Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives
The electron delocalization of benzene (C6H6) and hexafluorobenzene (C6F6) was analyzed in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). The computed out‐of‐plane component of the induced magnetic field at a distance (r) greater than...
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| Veröffentlicht in: | ChemistryOpen (Weinheim) 2015-06, Vol.4 (3), p.302-307 |
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| creator | Torres‐Vega, Juan J. Vásquez‐Espinal, Alejandro Ruiz, Lina Fernández‐Herrera, María A. Alvarez‐Thon, Luis Merino, Gabriel Tiznado, William |
| description | The electron delocalization of benzene (C6H6) and hexafluorobenzene (C6F6) was analyzed in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). The computed out‐of‐plane component of the induced magnetic field at a distance (r) greater than or equal to 1.0 Å above the ring center correlates well (R2>0.99) with the RCS value. According to these criteria, fluorination has two effects on the C6 skeleton; concomitantly, the resonant effects diminish the π electron delocalization and the inductive effects decrease the charge density at the ring center and therefore reduce the magnitude of the paratropic current generated in this region. The equilibrium between both effects decreases aromaticity in the fluorinated benzene derivatives. These results can be extrapolated to determine the aromaticity of any derivative within the series of fluorinated benzene derivatives (C6H(6−n)Fn, where n=1–5).
Determining aromaticity: Here, we analyzed the electron delocalization in fluorinated benzene derivatives (C6H(6−n)Fn) in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). Fluorination was found to decrease the paratropic ring current through inductive effects and to decrease the diatropic ring current through resonance effects, and the balance between these two effects decreases aromaticity with increased fluorination. |
| doi_str_mv | 10.1002/open.201402110 |
| format | Article |
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Determining aromaticity: Here, we analyzed the electron delocalization in fluorinated benzene derivatives (C6H(6−n)Fn) in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). Fluorination was found to decrease the paratropic ring current through inductive effects and to decrease the diatropic ring current through resonance effects, and the balance between these two effects decreases aromaticity with increased fluorination.</description><identifier>ISSN: 2191-1363</identifier><identifier>EISSN: 2191-1363</identifier><identifier>DOI: 10.1002/open.201402110</identifier><identifier>PMID: 26246992</identifier><language>eng</language><publisher>Germany: John Wiley & Sons, Inc</publisher><subject>adaptive natural partitioning analysis ; Aromaticity ; Benzene ; Bonding strength ; Charge density ; Chemical bonds ; Chemical equilibrium ; Derivatives ; Extrapolation ; fluorinated benzenes ; Fluorination ; induced magnetic fields ; Magnetic fields ; magnetically induced current density ; Ring currents ; Strength</subject><ispartof>ChemistryOpen (Weinheim), 2015-06, Vol.4 (3), p.302-307</ispartof><rights>2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2015. This work is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6410-93491e43f5885c40c4de7fcbca613002f33e33e19ba7f7fd8eeb89585434d1373</citedby><cites>FETCH-LOGICAL-c6410-93491e43f5885c40c4de7fcbca613002f33e33e19ba7f7fd8eeb89585434d1373</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4522180/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4522180/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,1411,11541,27901,27902,45550,45551,46027,46451,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26246992$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Torres‐Vega, Juan J.</creatorcontrib><creatorcontrib>Vásquez‐Espinal, Alejandro</creatorcontrib><creatorcontrib>Ruiz, Lina</creatorcontrib><creatorcontrib>Fernández‐Herrera, María A.</creatorcontrib><creatorcontrib>Alvarez‐Thon, Luis</creatorcontrib><creatorcontrib>Merino, Gabriel</creatorcontrib><creatorcontrib>Tiznado, William</creatorcontrib><title>Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives</title><title>ChemistryOpen (Weinheim)</title><addtitle>ChemistryOpen</addtitle><description>The electron delocalization of benzene (C6H6) and hexafluorobenzene (C6F6) was analyzed in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). The computed out‐of‐plane component of the induced magnetic field at a distance (r) greater than or equal to 1.0 Å above the ring center correlates well (R2>0.99) with the RCS value. According to these criteria, fluorination has two effects on the C6 skeleton; concomitantly, the resonant effects diminish the π electron delocalization and the inductive effects decrease the charge density at the ring center and therefore reduce the magnitude of the paratropic current generated in this region. The equilibrium between both effects decreases aromaticity in the fluorinated benzene derivatives. These results can be extrapolated to determine the aromaticity of any derivative within the series of fluorinated benzene derivatives (C6H(6−n)Fn, where n=1–5).
Determining aromaticity: Here, we analyzed the electron delocalization in fluorinated benzene derivatives (C6H(6−n)Fn) in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). Fluorination was found to decrease the paratropic ring current through inductive effects and to decrease the diatropic ring current through resonance effects, and the balance between these two effects decreases aromaticity with increased fluorination.</description><subject>adaptive natural partitioning analysis</subject><subject>Aromaticity</subject><subject>Benzene</subject><subject>Bonding strength</subject><subject>Charge density</subject><subject>Chemical bonds</subject><subject>Chemical equilibrium</subject><subject>Derivatives</subject><subject>Extrapolation</subject><subject>fluorinated benzenes</subject><subject>Fluorination</subject><subject>induced magnetic fields</subject><subject>Magnetic fields</subject><subject>magnetically induced current density</subject><subject>Ring currents</subject><subject>Strength</subject><issn>2191-1363</issn><issn>2191-1363</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>BENPR</sourceid><recordid>eNqFkUtLxDAURoMoKurWpRTcuJkxr6bpRtDxCaIiug6Z9FYjbTIm7cj4680wOj42hkACOfdwbz6EdgkeEozpoZ-AG1JMOKaE4BW0SUlJBoQJtvrjvoF2YnzBaRW8JLlYRxtUUC7Kkm6im3uY2mg7656y4-Bb3Vlju1mmXZWNnqG1RjfZiXfVHPB1dt70PlinO6iyE3Dv4CA7hWCnqXAKcRut1bqJsPN5bqHH87OH0eXg-vbianR8PTCCEzwoWeoEOKtzKXPDseEVFLUZGy0IS5PVjEHapBzroi7qSgKMZZnLnDNeEVawLXS08E76cQuVAdcF3ahJsK0OM-W1Vb9fnH1WT36qeE4pkTgJDj4Fwb_2EDvV2migabQD30eVGJxYTun_aIGpyAWnIqH7f9AX3weXfkIxLCXLaYFlooYLygQfY4B62TfBah6smgerlsGmgr2f0y7xrxgTUC6AN9vA7B-dur07u_mWfwCaxq71</recordid><startdate>201506</startdate><enddate>201506</enddate><creator>Torres‐Vega, Juan J.</creator><creator>Vásquez‐Espinal, Alejandro</creator><creator>Ruiz, Lina</creator><creator>Fernández‐Herrera, María A.</creator><creator>Alvarez‐Thon, Luis</creator><creator>Merino, Gabriel</creator><creator>Tiznado, William</creator><general>John Wiley & Sons, Inc</general><general>John Wiley & Sons, Ltd</general><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>L6V</scope><scope>L7M</scope><scope>M7S</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>201506</creationdate><title>Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives</title><author>Torres‐Vega, Juan J. ; Vásquez‐Espinal, Alejandro ; Ruiz, Lina ; Fernández‐Herrera, María A. ; Alvarez‐Thon, Luis ; Merino, Gabriel ; Tiznado, William</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6410-93491e43f5885c40c4de7fcbca613002f33e33e19ba7f7fd8eeb89585434d1373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>adaptive natural partitioning analysis</topic><topic>Aromaticity</topic><topic>Benzene</topic><topic>Bonding strength</topic><topic>Charge density</topic><topic>Chemical bonds</topic><topic>Chemical equilibrium</topic><topic>Derivatives</topic><topic>Extrapolation</topic><topic>fluorinated benzenes</topic><topic>Fluorination</topic><topic>induced magnetic fields</topic><topic>Magnetic fields</topic><topic>magnetically induced current density</topic><topic>Ring currents</topic><topic>Strength</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Torres‐Vega, Juan J.</creatorcontrib><creatorcontrib>Vásquez‐Espinal, Alejandro</creatorcontrib><creatorcontrib>Ruiz, Lina</creatorcontrib><creatorcontrib>Fernández‐Herrera, María A.</creatorcontrib><creatorcontrib>Alvarez‐Thon, Luis</creatorcontrib><creatorcontrib>Merino, Gabriel</creatorcontrib><creatorcontrib>Tiznado, William</creatorcontrib><collection>Wiley Online Library Open Access</collection><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>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>ProQuest Engineering Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Engineering Database</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content Database</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>Engineering Collection</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>ChemistryOpen (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Torres‐Vega, Juan J.</au><au>Vásquez‐Espinal, Alejandro</au><au>Ruiz, Lina</au><au>Fernández‐Herrera, María A.</au><au>Alvarez‐Thon, Luis</au><au>Merino, Gabriel</au><au>Tiznado, William</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives</atitle><jtitle>ChemistryOpen (Weinheim)</jtitle><addtitle>ChemistryOpen</addtitle><date>2015-06</date><risdate>2015</risdate><volume>4</volume><issue>3</issue><spage>302</spage><epage>307</epage><pages>302-307</pages><issn>2191-1363</issn><eissn>2191-1363</eissn><abstract>The electron delocalization of benzene (C6H6) and hexafluorobenzene (C6F6) was analyzed in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). The computed out‐of‐plane component of the induced magnetic field at a distance (r) greater than or equal to 1.0 Å above the ring center correlates well (R2>0.99) with the RCS value. According to these criteria, fluorination has two effects on the C6 skeleton; concomitantly, the resonant effects diminish the π electron delocalization and the inductive effects decrease the charge density at the ring center and therefore reduce the magnitude of the paratropic current generated in this region. The equilibrium between both effects decreases aromaticity in the fluorinated benzene derivatives. These results can be extrapolated to determine the aromaticity of any derivative within the series of fluorinated benzene derivatives (C6H(6−n)Fn, where n=1–5).
Determining aromaticity: Here, we analyzed the electron delocalization in fluorinated benzene derivatives (C6H(6−n)Fn) in terms of the induced magnetic field, nucleus‐independent chemical shift (NICS), and ring current strength (RCS). Fluorination was found to decrease the paratropic ring current through inductive effects and to decrease the diatropic ring current through resonance effects, and the balance between these two effects decreases aromaticity with increased fluorination.</abstract><cop>Germany</cop><pub>John Wiley & Sons, Inc</pub><pmid>26246992</pmid><doi>10.1002/open.201402110</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | adaptive natural partitioning analysis Aromaticity Benzene Bonding strength Charge density Chemical bonds Chemical equilibrium Derivatives Extrapolation fluorinated benzenes Fluorination induced magnetic fields Magnetic fields magnetically induced current density Ring currents Strength |
| title | Revisiting Aromaticity and Chemical Bonding of Fluorinated Benzene Derivatives |
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