An explicit account of solvation is essential for modeling Suzuki-Miyaura coupling in protic solvents
We compared explicit and implicit solvation approaches in modeling the free energy profile of the final step of Suzuki-Miyaura coupling. Both approaches produced similar ΔG(≠) in all the studied solvents (benzene, toluene, DMF, ethanol, and water). Solvation free energies of individual reaction comp...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2015-01, Vol.44 (40), p.17795-17799 |
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| container_issue | 40 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 44 |
| creator | Zeifman, Alexey A Novikov, Fedor N Stroylov, Victor S Stroganov, Oleg V Svitanko, Igor V Chilov, Ghermes G |
| description | We compared explicit and implicit solvation approaches in modeling the free energy profile of the final step of Suzuki-Miyaura coupling. Both approaches produced similar ΔG(≠) in all the studied solvents (benzene, toluene, DMF, ethanol, and water). Solvation free energies of individual reaction components reasonably correlated for explicit and implicit models in aprotic solvents (RMSE = 30-50 kJ mol(-1), R(2) > 0.71). However for ethanol and water the correlation was poor. We attributed this difference to the formation of the PdH-O hydrogen bond with Pd(PPh3)2 which was surprisingly observed in explicit modeling. Further QM calculations of the Pd(PPh3)2-H2O system confirmed the direction (PdH) and stability of this bonding. Therefore we stress the need for considering explicit solvation for modeling Pd-catalyzed reactions in protic solvents. |
| doi_str_mv | 10.1039/c5dt03126e |
| format | Article |
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Both approaches produced similar ΔG(≠) in all the studied solvents (benzene, toluene, DMF, ethanol, and water). Solvation free energies of individual reaction components reasonably correlated for explicit and implicit models in aprotic solvents (RMSE = 30-50 kJ mol(-1), R(2) > 0.71). However for ethanol and water the correlation was poor. We attributed this difference to the formation of the PdH-O hydrogen bond with Pd(PPh3)2 which was surprisingly observed in explicit modeling. Further QM calculations of the Pd(PPh3)2-H2O system confirmed the direction (PdH) and stability of this bonding. 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Both approaches produced similar ΔG(≠) in all the studied solvents (benzene, toluene, DMF, ethanol, and water). Solvation free energies of individual reaction components reasonably correlated for explicit and implicit models in aprotic solvents (RMSE = 30-50 kJ mol(-1), R(2) > 0.71). However for ethanol and water the correlation was poor. We attributed this difference to the formation of the PdH-O hydrogen bond with Pd(PPh3)2 which was surprisingly observed in explicit modeling. Further QM calculations of the Pd(PPh3)2-H2O system confirmed the direction (PdH) and stability of this bonding. Therefore we stress the need for considering explicit solvation for modeling Pd-catalyzed reactions in protic solvents.</description><subject>Bonding</subject><subject>Correlation</subject><subject>Ethanol</subject><subject>Ethyl alcohol</subject><subject>Free energy</subject><subject>Joining</subject><subject>Solvation</subject><subject>Solvents</subject><subject>Toluene</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqNUclOwzAQtRCIlsKFD0A-IqSA40ns5FiVskggDpRz5DhjZEjiEjuI8vWEtvTMaRa9ZTSPkNOYXcYM8iudVoFBzAXukXGcSBnlHJL9Xc_FiBx5_8YY5yzlh2TEBeQ5sGRMcNpS_FrWVttAldaubwN1hnpXf6pgXUutp-g9tsGqmhrX0cZVWNv2lT733_27jR7tSvWdogN3ud7bli47F6xeqwxMf0wOjKo9nmzrhLzczBezu-jh6fZ-Nn2INHAWojLP1HCgkJAllYRSGJVr1EyUJhNZKQ0HlSBXGeQwzFVlkiw2hiksAQxWMCHnG93B_6NHH4rGeo11rVp0vS9iKTiTGaT8H1DOkkSmg9WEXGygunPed2iKZWcb1a2KmBW_CRSz9HqxTmA-gM-2un3ZYLWD_r0cfgDyqIKb</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Zeifman, Alexey A</creator><creator>Novikov, Fedor N</creator><creator>Stroylov, Victor S</creator><creator>Stroganov, Oleg V</creator><creator>Svitanko, Igor V</creator><creator>Chilov, Ghermes G</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150101</creationdate><title>An explicit account of solvation is essential for modeling Suzuki-Miyaura coupling in protic solvents</title><author>Zeifman, Alexey A ; Novikov, Fedor N ; Stroylov, Victor S ; Stroganov, Oleg V ; Svitanko, Igor V ; Chilov, Ghermes G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-b98a05267384d73b6fa9cec06bf868b7f23a4e2a839368bddf481ff0aeb33fed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Bonding</topic><topic>Correlation</topic><topic>Ethanol</topic><topic>Ethyl alcohol</topic><topic>Free energy</topic><topic>Joining</topic><topic>Solvation</topic><topic>Solvents</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zeifman, Alexey A</creatorcontrib><creatorcontrib>Novikov, Fedor N</creatorcontrib><creatorcontrib>Stroylov, Victor S</creatorcontrib><creatorcontrib>Stroganov, Oleg V</creatorcontrib><creatorcontrib>Svitanko, Igor V</creatorcontrib><creatorcontrib>Chilov, Ghermes G</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</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><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zeifman, Alexey A</au><au>Novikov, Fedor N</au><au>Stroylov, Victor S</au><au>Stroganov, Oleg V</au><au>Svitanko, Igor V</au><au>Chilov, Ghermes G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An explicit account of solvation is essential for modeling Suzuki-Miyaura coupling in protic solvents</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2015-01-01</date><risdate>2015</risdate><volume>44</volume><issue>40</issue><spage>17795</spage><epage>17799</epage><pages>17795-17799</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>We compared explicit and implicit solvation approaches in modeling the free energy profile of the final step of Suzuki-Miyaura coupling. 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| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2015-01, Vol.44 (40), p.17795-17799 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Bonding Correlation Ethanol Ethyl alcohol Free energy Joining Solvation Solvents Toluene |
| title | An explicit account of solvation is essential for modeling Suzuki-Miyaura coupling in protic solvents |
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