Crystal structure analysis of enantiomerically pure (+) and (−) β-hexabromocyclododecanes
The molecular structures of individual HBCD stereoisomers are not elucidated yet. Recently, we isolated 8 of the 16 possible stereoisomers from a technical HBCD mixture and tentatively assigned their relative configurations. Herein we report on the isolation of enantiomerically pure (+) and (−) β-HB...
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| Veröffentlicht in: | Chemosphere (Oxford) 2007, Vol.66 (8), p.1590-1594 |
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| creator | Heeb, Norbert V. Bernd Schweizer, W. Mattrel, Peter Haag, Regula Kohler, Martin |
| description | The molecular structures of individual HBCD stereoisomers are not elucidated yet. Recently, we isolated 8 of the 16 possible stereoisomers from a technical HBCD mixture and tentatively assigned their relative configurations. Herein we report on the isolation of enantiomerically pure (+) and (−) β-HBCDs, both obtained from preparative chiral-phase liquid chromatography, and we present their absolute configurations determined from X-ray diffraction analysis. The absolute configuration of (+) β-HBCD was found to be (1S,
2S,
5S,
6R,
9S,
10R), while the one of (−) β-HBCD was assigned to (1R,
2R,
5R,
6S,
9R,
10S). The given structural information allows, for the first time, the unambiguous identification of these two important HBCD stereoisomers, which are typically found in technical products at proportions of about 3–5% for each enantiomer. |
| doi_str_mv | 10.1016/j.chemosphere.2006.09.051 |
| format | Article |
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2S,
5S,
6R,
9S,
10R), while the one of (−) β-HBCD was assigned to (1R,
2R,
5R,
6S,
9R,
10S). The given structural information allows, for the first time, the unambiguous identification of these two important HBCD stereoisomers, which are typically found in technical products at proportions of about 3–5% for each enantiomer.</description><identifier>ISSN: 0045-6535</identifier><identifier>EISSN: 1879-1298</identifier><identifier>DOI: 10.1016/j.chemosphere.2006.09.051</identifier><identifier>PMID: 17113625</identifier><identifier>CODEN: CMSHAF</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Absolute configuration ; Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; Applied sciences ; Chromatography, Liquid ; Condensed matter: structure, mechanical and thermal properties ; Crystal structure ; Crystallography, X-Ray - methods ; Earth sciences ; Earth, ocean, space ; Engineering and environment geology. Geothermics ; Exact sciences and technology ; Global environmental pollution ; HBCDs ; Hydrocarbons, Brominated - chemistry ; Hydrocarbons, Brominated - isolation & purification ; Mass Spectrometry ; Molecular Structure ; Organic compounds ; Physics ; Pollution ; Pollution, environment geology ; Resolution of enantiomers ; Stereoisomerism ; Stereoisomers ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Chemosphere (Oxford), 2007, Vol.66 (8), p.1590-1594</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-ea0b61f2d3d8eca10693835188fdcd9c08aa6eb7655875eaa684aa9dee3a352e3</citedby><cites>FETCH-LOGICAL-c405t-ea0b61f2d3d8eca10693835188fdcd9c08aa6eb7655875eaa684aa9dee3a352e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chemosphere.2006.09.051$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,4022,27921,27922,27923,45993</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18460890$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17113625$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Heeb, Norbert V.</creatorcontrib><creatorcontrib>Bernd Schweizer, W.</creatorcontrib><creatorcontrib>Mattrel, Peter</creatorcontrib><creatorcontrib>Haag, Regula</creatorcontrib><creatorcontrib>Kohler, Martin</creatorcontrib><title>Crystal structure analysis of enantiomerically pure (+) and (−) β-hexabromocyclododecanes</title><title>Chemosphere (Oxford)</title><addtitle>Chemosphere</addtitle><description>The molecular structures of individual HBCD stereoisomers are not elucidated yet. Recently, we isolated 8 of the 16 possible stereoisomers from a technical HBCD mixture and tentatively assigned their relative configurations. Herein we report on the isolation of enantiomerically pure (+) and (−) β-HBCDs, both obtained from preparative chiral-phase liquid chromatography, and we present their absolute configurations determined from X-ray diffraction analysis. The absolute configuration of (+) β-HBCD was found to be (1S,
2S,
5S,
6R,
9S,
10R), while the one of (−) β-HBCD was assigned to (1R,
2R,
5R,
6S,
9R,
10S). The given structural information allows, for the first time, the unambiguous identification of these two important HBCD stereoisomers, which are typically found in technical products at proportions of about 3–5% for each enantiomer.</description><subject>Absolute configuration</subject><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>Applied sciences</subject><subject>Chromatography, Liquid</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Crystal structure</subject><subject>Crystallography, X-Ray - methods</subject><subject>Earth sciences</subject><subject>Earth, ocean, space</subject><subject>Engineering and environment geology. Geothermics</subject><subject>Exact sciences and technology</subject><subject>Global environmental pollution</subject><subject>HBCDs</subject><subject>Hydrocarbons, Brominated - chemistry</subject><subject>Hydrocarbons, Brominated - isolation & purification</subject><subject>Mass Spectrometry</subject><subject>Molecular Structure</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Pollution</subject><subject>Pollution, environment geology</subject><subject>Resolution of enantiomers</subject><subject>Stereoisomerism</subject><subject>Stereoisomers</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0045-6535</issn><issn>1879-1298</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkM9q3DAQh0VoabZpXyG4h5aEYndkrWTpWJb0DwRySW8FoZXGrBbb2kp2iN-g5z5KHyQP0SeJll1IjzkNA99v5sdHyDsKFQUqPm0ru8E-pN0GI1Y1gKhAVcDpCVlQ2aiS1kq-IAuAJS8FZ_yUvE5pC5DDXL0ip7ShlImaL8jPVZzTaLoijXGy4xSxMIPp5uRTEdoCBzOMPvQYvTVdNxe7PXHx8TJTrrj49_vPZfHwt9zgvVnH0Ac72y644NCaAdMb8rI1XcK3x3lGfny5ul19K69vvn5ffb4u7RL4WKKBtaBt7ZiTOUhBKCYZp1K2zjplQRojcN0IzmXDMS9yaYxyiMwwXiM7Ix8Od3cx_Jowjbr3yWLX5RJhSlpIJkQDNIPqANoYUorY6l30vYmzpqD3avVW_6dW79VqUDqrzdnz45Np3aN7Sh5dZuD9ETApy2qjGaxPT5xcCpAKMrc6cJiV3HmMOlmPg0XnI9pRu-CfUecRCo-gcg</recordid><startdate>2007</startdate><enddate>2007</enddate><creator>Heeb, Norbert V.</creator><creator>Bernd Schweizer, W.</creator><creator>Mattrel, Peter</creator><creator>Haag, Regula</creator><creator>Kohler, Martin</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><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>2007</creationdate><title>Crystal structure analysis of enantiomerically pure (+) and (−) β-hexabromocyclododecanes</title><author>Heeb, Norbert V. ; Bernd Schweizer, W. ; Mattrel, Peter ; Haag, Regula ; Kohler, Martin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-ea0b61f2d3d8eca10693835188fdcd9c08aa6eb7655875eaa684aa9dee3a352e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Absolute configuration</topic><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>Applied sciences</topic><topic>Chromatography, Liquid</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Crystal structure</topic><topic>Crystallography, X-Ray - methods</topic><topic>Earth sciences</topic><topic>Earth, ocean, space</topic><topic>Engineering and environment geology. Geothermics</topic><topic>Exact sciences and technology</topic><topic>Global environmental pollution</topic><topic>HBCDs</topic><topic>Hydrocarbons, Brominated - chemistry</topic><topic>Hydrocarbons, Brominated - isolation & purification</topic><topic>Mass Spectrometry</topic><topic>Molecular Structure</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Pollution</topic><topic>Pollution, environment geology</topic><topic>Resolution of enantiomers</topic><topic>Stereoisomerism</topic><topic>Stereoisomers</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>Heeb, Norbert V.</creatorcontrib><creatorcontrib>Bernd Schweizer, W.</creatorcontrib><creatorcontrib>Mattrel, Peter</creatorcontrib><creatorcontrib>Haag, Regula</creatorcontrib><creatorcontrib>Kohler, Martin</creatorcontrib><collection>Pascal-Francis</collection><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>Chemosphere (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Heeb, Norbert V.</au><au>Bernd Schweizer, W.</au><au>Mattrel, Peter</au><au>Haag, Regula</au><au>Kohler, Martin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Crystal structure analysis of enantiomerically pure (+) and (−) β-hexabromocyclododecanes</atitle><jtitle>Chemosphere (Oxford)</jtitle><addtitle>Chemosphere</addtitle><date>2007</date><risdate>2007</risdate><volume>66</volume><issue>8</issue><spage>1590</spage><epage>1594</epage><pages>1590-1594</pages><issn>0045-6535</issn><eissn>1879-1298</eissn><coden>CMSHAF</coden><abstract>The molecular structures of individual HBCD stereoisomers are not elucidated yet. Recently, we isolated 8 of the 16 possible stereoisomers from a technical HBCD mixture and tentatively assigned their relative configurations. Herein we report on the isolation of enantiomerically pure (+) and (−) β-HBCDs, both obtained from preparative chiral-phase liquid chromatography, and we present their absolute configurations determined from X-ray diffraction analysis. The absolute configuration of (+) β-HBCD was found to be (1S,
2S,
5S,
6R,
9S,
10R), while the one of (−) β-HBCD was assigned to (1R,
2R,
5R,
6S,
9R,
10S). The given structural information allows, for the first time, the unambiguous identification of these two important HBCD stereoisomers, which are typically found in technical products at proportions of about 3–5% for each enantiomer.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17113625</pmid><doi>10.1016/j.chemosphere.2006.09.051</doi><tpages>5</tpages></addata></record> |
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| subjects | Absolute configuration Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds Applied sciences Chromatography, Liquid Condensed matter: structure, mechanical and thermal properties Crystal structure Crystallography, X-Ray - methods Earth sciences Earth, ocean, space Engineering and environment geology. Geothermics Exact sciences and technology Global environmental pollution HBCDs Hydrocarbons, Brominated - chemistry Hydrocarbons, Brominated - isolation & purification Mass Spectrometry Molecular Structure Organic compounds Physics Pollution Pollution, environment geology Resolution of enantiomers Stereoisomerism Stereoisomers Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | Crystal structure analysis of enantiomerically pure (+) and (−) β-hexabromocyclododecanes |
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