ</recordid><startdate>1989</startdate><enddate>1989</enddate><creator>Shim, Jae-Chul</creator><creator>Nam, Ghil-Soo</creator><creator>Kim, Kyong-Tae</creator><creator>Shin, Jung-Hyu</creator><scope>JDI</scope></search><sort><creationdate>1989</creationdate><title>{19}$F NMR Studies on 8,9-Dehydro-2-adamantyl and 2,4-Dehydro-5-homoadamantyl Cations</title><author>Shim, Jae-Chul ; Nam, Ghil-Soo ; Kim, Kyong-Tae ; Shin, Jung-Hyu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-kisti_ndsl_JAKO1989134644532703</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>kor</language><creationdate>1989</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shim, Jae-Chul</creatorcontrib><creatorcontrib>Nam, Ghil-Soo</creatorcontrib><creatorcontrib>Kim, Kyong-Tae</creatorcontrib><creatorcontrib>Shin, Jung-Hyu</creatorcontrib><collection>KoreaScience</collection><jtitle>Bulletin of the Korean Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shim, Jae-Chul</au><au>Nam, Ghil-Soo</au><au>Kim, Kyong-Tae</au><au>Shin, Jung-Hyu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>{19}$F NMR Studies on 8,9-Dehydro-2-adamantyl and 2,4-Dehydro-5-homoadamantyl Cations</atitle><jtitle>Bulletin of the Korean Chemical Society</jtitle><addtitle>Bulletin of the Korean chemical society</addtitle><date>1989</date><risdate>1989</risdate><volume>10</volume><issue>2</issue><spage>132</spage><epage>133</epage><pages>132-133</pages><issn>0253-2964</issn><eissn>1229-5949</eissn><abstract>To probe the geometrical effects of cyclopropyl moiety on the stabilization of an adjacent cation center, <$^{19}F$ chemical shift of 2-p-fluorophenyl-8,9-dehydro-2-adamantyl cation (3) was compared with that of 5-p-fluorophenyl-2,4-dehydro-5-homoadamantyl cation (4). Difference between the <$^{19}F$ chemical shift of 8,9-dehydro-2-adamantyl cation 3 and that of 2,4-dehydro-5-adamantyl cation 4 is 5.1 ppm (${\Delta}{\Delta}{\delta}$). We conclude, therefore, that ion 3 is about 3.82 kcal more stadble than ion 4 of which rigid carbon skeleton requires significant distortion of the cyclopropane ring from the ideal bisected conformation. The energy difference between these cations can be calculated by Taft-Relationship$^8$ on the basis of <$^{19}F$ chemical shift.</abstract><oa>free_for_read</oa></addata></record> |
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| ispartof | Bulletin of the Korean Chemical Society, 1989, Vol.10 (2), p.132-133 |
| issn | 0253-2964 1229-5949 |
| language | kor |
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| title | {19}$F NMR Studies on 8,9-Dehydro-2-adamantyl and 2,4-Dehydro-5-homoadamantyl Cations |
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