A norbornenyl derivative with through-space ketone π-interaction

A norbornenyl derivative with through-space ketone π-interaction

The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­dodeca‐9‐en‐anti‐11‐yl p‐bromo­benzoate, C19H17BrO3, con­sists of norbornene with an anti‐p‐bromo­benzoate substituent at the methano bridge and an exo‐fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2000-11, Vol.56 (11), p.1377-1379
Hauptverfasser: Lloyd, Barry A., Arif, Atta M., Allred, Evan L.
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Organic compounds
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1379
container_issue 11
container_start_page 1377
container_title Acta crystallographica. Section C, Crystal structure communications
container_volume 56
creator Lloyd, Barry A.
Arif, Atta M.
Allred, Evan L.
description The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­dodeca‐9‐en‐anti‐11‐yl p‐bromo­benzoate, C19H17BrO3, con­sists of norbornene with an anti‐p‐bromo­benzoate substituent at the methano bridge and an exo‐fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially pyramidalized. Through‐space ketone π‐inter­action is probably responsible for the low solvolysis rate of the anti‐11‐chloride derivative.
doi_str_mv 10.1107/S0108270100011185
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72411750</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72411750</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4550-939492637c8d3736be8672cd1f45a8c813c0726f08b63109961895b4985916853</originalsourceid><addsrcrecordid>eNqFkMuO0zAUQC0EoqXwAWxQJCR2nvG149eyVJAZTTXDowixshzXoWbSpGOnU7rjD_mlSWlUFizY3Lu459wXQi-BnAEQef6ZAFFU9pEQAFD8ERqDIARzyfVjND6U8aE-Qs9S-tFTlFL2FI0OtmSEj9F0mjVtLNvY-GZfZ0sfw73twr3PdqFbZd0qttvvK5w21vns1ndt47Pfv3BoOh-t60LbPEdPKlsn_2LIE_Tl_bvF7ALPb4rL2XSOXc45wZrpXFPBpFNLJpkovRKSuiVUObfKKWCOSCoqokrBgGgtQGle5lpxDUJxNkFvjn03sb3b-tSZdUjO17VtfLtNRtIcQHLSg3AEXWxTir4ymxjWNu4NEHO43Pzzt955NTTflmu__GsMj-qB1wNgk7N1FW3jQjpxqt8YaE-pI7ULtd__f66Zfpu9vQL-Z2t8VEPq_M-TauOtEZJJbr5eFyYvFqr48DE3n9gDj16Raw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72411750</pqid></control><display><type>article</type><title>A norbornenyl derivative with through-space ketone π-interaction</title><source>Crystallography Journals Online</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Lloyd, Barry A. ; Arif, Atta M. ; Allred, Evan L.</creator><creatorcontrib>Lloyd, Barry A. ; Arif, Atta M. ; Allred, Evan L.</creatorcontrib><description>The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­dodeca‐9‐en‐anti‐11‐yl p‐bromo­benzoate, C19H17BrO3, con­sists of norbornene with an anti‐p‐bromo­benzoate substituent at the methano bridge and an exo‐fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially pyramidalized. Through‐space ketone π‐inter­action is probably responsible for the low solvolysis rate of the anti‐11‐chloride derivative.</description><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S0108270100011185</identifier><identifier>PMID: 11077305</identifier><identifier>CODEN: ACSCEE</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: Munksgaard International Publishers</publisher><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; Organic compounds ; Physics ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Acta crystallographica. Section C, Crystal structure communications, 2000-11, Vol.56 (11), p.1377-1379</ispartof><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4550-939492637c8d3736be8672cd1f45a8c813c0726f08b63109961895b4985916853</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1107%2FS0108270100011185$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1107%2FS0108270100011185$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,3975,27911,27912,45561,45562</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=810912$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11077305$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lloyd, Barry A.</creatorcontrib><creatorcontrib>Arif, Atta M.</creatorcontrib><creatorcontrib>Allred, Evan L.</creatorcontrib><title>A norbornenyl derivative with through-space ketone π-interaction</title><title>Acta crystallographica. Section C, Crystal structure communications</title><addtitle>Acta Cryst. C</addtitle><description>The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­dodeca‐9‐en‐anti‐11‐yl p‐bromo­benzoate, C19H17BrO3, con­sists of norbornene with an anti‐p‐bromo­benzoate substituent at the methano bridge and an exo‐fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially pyramidalized. Through‐space ketone π‐inter­action is probably responsible for the low solvolysis rate of the anti‐11‐chloride derivative.</description><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0108-2701</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqFkMuO0zAUQC0EoqXwAWxQJCR2nvG149eyVJAZTTXDowixshzXoWbSpGOnU7rjD_mlSWlUFizY3Lu459wXQi-BnAEQef6ZAFFU9pEQAFD8ERqDIARzyfVjND6U8aE-Qs9S-tFTlFL2FI0OtmSEj9F0mjVtLNvY-GZfZ0sfw73twr3PdqFbZd0qttvvK5w21vns1ndt47Pfv3BoOh-t60LbPEdPKlsn_2LIE_Tl_bvF7ALPb4rL2XSOXc45wZrpXFPBpFNLJpkovRKSuiVUObfKKWCOSCoqokrBgGgtQGle5lpxDUJxNkFvjn03sb3b-tSZdUjO17VtfLtNRtIcQHLSg3AEXWxTir4ymxjWNu4NEHO43Pzzt955NTTflmu__GsMj-qB1wNgk7N1FW3jQjpxqt8YaE-pI7ULtd__f66Zfpu9vQL-Z2t8VEPq_M-TauOtEZJJbr5eFyYvFqr48DE3n9gDj16Raw</recordid><startdate>200011</startdate><enddate>200011</enddate><creator>Lloyd, Barry A.</creator><creator>Arif, Atta M.</creator><creator>Allred, Evan L.</creator><general>Munksgaard International Publishers</general><general>Blackwell</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>200011</creationdate><title>A norbornenyl derivative with through-space ketone π-interaction</title><author>Lloyd, Barry A. ; Arif, Atta M. ; Allred, Evan L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4550-939492637c8d3736be8672cd1f45a8c813c0726f08b63109961895b4985916853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lloyd, Barry A.</creatorcontrib><creatorcontrib>Arif, Atta M.</creatorcontrib><creatorcontrib>Allred, Evan L.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lloyd, Barry A.</au><au>Arif, Atta M.</au><au>Allred, Evan L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A norbornenyl derivative with through-space ketone π-interaction</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Cryst. C</addtitle><date>2000-11</date><risdate>2000</risdate><volume>56</volume><issue>11</issue><spage>1377</spage><epage>1379</epage><pages>1377-1379</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><coden>ACSCEE</coden><abstract>The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­dodeca‐9‐en‐anti‐11‐yl p‐bromo­benzoate, C19H17BrO3, con­sists of norbornene with an anti‐p‐bromo­benzoate substituent at the methano bridge and an exo‐fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially pyramidalized. Through‐space ketone π‐inter­action is probably responsible for the low solvolysis rate of the anti‐11‐chloride derivative.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>Munksgaard International Publishers</pub><pmid>11077305</pmid><doi>10.1107/S0108270100011185</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0108-2701
ispartof Acta crystallographica. Section C, Crystal structure communications, 2000-11, Vol.56 (11), p.1377-1379
issn 0108-2701
1600-5759
language eng
recordid cdi_proquest_miscellaneous_72411750
source Crystallography Journals Online; Wiley Online Library Journals Frontfile Complete
subjects Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Organic compounds
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
title A norbornenyl derivative with through-space ketone π-interaction
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T11%3A01%3A00IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20norbornenyl%20derivative%20with%20through-space%20ketone%20%CF%80-interaction&rft.jtitle=Acta%20crystallographica.%20Section%20C,%20Crystal%20structure%20communications&rft.au=Lloyd,%20Barry%20A.&rft.date=2000-11&rft.volume=56&rft.issue=11&rft.spage=1377&rft.epage=1379&rft.pages=1377-1379&rft.issn=0108-2701&rft.eissn=1600-5759&rft.coden=ACSCEE&rft_id=info:doi/10.1107/S0108270100011185&rft_dat=%3Cproquest_cross%3E72411750%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=72411750&rft_id=info:pmid/11077305&rfr_iscdi=true