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Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold
In accord with its gas phase acidity, toluene is activated by atomic oxygen adsorbed on Au(111) at the methyl C–H bonds. Titration of this species from the surface with HCOOD yields C 6 H 5 CHD 2 , indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low sur...
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| Published in: | Catalysis letters 2018-07, Vol.148 (7), p.1985-1989 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c481t-fa7182710803a3767074853adbb6e86950b27f6c7434cce66e37081c329cb1fe3 |
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| cites | cdi_FETCH-LOGICAL-c481t-fa7182710803a3767074853adbb6e86950b27f6c7434cce66e37081c329cb1fe3 |
| container_end_page | 1989 |
| container_issue | 7 |
| container_start_page | 1985 |
| container_title | Catalysis letters |
| container_volume | 148 |
| creator | Rodríguez-Reyes, Juan Carlos F. Friend, Cynthia M. Madix, Robert J. |
| description | In accord with its gas phase acidity, toluene is activated by atomic oxygen adsorbed on Au(111) at the methyl C–H bonds. Titration of this species from the surface with HCOOD yields C
6
H
5
CHD
2
, indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low surface coverages of atomic oxygen the thusly-activated species yields only CO, CO
2
and water as gas phase products when heated above room temperature, indicating the facile formation of an adsorbed benzoate, not simple oxygen insertion into the carbene to form benzyl benzyloxy. At higher O pre-coverages benzoic acid forms between 400 and 500 K.
Graphical Abstract |
| doi_str_mv | 10.1007/s10562-018-2407-3 |
| format | article |
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6
H
5
CHD
2
, indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low surface coverages of atomic oxygen the thusly-activated species yields only CO, CO
2
and water as gas phase products when heated above room temperature, indicating the facile formation of an adsorbed benzoate, not simple oxygen insertion into the carbene to form benzyl benzyloxy. At higher O pre-coverages benzoic acid forms between 400 and 500 K.
Graphical Abstract</description><identifier>ISSN: 1011-372X</identifier><identifier>EISSN: 1572-879X</identifier><identifier>DOI: 10.1007/s10562-018-2407-3</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Activated carbon ; Atomic oxygen ; Benzoates ; Benzoic acid ; Catalysis ; Chemistry ; Chemistry and Materials Science ; Industrial Chemistry/Chemical Engineering ; Organic acids ; Organometallic Chemistry ; Physical Chemistry ; Room temperature ; Titration ; Toluene ; Vapor phases</subject><ispartof>Catalysis letters, 2018-07, Vol.148 (7), p.1985-1989</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2018</rights><rights>COPYRIGHT 2018 Springer</rights><rights>Springer Science+Business Media, LLC, part of Springer Nature 2018.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c481t-fa7182710803a3767074853adbb6e86950b27f6c7434cce66e37081c329cb1fe3</citedby><cites>FETCH-LOGICAL-c481t-fa7182710803a3767074853adbb6e86950b27f6c7434cce66e37081c329cb1fe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27923,27924</link.rule.ids><backlink>$$Uhttps://www.osti.gov/biblio/1537730$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Rodríguez-Reyes, Juan Carlos F.</creatorcontrib><creatorcontrib>Friend, Cynthia M.</creatorcontrib><creatorcontrib>Madix, Robert J.</creatorcontrib><creatorcontrib>Harvard Univ., Cambridge, MA (United States)</creatorcontrib><title>Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold</title><title>Catalysis letters</title><addtitle>Catal Lett</addtitle><description>In accord with its gas phase acidity, toluene is activated by atomic oxygen adsorbed on Au(111) at the methyl C–H bonds. Titration of this species from the surface with HCOOD yields C
6
H
5
CHD
2
, indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low surface coverages of atomic oxygen the thusly-activated species yields only CO, CO
2
and water as gas phase products when heated above room temperature, indicating the facile formation of an adsorbed benzoate, not simple oxygen insertion into the carbene to form benzyl benzyloxy. At higher O pre-coverages benzoic acid forms between 400 and 500 K.
Graphical Abstract</description><subject>Activated carbon</subject><subject>Atomic oxygen</subject><subject>Benzoates</subject><subject>Benzoic acid</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Organic acids</subject><subject>Organometallic Chemistry</subject><subject>Physical Chemistry</subject><subject>Room temperature</subject><subject>Titration</subject><subject>Toluene</subject><subject>Vapor phases</subject><issn>1011-372X</issn><issn>1572-879X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kcFq3DAQhk1poWnaB-jNtKcenI40siUft0ubBBISkhRyE7J2vFHwSqmlLdlb36Fv2CepjANhoUWHEcP3aTT8RfGewREDkJ8jg7rhFTBVcQGywhfFAaslr5Rsb1_mOzBWoeS3r4s3Md4DQCtZe1BcXtNANrmfVC6mYpILvgx9eU7pbjeUyz-_fp-UX4Jfxal7E4YteSq7XXnxuFtTRv2EmmFwtjwOw-pt8ao3Q6R3T_Ww-P7t683ypDq7OD5dLs4qKxRLVW8kU1wyUIAGZSNBClWjWXVdQ6ppa-i47BsrBQprqWkIJShmkbe2Yz3hYfFhfjfE5HS0LpG9s8H7vI1mNUqJkKGPM_Qwhh9biknfh-3o8780FwgcG6zVM7U2A2nn-5BGYzcuWr2oBbYoBLBMHf2DymdFG5cHU-9yf0_4tCdkJtFjWpttjPr0-mqfZTNrxxDjSL1-GN3GjDvNQE8B6zlgnQPWU8Aas8NnJ2bWr2l8Xu7_0l8CqaPt</recordid><startdate>20180701</startdate><enddate>20180701</enddate><creator>Rodríguez-Reyes, Juan Carlos F.</creator><creator>Friend, Cynthia M.</creator><creator>Madix, Robert J.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>OTOTI</scope></search><sort><creationdate>20180701</creationdate><title>Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold</title><author>Rodríguez-Reyes, Juan Carlos F. ; Friend, Cynthia M. ; Madix, Robert J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c481t-fa7182710803a3767074853adbb6e86950b27f6c7434cce66e37081c329cb1fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Activated carbon</topic><topic>Atomic oxygen</topic><topic>Benzoates</topic><topic>Benzoic acid</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Organic acids</topic><topic>Organometallic Chemistry</topic><topic>Physical Chemistry</topic><topic>Room temperature</topic><topic>Titration</topic><topic>Toluene</topic><topic>Vapor phases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rodríguez-Reyes, Juan Carlos F.</creatorcontrib><creatorcontrib>Friend, Cynthia M.</creatorcontrib><creatorcontrib>Madix, Robert J.</creatorcontrib><creatorcontrib>Harvard Univ., Cambridge, MA (United States)</creatorcontrib><collection>CrossRef</collection><collection>Gale In Context: Science</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection (Proquest) (PQ_SDU_P3)</collection><collection>https://resources.nclive.org/materials</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>OSTI.GOV</collection><jtitle>Catalysis letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rodríguez-Reyes, Juan Carlos F.</au><au>Friend, Cynthia M.</au><au>Madix, Robert J.</au><aucorp>Harvard Univ., Cambridge, MA (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold</atitle><jtitle>Catalysis letters</jtitle><stitle>Catal Lett</stitle><date>2018-07-01</date><risdate>2018</risdate><volume>148</volume><issue>7</issue><spage>1985</spage><epage>1989</epage><pages>1985-1989</pages><issn>1011-372X</issn><eissn>1572-879X</eissn><abstract>In accord with its gas phase acidity, toluene is activated by atomic oxygen adsorbed on Au(111) at the methyl C–H bonds. Titration of this species from the surface with HCOOD yields C
6
H
5
CHD
2
, indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low surface coverages of atomic oxygen the thusly-activated species yields only CO, CO
2
and water as gas phase products when heated above room temperature, indicating the facile formation of an adsorbed benzoate, not simple oxygen insertion into the carbene to form benzyl benzyloxy. At higher O pre-coverages benzoic acid forms between 400 and 500 K.
Graphical Abstract</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10562-018-2407-3</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1011-372X |
| ispartof | Catalysis letters, 2018-07, Vol.148 (7), p.1985-1989 |
| issn | 1011-372X 1572-879X |
| language | eng |
| recordid | cdi_osti_scitechconnect_1537730 |
| source | Springer Link |
| subjects | Activated carbon Atomic oxygen Benzoates Benzoic acid Catalysis Chemistry Chemistry and Materials Science Industrial Chemistry/Chemical Engineering Organic acids Organometallic Chemistry Physical Chemistry Room temperature Titration Toluene Vapor phases |
| title | Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold |
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