Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule
The hitherto elusive oxaziridine molecule (cyclo-H 2 CONH) - an optically active, high energy isomer of nitrosomethane (CH 3 NO) - is prepared in processed methane-nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes via additi...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-12, Vol.56 (1), p.15643-15646 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 15646 |
|---|---|
| container_issue | 1 |
| container_start_page | 15643 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 56 |
| creator | Singh, Santosh K La Jeunesse, Jesse Zhu, Cheng Kleimeier, N. Fabian Chen, Kuo-Hsin Sun, Bing-Jian Chang, Agnes H. H Kaiser, Ralf I |
| description | The hitherto elusive oxaziridine molecule (cyclo-H
2
CONH) - an optically active, high energy isomer of nitrosomethane (CH
3
NO) - is prepared in processed methane-nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes
via
addition of carbene (CH
2
) to the nitrogen-oxygen double bond of nitrosyl hydride (HNO). Our findings provide a fundamental framework to explore the preparation and stability of racemic oxaziridines exploited in chiral substrate-controlled diastereoselective preparation such as Sharpless asymmetric epoxidation, thus advancing our fundamental understanding of the preparation and chemical bonding of strained rings in small organic molecules.
First detection of the chiral oxaziridine (cyclo-H
2
CONH) molecule. |
| doi_str_mv | 10.1039/d0cc06760a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D0CC06760A</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2472769534</sourcerecordid><originalsourceid>FETCH-LOGICAL-c337t-2325497a44dd4d94ae03ffae14c4c340c5944fba29b35e1ae82bc66a30b8cd2c3</originalsourceid><addsrcrecordid>eNpd0ctLJDEQB-CwKKuOe_GuBLyo0Gs6qX4dh_YxwrBeXPDWm66uxkimM3a6xfGvN7PjA8ylAvmqKH5h7CAWv2OhivNGIIo0S4X-wXZjlUKUQH6_tb4nRZQpSHbYnvePIpw4yX-yHaVkDrJId9m_a-358kF74qahbjCtQT0Y13HX8uGBONnRm2fi7kW_mt40piN-giu0LpqVt39mpzziOujlEBqtXXGNw9ovnCUcLe2z7VZbT7_e64T9vbq8K2fR_Pb6ppzOI1QqGyKpZAJFpgGaBpoCNAnVtppiQEAFApMCoK21LGqVUKwplzWmqVaizrGRqCbsZDN32bunkfxQLYxHslZ35EZfSUizHESWx4Eef6OPbuy7sF1QmczSIlEQ1NlGYe-876mtlr1Z6H5VxaJa515diLL8n_s04KP3kWO9oOaTfgQdwOEG9B4_X78-Tr0Bbu6GdA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2472769534</pqid></control><display><type>article</type><title>Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Singh, Santosh K ; La Jeunesse, Jesse ; Zhu, Cheng ; Kleimeier, N. Fabian ; Chen, Kuo-Hsin ; Sun, Bing-Jian ; Chang, Agnes H. H ; Kaiser, Ralf I</creator><creatorcontrib>Singh, Santosh K ; La Jeunesse, Jesse ; Zhu, Cheng ; Kleimeier, N. Fabian ; Chen, Kuo-Hsin ; Sun, Bing-Jian ; Chang, Agnes H. H ; Kaiser, Ralf I</creatorcontrib><description>The hitherto elusive oxaziridine molecule (cyclo-H
2
CONH) - an optically active, high energy isomer of nitrosomethane (CH
3
NO) - is prepared in processed methane-nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes
via
addition of carbene (CH
2
) to the nitrogen-oxygen double bond of nitrosyl hydride (HNO). Our findings provide a fundamental framework to explore the preparation and stability of racemic oxaziridines exploited in chiral substrate-controlled diastereoselective preparation such as Sharpless asymmetric epoxidation, thus advancing our fundamental understanding of the preparation and chemical bonding of strained rings in small organic molecules.
First detection of the chiral oxaziridine (cyclo-H
2
CONH) molecule.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc06760a</identifier><identifier>PMID: 33284296</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemical bonds ; Control stability ; Electronic structure ; Epoxidation ; Nitric oxide ; Optical activity ; Organic chemistry ; Stereoselectivity ; Sublimation ; Substrates ; Vapor phases</subject><ispartof>Chemical communications (Cambridge, England), 2020-12, Vol.56 (1), p.15643-15646</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-2325497a44dd4d94ae03ffae14c4c340c5944fba29b35e1ae82bc66a30b8cd2c3</citedby><cites>FETCH-LOGICAL-c337t-2325497a44dd4d94ae03ffae14c4c340c5944fba29b35e1ae82bc66a30b8cd2c3</cites><orcidid>0000-0002-7256-672X ; 0000-0002-7233-7206</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33284296$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Singh, Santosh K</creatorcontrib><creatorcontrib>La Jeunesse, Jesse</creatorcontrib><creatorcontrib>Zhu, Cheng</creatorcontrib><creatorcontrib>Kleimeier, N. Fabian</creatorcontrib><creatorcontrib>Chen, Kuo-Hsin</creatorcontrib><creatorcontrib>Sun, Bing-Jian</creatorcontrib><creatorcontrib>Chang, Agnes H. H</creatorcontrib><creatorcontrib>Kaiser, Ralf I</creatorcontrib><title>Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The hitherto elusive oxaziridine molecule (cyclo-H
2
CONH) - an optically active, high energy isomer of nitrosomethane (CH
3
NO) - is prepared in processed methane-nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes
via
addition of carbene (CH
2
) to the nitrogen-oxygen double bond of nitrosyl hydride (HNO). Our findings provide a fundamental framework to explore the preparation and stability of racemic oxaziridines exploited in chiral substrate-controlled diastereoselective preparation such as Sharpless asymmetric epoxidation, thus advancing our fundamental understanding of the preparation and chemical bonding of strained rings in small organic molecules.
First detection of the chiral oxaziridine (cyclo-H
2
CONH) molecule.</description><subject>Chemical bonds</subject><subject>Control stability</subject><subject>Electronic structure</subject><subject>Epoxidation</subject><subject>Nitric oxide</subject><subject>Optical activity</subject><subject>Organic chemistry</subject><subject>Stereoselectivity</subject><subject>Sublimation</subject><subject>Substrates</subject><subject>Vapor phases</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpd0ctLJDEQB-CwKKuOe_GuBLyo0Gs6qX4dh_YxwrBeXPDWm66uxkimM3a6xfGvN7PjA8ylAvmqKH5h7CAWv2OhivNGIIo0S4X-wXZjlUKUQH6_tb4nRZQpSHbYnvePIpw4yX-yHaVkDrJId9m_a-358kF74qahbjCtQT0Y13HX8uGBONnRm2fi7kW_mt40piN-giu0LpqVt39mpzziOujlEBqtXXGNw9ovnCUcLe2z7VZbT7_e64T9vbq8K2fR_Pb6ppzOI1QqGyKpZAJFpgGaBpoCNAnVtppiQEAFApMCoK21LGqVUKwplzWmqVaizrGRqCbsZDN32bunkfxQLYxHslZ35EZfSUizHESWx4Eef6OPbuy7sF1QmczSIlEQ1NlGYe-876mtlr1Z6H5VxaJa515diLL8n_s04KP3kWO9oOaTfgQdwOEG9B4_X78-Tr0Bbu6GdA</recordid><startdate>20201221</startdate><enddate>20201221</enddate><creator>Singh, Santosh K</creator><creator>La Jeunesse, Jesse</creator><creator>Zhu, Cheng</creator><creator>Kleimeier, N. Fabian</creator><creator>Chen, Kuo-Hsin</creator><creator>Sun, Bing-Jian</creator><creator>Chang, Agnes H. H</creator><creator>Kaiser, Ralf I</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7256-672X</orcidid><orcidid>https://orcid.org/0000-0002-7233-7206</orcidid></search><sort><creationdate>20201221</creationdate><title>Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule</title><author>Singh, Santosh K ; La Jeunesse, Jesse ; Zhu, Cheng ; Kleimeier, N. Fabian ; Chen, Kuo-Hsin ; Sun, Bing-Jian ; Chang, Agnes H. H ; Kaiser, Ralf I</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-2325497a44dd4d94ae03ffae14c4c340c5944fba29b35e1ae82bc66a30b8cd2c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemical bonds</topic><topic>Control stability</topic><topic>Electronic structure</topic><topic>Epoxidation</topic><topic>Nitric oxide</topic><topic>Optical activity</topic><topic>Organic chemistry</topic><topic>Stereoselectivity</topic><topic>Sublimation</topic><topic>Substrates</topic><topic>Vapor phases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Singh, Santosh K</creatorcontrib><creatorcontrib>La Jeunesse, Jesse</creatorcontrib><creatorcontrib>Zhu, Cheng</creatorcontrib><creatorcontrib>Kleimeier, N. Fabian</creatorcontrib><creatorcontrib>Chen, Kuo-Hsin</creatorcontrib><creatorcontrib>Sun, Bing-Jian</creatorcontrib><creatorcontrib>Chang, Agnes H. H</creatorcontrib><creatorcontrib>Kaiser, Ralf I</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Singh, Santosh K</au><au>La Jeunesse, Jesse</au><au>Zhu, Cheng</au><au>Kleimeier, N. Fabian</au><au>Chen, Kuo-Hsin</au><au>Sun, Bing-Jian</au><au>Chang, Agnes H. H</au><au>Kaiser, Ralf I</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-12-21</date><risdate>2020</risdate><volume>56</volume><issue>1</issue><spage>15643</spage><epage>15646</epage><pages>15643-15646</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The hitherto elusive oxaziridine molecule (cyclo-H
2
CONH) - an optically active, high energy isomer of nitrosomethane (CH
3
NO) - is prepared in processed methane-nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes
via
addition of carbene (CH
2
) to the nitrogen-oxygen double bond of nitrosyl hydride (HNO). Our findings provide a fundamental framework to explore the preparation and stability of racemic oxaziridines exploited in chiral substrate-controlled diastereoselective preparation such as Sharpless asymmetric epoxidation, thus advancing our fundamental understanding of the preparation and chemical bonding of strained rings in small organic molecules.
First detection of the chiral oxaziridine (cyclo-H
2
CONH) molecule.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33284296</pmid><doi>10.1039/d0cc06760a</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-7256-672X</orcidid><orcidid>https://orcid.org/0000-0002-7233-7206</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-12, Vol.56 (1), p.15643-15646 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D0CC06760A |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical bonds Control stability Electronic structure Epoxidation Nitric oxide Optical activity Organic chemistry Stereoselectivity Sublimation Substrates Vapor phases |
| title | Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T20%3A37%3A19IST&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=Gas%20phase%20identification%20of%20the%20elusive%20oxaziridine%20(cyclo-HCONH)%20-%20an%20optically%20active%20molecule&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Singh,%20Santosh%20K&rft.date=2020-12-21&rft.volume=56&rft.issue=1&rft.spage=15643&rft.epage=15646&rft.pages=15643-15646&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d0cc06760a&rft_dat=%3Cproquest_cross%3E2472769534%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=2472769534&rft_id=info:pmid/33284296&rfr_iscdi=true |