Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory
Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C₃H₂) has been presumed to be too unstable to isolate in the laboratory. However, by appending π-electron-donating amino groups to the triangular skeleton, we prepared a cyc...
Gespeichert in:
| Veröffentlicht in: | Science (American Association for the Advancement of Science) 2006-05, Vol.312 (5774), p.722-724 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 724 |
|---|---|
| container_issue | 5774 |
| container_start_page | 722 |
| container_title | Science (American Association for the Advancement of Science) |
| container_volume | 312 |
| creator | Lavallo, Vincent Canac, Yves Donnadieu, Bruno Schoeller, Wolfgang W Bertrand, Guy |
| description | Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C₃H₂) has been presumed to be too unstable to isolate in the laboratory. However, by appending π-electron-donating amino groups to the triangular skeleton, we prepared a cyclopropenylidene derivative that is stable at room temperature. In contrast to previously isolated carbenes, this compound does not require a heteroatom adjacent to the electron-deficient carbon to confer stability. Despite the presence of amino groups, the geometric parameters of the cyclic skeleton, revealed by x-ray crystallography, are only slightly perturbed relative to those of the calculated structure of unsubstituted cyclopropenylidene. Stable cyclopropenylidene derivatives might thus serve as models for a better understanding of the formation of carbon-bearing molecules in the interstellar medium. |
| doi_str_mv | 10.1126/science.1126675 |
| format | Article |
| fullrecord | <record><control><sourceid>jstor_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2427275</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><jstor_id>3846091</jstor_id><sourcerecordid>3846091</sourcerecordid><originalsourceid>FETCH-LOGICAL-c685t-83516d1523456a33911b8925a0dd6b0cb38cb6b68f700b544ce8c9b47c9a55af3</originalsourceid><addsrcrecordid>eNqFks1vEzEQxS0EoiFw5oJghQQSh9Cxvf7igFSllEaKxKFU4mZ5vd5mo42d2ptI-e_xNqsWeunJst9v3sgzD6G3GL5iTPhpsq3z1t1duGDP0ASDYjNFgD5HEwDKZxIEO0GvUloDZE3Rl-gEc45LLPAE_ZkfbBe2MWydP3Rt7bxL34qLGDbFwvcupt51nYnF1dZYV_ShML5YpNCZ3tXFuYvt3vTt3hWtL_qVK5amCtH0IR5eoxeN6ZJ7M55TdH3x4_f8crb89XMxP1vOLJesn0nKMK8xI7Rk3FCqMK6kIsxAXfMKbEWlrXjFZSMAKlaW1kmrqlJYZRgzDZ2i70ff7a7auNo630fT6W1sNyYedDCt_l_x7UrfhL0mJRFEsGzw5WiwelR2ebbUwxtQQRXnsMeZ_Tw2i-F251KvN22yw4S8C7ukuVC0LDP_FEhk3gXn7EkQq5JiQgbHj4_AddhFn0erCaYcC5F7T9HpEbIxpBRdc_8hDHrIiB4Do8fA5Ir3_47vgR8TkoFPI2CSNV0TjbdteuCEZABy4N4duXXK67_XqSw5qEH-cJQbE7S5idni-ooApoBBSAWM_gWz-tv7</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>213617779</pqid></control><display><type>article</type><title>Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory</title><source>American Association for the Advancement of Science</source><source>Jstor Complete Legacy</source><source>MEDLINE</source><creator>Lavallo, Vincent ; Canac, Yves ; Donnadieu, Bruno ; Schoeller, Wolfgang W ; Bertrand, Guy</creator><creatorcontrib>Lavallo, Vincent ; Canac, Yves ; Donnadieu, Bruno ; Schoeller, Wolfgang W ; Bertrand, Guy</creatorcontrib><description>Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C₃H₂) has been presumed to be too unstable to isolate in the laboratory. However, by appending π-electron-donating amino groups to the triangular skeleton, we prepared a cyclopropenylidene derivative that is stable at room temperature. In contrast to previously isolated carbenes, this compound does not require a heteroatom adjacent to the electron-deficient carbon to confer stability. Despite the presence of amino groups, the geometric parameters of the cyclic skeleton, revealed by x-ray crystallography, are only slightly perturbed relative to those of the calculated structure of unsubstituted cyclopropenylidene. Stable cyclopropenylidene derivatives might thus serve as models for a better understanding of the formation of carbon-bearing molecules in the interstellar medium.</description><identifier>ISSN: 0036-8075</identifier><identifier>EISSN: 1095-9203</identifier><identifier>DOI: 10.1126/science.1126675</identifier><identifier>PMID: 16614171</identifier><identifier>CODEN: SCIEAS</identifier><language>eng</language><publisher>Washington, DC: American Association for the Advancement of Science</publisher><subject>Astronomy ; Astrophysics ; Atomic, molecular, chemical, and grain processes ; Carbenes ; Carbon ; Chemical compounds ; Chemical Sciences ; Chemistry ; Coordination chemistry ; Crystallography ; Crystallography, X-Ray ; Cyclopropanes - chemistry ; Cyclopropanes - isolation & purification ; Earth, ocean, space ; Exact sciences and technology ; Extraterrestrial Environment ; Fundamental aspects of astrophysics ; Fundamental astronomy and astrophysics. Instrumentation, techniques, and astronomical observations ; Heterocyclic compounds ; Interstellar chemistry ; Interstellar medium ; Interstellar medium (ism) and nebulae in milky way ; Interstellar space ; Laboratories ; Magnetic Resonance Spectroscopy ; Molecular and chemical processes and interactions ; Molecular Structure ; Molecules ; Organic chemistry ; Preparations and properties ; Room temperature ; Salts ; Space laboratories ; Stellar systems. Galactic and extragalactic objects and systems. The universe ; Temperature ; Thermodynamics</subject><ispartof>Science (American Association for the Advancement of Science), 2006-05, Vol.312 (5774), p.722-724</ispartof><rights>Copyright 2006 American Association for the Advancement of Science</rights><rights>2006 INIST-CNRS</rights><rights>Copyright American Association for the Advancement of Science May 5, 2006</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c685t-83516d1523456a33911b8925a0dd6b0cb38cb6b68f700b544ce8c9b47c9a55af3</citedby><cites>FETCH-LOGICAL-c685t-83516d1523456a33911b8925a0dd6b0cb38cb6b68f700b544ce8c9b47c9a55af3</cites><orcidid>0000-0002-3747-554X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/3846091$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/3846091$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,776,780,799,881,2871,2872,27901,27902,57992,58225</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17850081$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16614171$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03739660$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Lavallo, Vincent</creatorcontrib><creatorcontrib>Canac, Yves</creatorcontrib><creatorcontrib>Donnadieu, Bruno</creatorcontrib><creatorcontrib>Schoeller, Wolfgang W</creatorcontrib><creatorcontrib>Bertrand, Guy</creatorcontrib><title>Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory</title><title>Science (American Association for the Advancement of Science)</title><addtitle>Science</addtitle><description>Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C₃H₂) has been presumed to be too unstable to isolate in the laboratory. However, by appending π-electron-donating amino groups to the triangular skeleton, we prepared a cyclopropenylidene derivative that is stable at room temperature. In contrast to previously isolated carbenes, this compound does not require a heteroatom adjacent to the electron-deficient carbon to confer stability. Despite the presence of amino groups, the geometric parameters of the cyclic skeleton, revealed by x-ray crystallography, are only slightly perturbed relative to those of the calculated structure of unsubstituted cyclopropenylidene. Stable cyclopropenylidene derivatives might thus serve as models for a better understanding of the formation of carbon-bearing molecules in the interstellar medium.</description><subject>Astronomy</subject><subject>Astrophysics</subject><subject>Atomic, molecular, chemical, and grain processes</subject><subject>Carbenes</subject><subject>Carbon</subject><subject>Chemical compounds</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Coordination chemistry</subject><subject>Crystallography</subject><subject>Crystallography, X-Ray</subject><subject>Cyclopropanes - chemistry</subject><subject>Cyclopropanes - isolation & purification</subject><subject>Earth, ocean, space</subject><subject>Exact sciences and technology</subject><subject>Extraterrestrial Environment</subject><subject>Fundamental aspects of astrophysics</subject><subject>Fundamental astronomy and astrophysics. Instrumentation, techniques, and astronomical observations</subject><subject>Heterocyclic compounds</subject><subject>Interstellar chemistry</subject><subject>Interstellar medium</subject><subject>Interstellar medium (ism) and nebulae in milky way</subject><subject>Interstellar space</subject><subject>Laboratories</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular and chemical processes and interactions</subject><subject>Molecular Structure</subject><subject>Molecules</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Room temperature</subject><subject>Salts</subject><subject>Space laboratories</subject><subject>Stellar systems. Galactic and extragalactic objects and systems. The universe</subject><subject>Temperature</subject><subject>Thermodynamics</subject><issn>0036-8075</issn><issn>1095-9203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFks1vEzEQxS0EoiFw5oJghQQSh9Cxvf7igFSllEaKxKFU4mZ5vd5mo42d2ptI-e_xNqsWeunJst9v3sgzD6G3GL5iTPhpsq3z1t1duGDP0ASDYjNFgD5HEwDKZxIEO0GvUloDZE3Rl-gEc45LLPAE_ZkfbBe2MWydP3Rt7bxL34qLGDbFwvcupt51nYnF1dZYV_ShML5YpNCZ3tXFuYvt3vTt3hWtL_qVK5amCtH0IR5eoxeN6ZJ7M55TdH3x4_f8crb89XMxP1vOLJesn0nKMK8xI7Rk3FCqMK6kIsxAXfMKbEWlrXjFZSMAKlaW1kmrqlJYZRgzDZ2i70ff7a7auNo630fT6W1sNyYedDCt_l_x7UrfhL0mJRFEsGzw5WiwelR2ebbUwxtQQRXnsMeZ_Tw2i-F251KvN22yw4S8C7ukuVC0LDP_FEhk3gXn7EkQq5JiQgbHj4_AddhFn0erCaYcC5F7T9HpEbIxpBRdc_8hDHrIiB4Do8fA5Ir3_47vgR8TkoFPI2CSNV0TjbdteuCEZABy4N4duXXK67_XqSw5qEH-cJQbE7S5idni-ooApoBBSAWM_gWz-tv7</recordid><startdate>20060505</startdate><enddate>20060505</enddate><creator>Lavallo, Vincent</creator><creator>Canac, Yves</creator><creator>Donnadieu, Bruno</creator><creator>Schoeller, Wolfgang W</creator><creator>Bertrand, Guy</creator><general>American Association for the Advancement of Science</general><general>The American Association for the Advancement of Science</general><general>American Association for the Advancement of Science (AAAS)</general><scope>FBQ</scope><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>7QF</scope><scope>7QG</scope><scope>7QL</scope><scope>7QP</scope><scope>7QQ</scope><scope>7QR</scope><scope>7SC</scope><scope>7SE</scope><scope>7SN</scope><scope>7SP</scope><scope>7SR</scope><scope>7SS</scope><scope>7T7</scope><scope>7TA</scope><scope>7TB</scope><scope>7TK</scope><scope>7TM</scope><scope>7U5</scope><scope>7U9</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H94</scope><scope>JG9</scope><scope>JQ2</scope><scope>K9.</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>M7N</scope><scope>P64</scope><scope>RC3</scope><scope>7TG</scope><scope>KL.</scope><scope>7X8</scope><scope>1XC</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3747-554X</orcidid></search><sort><creationdate>20060505</creationdate><title>Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory</title><author>Lavallo, Vincent ; Canac, Yves ; Donnadieu, Bruno ; Schoeller, Wolfgang W ; Bertrand, Guy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c685t-83516d1523456a33911b8925a0dd6b0cb38cb6b68f700b544ce8c9b47c9a55af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Astronomy</topic><topic>Astrophysics</topic><topic>Atomic, molecular, chemical, and grain processes</topic><topic>Carbenes</topic><topic>Carbon</topic><topic>Chemical compounds</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Coordination chemistry</topic><topic>Crystallography</topic><topic>Crystallography, X-Ray</topic><topic>Cyclopropanes - chemistry</topic><topic>Cyclopropanes - isolation & purification</topic><topic>Earth, ocean, space</topic><topic>Exact sciences and technology</topic><topic>Extraterrestrial Environment</topic><topic>Fundamental aspects of astrophysics</topic><topic>Fundamental astronomy and astrophysics. Instrumentation, techniques, and astronomical observations</topic><topic>Heterocyclic compounds</topic><topic>Interstellar chemistry</topic><topic>Interstellar medium</topic><topic>Interstellar medium (ism) and nebulae in milky way</topic><topic>Interstellar space</topic><topic>Laboratories</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular and chemical processes and interactions</topic><topic>Molecular Structure</topic><topic>Molecules</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Room temperature</topic><topic>Salts</topic><topic>Space laboratories</topic><topic>Stellar systems. Galactic and extragalactic objects and systems. The universe</topic><topic>Temperature</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lavallo, Vincent</creatorcontrib><creatorcontrib>Canac, Yves</creatorcontrib><creatorcontrib>Donnadieu, Bruno</creatorcontrib><creatorcontrib>Schoeller, Wolfgang W</creatorcontrib><creatorcontrib>Bertrand, Guy</creatorcontrib><collection>AGRIS</collection><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>Aluminium Industry Abstracts</collection><collection>Animal Behavior Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Ecology Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>Meteorological & Geoastrophysical Abstracts</collection><collection>Meteorological & Geoastrophysical Abstracts - Academic</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Science (American Association for the Advancement of Science)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lavallo, Vincent</au><au>Canac, Yves</au><au>Donnadieu, Bruno</au><au>Schoeller, Wolfgang W</au><au>Bertrand, Guy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory</atitle><jtitle>Science (American Association for the Advancement of Science)</jtitle><addtitle>Science</addtitle><date>2006-05-05</date><risdate>2006</risdate><volume>312</volume><issue>5774</issue><spage>722</spage><epage>724</epage><pages>722-724</pages><issn>0036-8075</issn><eissn>1095-9203</eissn><coden>SCIEAS</coden><abstract>Like many of the molecular species that have been detected in the interstellar medium, the singlet carbene cyclopropenylidene (C₃H₂) has been presumed to be too unstable to isolate in the laboratory. However, by appending π-electron-donating amino groups to the triangular skeleton, we prepared a cyclopropenylidene derivative that is stable at room temperature. In contrast to previously isolated carbenes, this compound does not require a heteroatom adjacent to the electron-deficient carbon to confer stability. Despite the presence of amino groups, the geometric parameters of the cyclic skeleton, revealed by x-ray crystallography, are only slightly perturbed relative to those of the calculated structure of unsubstituted cyclopropenylidene. Stable cyclopropenylidene derivatives might thus serve as models for a better understanding of the formation of carbon-bearing molecules in the interstellar medium.</abstract><cop>Washington, DC</cop><pub>American Association for the Advancement of Science</pub><pmid>16614171</pmid><doi>10.1126/science.1126675</doi><tpages>3</tpages><orcidid>https://orcid.org/0000-0002-3747-554X</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0036-8075 |
| ispartof | Science (American Association for the Advancement of Science), 2006-05, Vol.312 (5774), p.722-724 |
| issn | 0036-8075 1095-9203 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2427275 |
| source | American Association for the Advancement of Science; Jstor Complete Legacy; MEDLINE |
| subjects | Astronomy Astrophysics Atomic, molecular, chemical, and grain processes Carbenes Carbon Chemical compounds Chemical Sciences Chemistry Coordination chemistry Crystallography Crystallography, X-Ray Cyclopropanes - chemistry Cyclopropanes - isolation & purification Earth, ocean, space Exact sciences and technology Extraterrestrial Environment Fundamental aspects of astrophysics Fundamental astronomy and astrophysics. Instrumentation, techniques, and astronomical observations Heterocyclic compounds Interstellar chemistry Interstellar medium Interstellar medium (ism) and nebulae in milky way Interstellar space Laboratories Magnetic Resonance Spectroscopy Molecular and chemical processes and interactions Molecular Structure Molecules Organic chemistry Preparations and properties Room temperature Salts Space laboratories Stellar systems. Galactic and extragalactic objects and systems. The universe Temperature Thermodynamics |
| title | Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T07%3A14%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-jstor_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Cyclopropenylidenes:%20From%20Interstellar%20Space%20to%20an%20Isolated%20Derivative%20in%20the%20Laboratory&rft.jtitle=Science%20(American%20Association%20for%20the%20Advancement%20of%20Science)&rft.au=Lavallo,%20Vincent&rft.date=2006-05-05&rft.volume=312&rft.issue=5774&rft.spage=722&rft.epage=724&rft.pages=722-724&rft.issn=0036-8075&rft.eissn=1095-9203&rft.coden=SCIEAS&rft_id=info:doi/10.1126/science.1126675&rft_dat=%3Cjstor_pubme%3E3846091%3C/jstor_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=213617779&rft_id=info:pmid/16614171&rft_jstor_id=3846091&rfr_iscdi=true |