Energetics and structural properties of neutral and deprotonated phenyl carbinols
•We determined ΔfHm0(g) of neutral and deprotonated (in the OH group) phenyl-carbinols.•DFT/M05-2X is a good method to estimate ΔfHm0(g) and GA values for phenyl carbinols.•α-alkyl, phenyl and CF3 substituents in methanol significantly enhance the acidity. Theoretical and experimental studies on the...
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| Veröffentlicht in: | The Journal of chemical thermodynamics 2016-06, Vol.97, p.315-321 |
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| container_title | The Journal of chemical thermodynamics |
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| creator | Dávalos, Juan Z. Guerrero, Andrés Valderrama-Negrón, Ana C. Romero, Violeta Lago, Alexsandre F. |
| description | •We determined ΔfHm0(g) of neutral and deprotonated (in the OH group) phenyl-carbinols.•DFT/M05-2X is a good method to estimate ΔfHm0(g) and GA values for phenyl carbinols.•α-alkyl, phenyl and CF3 substituents in methanol significantly enhance the acidity.
Theoretical and experimental studies on the energetics, structure and other physicochemical properties of neutral 1-phenylethanol (1OH), diphenylmethanol (2OH) and triphenylmethanol (3OH) and their corresponding deprotonated anions (oxyanions, formed by deprotonation of the OH group) are reported in this work. The standard enthalpies of formation in the gas phase at T=298.15K, ΔfHm0(g) have been determined. Quantum chemical calculations, at the DFT (particularly M05-2X method) and in some cases at the ab initio (G3) levels, have shed light on structural and electronic effects on the thermodynamic stability and intrinsic acidity of the studied compounds. These calculations confirmed the excellent consistency of the experimental results. |
| doi_str_mv | 10.1016/j.jct.2016.02.010 |
| format | Article |
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Theoretical and experimental studies on the energetics, structure and other physicochemical properties of neutral 1-phenylethanol (1OH), diphenylmethanol (2OH) and triphenylmethanol (3OH) and their corresponding deprotonated anions (oxyanions, formed by deprotonation of the OH group) are reported in this work. The standard enthalpies of formation in the gas phase at T=298.15K, ΔfHm0(g) have been determined. Quantum chemical calculations, at the DFT (particularly M05-2X method) and in some cases at the ab initio (G3) levels, have shed light on structural and electronic effects on the thermodynamic stability and intrinsic acidity of the studied compounds. These calculations confirmed the excellent consistency of the experimental results.</description><identifier>ISSN: 0021-9614</identifier><identifier>EISSN: 1096-3626</identifier><identifier>DOI: 10.1016/j.jct.2016.02.010</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Anions ; Combustion ; Consistency ; DFT(M05) ; Enthalpy of formation ; Gas phases ; Intrinsic acidity ; Mathematical analysis ; Phenyl carbinols ; Phenyls ; Stability ; Sublimation ; Thermodynamics</subject><ispartof>The Journal of chemical thermodynamics, 2016-06, Vol.97, p.315-321</ispartof><rights>2016 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c367t-f2447d868f4943c11c0aef7b55ade87107faf5019db8137873065bc94d7372c33</citedby><cites>FETCH-LOGICAL-c367t-f2447d868f4943c11c0aef7b55ade87107faf5019db8137873065bc94d7372c33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jct.2016.02.010$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Dávalos, Juan Z.</creatorcontrib><creatorcontrib>Guerrero, Andrés</creatorcontrib><creatorcontrib>Valderrama-Negrón, Ana C.</creatorcontrib><creatorcontrib>Romero, Violeta</creatorcontrib><creatorcontrib>Lago, Alexsandre F.</creatorcontrib><title>Energetics and structural properties of neutral and deprotonated phenyl carbinols</title><title>The Journal of chemical thermodynamics</title><description>•We determined ΔfHm0(g) of neutral and deprotonated (in the OH group) phenyl-carbinols.•DFT/M05-2X is a good method to estimate ΔfHm0(g) and GA values for phenyl carbinols.•α-alkyl, phenyl and CF3 substituents in methanol significantly enhance the acidity.
Theoretical and experimental studies on the energetics, structure and other physicochemical properties of neutral 1-phenylethanol (1OH), diphenylmethanol (2OH) and triphenylmethanol (3OH) and their corresponding deprotonated anions (oxyanions, formed by deprotonation of the OH group) are reported in this work. The standard enthalpies of formation in the gas phase at T=298.15K, ΔfHm0(g) have been determined. Quantum chemical calculations, at the DFT (particularly M05-2X method) and in some cases at the ab initio (G3) levels, have shed light on structural and electronic effects on the thermodynamic stability and intrinsic acidity of the studied compounds. These calculations confirmed the excellent consistency of the experimental results.</description><subject>Anions</subject><subject>Combustion</subject><subject>Consistency</subject><subject>DFT(M05)</subject><subject>Enthalpy of formation</subject><subject>Gas phases</subject><subject>Intrinsic acidity</subject><subject>Mathematical analysis</subject><subject>Phenyl carbinols</subject><subject>Phenyls</subject><subject>Stability</subject><subject>Sublimation</subject><subject>Thermodynamics</subject><issn>0021-9614</issn><issn>1096-3626</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kE9LxDAQxYMouK5-AG89emmdNG3S4kmW9Q8siKDnkCZTTemma5IKfntT1rOnGWbeG-b9CLmmUFCg_HYoBh2LMrUFlAVQOCErCi3PGS_5KVkBlDRvOa3OyUUIAwC0rIUVed069B8YrQ6ZciYL0c86zl6N2cFPB_TRYsimPnM4x2W6iAymXZycimiywye6nzHTynfWTWO4JGe9GgNe_dU1eX_Yvm2e8t3L4_PmfpdrxkXM-7KqhGl401dtxTSlGhT2oqtrZbARFESv-hpoa7qGMtEIBrzudFsZwUSpGVuTm-Pd9MvXjCHKvQ0ax1E5nOYgaUN5islYm6T0KNV-CsFjLw_e7pX_kRTkgk8OMuGTCz4JpUz4kufu6MGU4duil0FbdBqN9Zi0ZrL_uH8BDCV4qQ</recordid><startdate>20160601</startdate><enddate>20160601</enddate><creator>Dávalos, Juan Z.</creator><creator>Guerrero, Andrés</creator><creator>Valderrama-Negrón, Ana C.</creator><creator>Romero, Violeta</creator><creator>Lago, Alexsandre F.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20160601</creationdate><title>Energetics and structural properties of neutral and deprotonated phenyl carbinols</title><author>Dávalos, Juan Z. ; Guerrero, Andrés ; Valderrama-Negrón, Ana C. ; Romero, Violeta ; Lago, Alexsandre F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-f2447d868f4943c11c0aef7b55ade87107faf5019db8137873065bc94d7372c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Anions</topic><topic>Combustion</topic><topic>Consistency</topic><topic>DFT(M05)</topic><topic>Enthalpy of formation</topic><topic>Gas phases</topic><topic>Intrinsic acidity</topic><topic>Mathematical analysis</topic><topic>Phenyl carbinols</topic><topic>Phenyls</topic><topic>Stability</topic><topic>Sublimation</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dávalos, Juan Z.</creatorcontrib><creatorcontrib>Guerrero, Andrés</creatorcontrib><creatorcontrib>Valderrama-Negrón, Ana C.</creatorcontrib><creatorcontrib>Romero, Violeta</creatorcontrib><creatorcontrib>Lago, Alexsandre F.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>The Journal of chemical thermodynamics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dávalos, Juan Z.</au><au>Guerrero, Andrés</au><au>Valderrama-Negrón, Ana C.</au><au>Romero, Violeta</au><au>Lago, Alexsandre F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Energetics and structural properties of neutral and deprotonated phenyl carbinols</atitle><jtitle>The Journal of chemical thermodynamics</jtitle><date>2016-06-01</date><risdate>2016</risdate><volume>97</volume><spage>315</spage><epage>321</epage><pages>315-321</pages><issn>0021-9614</issn><eissn>1096-3626</eissn><abstract>•We determined ΔfHm0(g) of neutral and deprotonated (in the OH group) phenyl-carbinols.•DFT/M05-2X is a good method to estimate ΔfHm0(g) and GA values for phenyl carbinols.•α-alkyl, phenyl and CF3 substituents in methanol significantly enhance the acidity.
Theoretical and experimental studies on the energetics, structure and other physicochemical properties of neutral 1-phenylethanol (1OH), diphenylmethanol (2OH) and triphenylmethanol (3OH) and their corresponding deprotonated anions (oxyanions, formed by deprotonation of the OH group) are reported in this work. The standard enthalpies of formation in the gas phase at T=298.15K, ΔfHm0(g) have been determined. Quantum chemical calculations, at the DFT (particularly M05-2X method) and in some cases at the ab initio (G3) levels, have shed light on structural and electronic effects on the thermodynamic stability and intrinsic acidity of the studied compounds. These calculations confirmed the excellent consistency of the experimental results.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.jct.2016.02.010</doi><tpages>7</tpages></addata></record> |
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| subjects | Anions Combustion Consistency DFT(M05) Enthalpy of formation Gas phases Intrinsic acidity Mathematical analysis Phenyl carbinols Phenyls Stability Sublimation Thermodynamics |
| title | Energetics and structural properties of neutral and deprotonated phenyl carbinols |
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