Synthesis of Diastereomeric Bicyclo[3.3.1]nonane Dibenzoyl Esters and Study of Their Chiroptical Properties
ABSTRACT A synthesis of diastereomeric bicyclic dibenzoyl esters derived from enantiomerically pure (1S,5S)‐bicyclo[3.3.1]nonane‐2,6‐dione was accomplished. Molecules containing two benzoyl chromophores with different configuration in the bicyclic framework were obtained. Chiroptical properties of t...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2012-10, Vol.24 (10), p.810-816 |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Bagdžiūnas, G. Butkus, E. Stončius, S. |
| description | ABSTRACT
A synthesis of diastereomeric bicyclic dibenzoyl esters derived from enantiomerically pure (1S,5S)‐bicyclo[3.3.1]nonane‐2,6‐dione was accomplished. Molecules containing two benzoyl chromophores with different configuration in the bicyclic framework were obtained. Chiroptical properties of the synthesized enantiomerically pure molecules were studied. Diastereomeric esters exhibited exciton couplets in the circular dichroism (CD) spectra because of transannular interaction between non‐conjugated benzoate chromophores. The conformational effects and solvent impact on the exciton coupling were examined by CD spectroscopy. Theoretical computation of the CD spectra of diastereomers correctly reproduced the sign of the exciton couplets in the studied molecules, however, no major solvent dielectric constant influence and conformational effects per se on the exciton coupling was observed. Chirality 24:810–816, 2012. © 2012 Wiley Periodicals, Inc. |
| doi_str_mv | 10.1002/chir.22075 |
| format | Article |
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A synthesis of diastereomeric bicyclic dibenzoyl esters derived from enantiomerically pure (1S,5S)‐bicyclo[3.3.1]nonane‐2,6‐dione was accomplished. Molecules containing two benzoyl chromophores with different configuration in the bicyclic framework were obtained. Chiroptical properties of the synthesized enantiomerically pure molecules were studied. Diastereomeric esters exhibited exciton couplets in the circular dichroism (CD) spectra because of transannular interaction between non‐conjugated benzoate chromophores. The conformational effects and solvent impact on the exciton coupling were examined by CD spectroscopy. Theoretical computation of the CD spectra of diastereomers correctly reproduced the sign of the exciton couplets in the studied molecules, however, no major solvent dielectric constant influence and conformational effects per se on the exciton coupling was observed. Chirality 24:810–816, 2012. © 2012 Wiley Periodicals, Inc.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.22075</identifier><identifier>PMID: 22760675</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>absolute configuration ; CD spectroscopy ; DFT calculations ; enantiospecific synthesis ; exciton coupling</subject><ispartof>Chirality (New York, N.Y.), 2012-10, Vol.24 (10), p.810-816</ispartof><rights>Copyright © 2012 Wiley Periodicals, Inc</rights><rights>Copyright © 2012 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3675-37faa7b8a368ba8870d1ffdda9a4e6ee5973bee09c6cadc6954667728fed4d323</citedby><cites>FETCH-LOGICAL-c3675-37faa7b8a368ba8870d1ffdda9a4e6ee5973bee09c6cadc6954667728fed4d323</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.22075$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.22075$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22760675$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bagdžiūnas, G.</creatorcontrib><creatorcontrib>Butkus, E.</creatorcontrib><creatorcontrib>Stončius, S.</creatorcontrib><title>Synthesis of Diastereomeric Bicyclo[3.3.1]nonane Dibenzoyl Esters and Study of Their Chiroptical Properties</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>ABSTRACT
A synthesis of diastereomeric bicyclic dibenzoyl esters derived from enantiomerically pure (1S,5S)‐bicyclo[3.3.1]nonane‐2,6‐dione was accomplished. Molecules containing two benzoyl chromophores with different configuration in the bicyclic framework were obtained. Chiroptical properties of the synthesized enantiomerically pure molecules were studied. Diastereomeric esters exhibited exciton couplets in the circular dichroism (CD) spectra because of transannular interaction between non‐conjugated benzoate chromophores. The conformational effects and solvent impact on the exciton coupling were examined by CD spectroscopy. Theoretical computation of the CD spectra of diastereomers correctly reproduced the sign of the exciton couplets in the studied molecules, however, no major solvent dielectric constant influence and conformational effects per se on the exciton coupling was observed. Chirality 24:810–816, 2012. © 2012 Wiley Periodicals, Inc.</description><subject>absolute configuration</subject><subject>CD spectroscopy</subject><subject>DFT calculations</subject><subject>enantiospecific synthesis</subject><subject>exciton coupling</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kM1O3DAURq2qqAy0mz4AyrKqlKl_EjtelhQGJAQIKFStkOXYNxqXTDzYGUF4-noYYNmVvTj36NNB6DPBU4Ix_WbmLkwpxaJ8hyakpDjnjP96jya4kjLHuKDbaCfGvxhjyVnxAW1TKjjmopygu8uxH-YQXcx8m_1wOg4QwC8gOJPtOzOazv9hUzYlt73vdQ-JaaB_8mOXHazZmOneZpfDyo5rw9UcXMjqtMgvB2d0l52nH4TBQfyItlrdRfj08u6in4cHV_VRfnI2O66_n-SGpU05E63Woqk041Wjq0pgS9rWWi11ARyglII1AFgabrQ1XJYF50LQqgVbWEbZLvqy8S6Dv19BHNTCRQNdl-b7VVQEV6RgRDKW0K8b1AQfY4BWLYNb6DAmSK3jqnVc9Rw3wXsv3lWzAPuGvtZMANkAD66D8T8qVR8dX7xK882NSzUf3250uFNcsITenM5UPbueyd_XF2qf_QOb6JVo</recordid><startdate>201210</startdate><enddate>201210</enddate><creator>Bagdžiūnas, G.</creator><creator>Butkus, E.</creator><creator>Stončius, S.</creator><general>Blackwell Publishing Ltd</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>201210</creationdate><title>Synthesis of Diastereomeric Bicyclo[3.3.1]nonane Dibenzoyl Esters and Study of Their Chiroptical Properties</title><author>Bagdžiūnas, G. ; Butkus, E. ; Stončius, S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3675-37faa7b8a368ba8870d1ffdda9a4e6ee5973bee09c6cadc6954667728fed4d323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>absolute configuration</topic><topic>CD spectroscopy</topic><topic>DFT calculations</topic><topic>enantiospecific synthesis</topic><topic>exciton coupling</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bagdžiūnas, G.</creatorcontrib><creatorcontrib>Butkus, E.</creatorcontrib><creatorcontrib>Stončius, S.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bagdžiūnas, G.</au><au>Butkus, E.</au><au>Stončius, S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Diastereomeric Bicyclo[3.3.1]nonane Dibenzoyl Esters and Study of Their Chiroptical Properties</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2012-10</date><risdate>2012</risdate><volume>24</volume><issue>10</issue><spage>810</spage><epage>816</epage><pages>810-816</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>ABSTRACT
A synthesis of diastereomeric bicyclic dibenzoyl esters derived from enantiomerically pure (1S,5S)‐bicyclo[3.3.1]nonane‐2,6‐dione was accomplished. Molecules containing two benzoyl chromophores with different configuration in the bicyclic framework were obtained. Chiroptical properties of the synthesized enantiomerically pure molecules were studied. Diastereomeric esters exhibited exciton couplets in the circular dichroism (CD) spectra because of transannular interaction between non‐conjugated benzoate chromophores. The conformational effects and solvent impact on the exciton coupling were examined by CD spectroscopy. Theoretical computation of the CD spectra of diastereomers correctly reproduced the sign of the exciton couplets in the studied molecules, however, no major solvent dielectric constant influence and conformational effects per se on the exciton coupling was observed. Chirality 24:810–816, 2012. © 2012 Wiley Periodicals, Inc.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>22760675</pmid><doi>10.1002/chir.22075</doi><tpages>7</tpages></addata></record> |
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| subjects | absolute configuration CD spectroscopy DFT calculations enantiospecific synthesis exciton coupling |
| title | Synthesis of Diastereomeric Bicyclo[3.3.1]nonane Dibenzoyl Esters and Study of Their Chiroptical Properties |
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