para‑Xylyl bis‑1‑methylimidazolium bis(trifluoromethanesulfonyl)imide: Synthesis, crystal structure, thermal stability, vibrational studies

In this study, a new para‑xylyl linked di‑imidazolium [p‑C6H4(CH2ImMe)2+] ionic liquid (DIL) containing the bis(trifluoromethanesulfonyl)imide [(CF3SO2)2N−] anion is synthesized. The method is based on the alkylation reaction of 1‑methyl imidazole, followed by anion exchange. The obtained DIL is cha...

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Veröffentlicht in:Journal of molecular liquids 2018-06, Vol.260, p.391-402
Hauptverfasser: Haddad, Boumediene, Paolone, Annalisa, Villemin, Didier, Lohier, Jean-François, Drai, Mokhtar, Bresson, Serge, Abbas, Ouissam, Belarbi, El-habib
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container_issue
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container_title Journal of molecular liquids
container_volume 260
creator Haddad, Boumediene
Paolone, Annalisa
Villemin, Didier
Lohier, Jean-François
Drai, Mokhtar
Bresson, Serge
Abbas, Ouissam
Belarbi, El-habib
description In this study, a new para‑xylyl linked di‑imidazolium [p‑C6H4(CH2ImMe)2+] ionic liquid (DIL) containing the bis(trifluoromethanesulfonyl)imide [(CF3SO2)2N−] anion is synthesized. The method is based on the alkylation reaction of 1‑methyl imidazole, followed by anion exchange. The obtained DIL is characterized by 1H NMR, 13C NMR, 19F NMR and FT-IR spectroscopy. The melting point and the subsequent decomposition of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 are measured by using differential scanning calorimetry (DSC) and thermogravimetric (TGA) analyses in the temperature range from 25 to 700°C. Thermal analysis indicated that this DIL melted below 100°C and can, therefore, be classified as an ionic liquid. Vibrational spectroscopy studies were conducted by infrared (IR), Raman (FT-Raman) spectroscopy and DFT calculations. Moreover, the crystal structure is investigated by single crystal X-ray diffraction (XRD) method. The X-ray studies on [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 show that it crystallizes in the monoclinic system with space group P21/c. The theoretical structural parameters such as bond lengths, bond angles and dihedral angles determined by DFT methods are in good agreement with the XRD results. [Display omitted] •Synthesis and crystal structure of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Thermal stability of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Only the trans conformers of both cation and anion are present.•Interaction between [p‑C6H4(CH2ImMe)2] and [(CF3SO2)2N−]
doi_str_mv 10.1016/j.molliq.2018.03.113
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The method is based on the alkylation reaction of 1‑methyl imidazole, followed by anion exchange. The obtained DIL is characterized by 1H NMR, 13C NMR, 19F NMR and FT-IR spectroscopy. The melting point and the subsequent decomposition of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 are measured by using differential scanning calorimetry (DSC) and thermogravimetric (TGA) analyses in the temperature range from 25 to 700°C. Thermal analysis indicated that this DIL melted below 100°C and can, therefore, be classified as an ionic liquid. Vibrational spectroscopy studies were conducted by infrared (IR), Raman (FT-Raman) spectroscopy and DFT calculations. Moreover, the crystal structure is investigated by single crystal X-ray diffraction (XRD) method. The X-ray studies on [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 show that it crystallizes in the monoclinic system with space group P21/c. The theoretical structural parameters such as bond lengths, bond angles and dihedral angles determined by DFT methods are in good agreement with the XRD results. [Display omitted] •Synthesis and crystal structure of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Thermal stability of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Only the trans conformers of both cation and anion are present.•Interaction between [p‑C6H4(CH2ImMe)2] and [(CF3SO2)2N−]</description><identifier>ISSN: 0167-7322</identifier><identifier>EISSN: 1873-3166</identifier><identifier>DOI: 10.1016/j.molliq.2018.03.113</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Bis(trifluoromethanesulfonyl)imide ; Chemical Sciences ; Crystal structure ; DFT ; Di‑imidazolium ; or physical chemistry ; Organic chemistry ; para‑Xylyl ; Raman measurements ; Theoretical and ; Thermal stability ; Vibrational spectra</subject><ispartof>Journal of molecular liquids, 2018-06, Vol.260, p.391-402</ispartof><rights>2018 Elsevier B.V.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c377t-2907b53e284ba0cd045e38d9de3b9f466fc5d205da4029ca00c69c4786e4719d3</citedby><cites>FETCH-LOGICAL-c377t-2907b53e284ba0cd045e38d9de3b9f466fc5d205da4029ca00c69c4786e4719d3</cites><orcidid>0000-0002-4839-7815 ; 0000-0003-0932-0468 ; 0000-0001-6339-4797 ; 0000-0002-6266-3817 ; 0000-0001-9198-9528</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.molliq.2018.03.113$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://hal.science/hal-01829548$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Haddad, Boumediene</creatorcontrib><creatorcontrib>Paolone, Annalisa</creatorcontrib><creatorcontrib>Villemin, Didier</creatorcontrib><creatorcontrib>Lohier, Jean-François</creatorcontrib><creatorcontrib>Drai, Mokhtar</creatorcontrib><creatorcontrib>Bresson, Serge</creatorcontrib><creatorcontrib>Abbas, Ouissam</creatorcontrib><creatorcontrib>Belarbi, El-habib</creatorcontrib><title>para‑Xylyl bis‑1‑methylimidazolium bis(trifluoromethanesulfonyl)imide: Synthesis, crystal structure, thermal stability, vibrational studies</title><title>Journal of molecular liquids</title><description>In this study, a new para‑xylyl linked di‑imidazolium [p‑C6H4(CH2ImMe)2+] ionic liquid (DIL) containing the bis(trifluoromethanesulfonyl)imide [(CF3SO2)2N−] anion is synthesized. The method is based on the alkylation reaction of 1‑methyl imidazole, followed by anion exchange. The obtained DIL is characterized by 1H NMR, 13C NMR, 19F NMR and FT-IR spectroscopy. The melting point and the subsequent decomposition of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 are measured by using differential scanning calorimetry (DSC) and thermogravimetric (TGA) analyses in the temperature range from 25 to 700°C. Thermal analysis indicated that this DIL melted below 100°C and can, therefore, be classified as an ionic liquid. Vibrational spectroscopy studies were conducted by infrared (IR), Raman (FT-Raman) spectroscopy and DFT calculations. Moreover, the crystal structure is investigated by single crystal X-ray diffraction (XRD) method. The X-ray studies on [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 show that it crystallizes in the monoclinic system with space group P21/c. The theoretical structural parameters such as bond lengths, bond angles and dihedral angles determined by DFT methods are in good agreement with the XRD results. [Display omitted] •Synthesis and crystal structure of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Thermal stability of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Only the trans conformers of both cation and anion are present.•Interaction between [p‑C6H4(CH2ImMe)2] and [(CF3SO2)2N−]</description><subject>Bis(trifluoromethanesulfonyl)imide</subject><subject>Chemical Sciences</subject><subject>Crystal structure</subject><subject>DFT</subject><subject>Di‑imidazolium</subject><subject>or physical chemistry</subject><subject>Organic chemistry</subject><subject>para‑Xylyl</subject><subject>Raman measurements</subject><subject>Theoretical and</subject><subject>Thermal stability</subject><subject>Vibrational spectra</subject><issn>0167-7322</issn><issn>1873-3166</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9Uc1q3DAQFqGBbJO8QQ4-NrB2R5Z_eyiE0DaBhRySQG5ClmR2FtlKJXnBOeUV8op5ksrZ0mMPwwzfz8DMR8gFhYwCrb7ussEag7-zHGiTAcsoZUdkRZuapYxW1SeyirI6rVmen5DP3u8AoCwbWJG3Z-HE--vb02xmk3To40xjDTpsZ4MDKvFiDU7Dwn0JDnszWWcXWozaT6a342wuF6H-ltzPY9hqj36dSDf7IEzig5tkmJxeJ5FywwckOjQY5nWyx86JgHb8gCeF2p-R414Yr8__9lPy-PPHw_VNurn7dXt9tUklq-uQ5i3UXcl03hSdAKmgKDVrVKs069q-qKpeliqHUokC8lYKAFm1sqibShc1bRU7JZeHvVth-LPDQbiZW4H85mrDFyz-Mm_LotnTqC0OWums9073_wwU-BIB3_FDBHyJgAPjMYJo-36w6XjHHrXjXqIepVbotAxcWfz_gj8i85j2</recordid><startdate>20180615</startdate><enddate>20180615</enddate><creator>Haddad, Boumediene</creator><creator>Paolone, Annalisa</creator><creator>Villemin, Didier</creator><creator>Lohier, Jean-François</creator><creator>Drai, Mokhtar</creator><creator>Bresson, Serge</creator><creator>Abbas, Ouissam</creator><creator>Belarbi, El-habib</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-4839-7815</orcidid><orcidid>https://orcid.org/0000-0003-0932-0468</orcidid><orcidid>https://orcid.org/0000-0001-6339-4797</orcidid><orcidid>https://orcid.org/0000-0002-6266-3817</orcidid><orcidid>https://orcid.org/0000-0001-9198-9528</orcidid></search><sort><creationdate>20180615</creationdate><title>para‑Xylyl bis‑1‑methylimidazolium bis(trifluoromethanesulfonyl)imide: Synthesis, crystal structure, thermal stability, vibrational studies</title><author>Haddad, Boumediene ; Paolone, Annalisa ; Villemin, Didier ; Lohier, Jean-François ; Drai, Mokhtar ; Bresson, Serge ; Abbas, Ouissam ; Belarbi, El-habib</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-2907b53e284ba0cd045e38d9de3b9f466fc5d205da4029ca00c69c4786e4719d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Bis(trifluoromethanesulfonyl)imide</topic><topic>Chemical Sciences</topic><topic>Crystal structure</topic><topic>DFT</topic><topic>Di‑imidazolium</topic><topic>or physical chemistry</topic><topic>Organic chemistry</topic><topic>para‑Xylyl</topic><topic>Raman measurements</topic><topic>Theoretical and</topic><topic>Thermal stability</topic><topic>Vibrational spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Haddad, Boumediene</creatorcontrib><creatorcontrib>Paolone, Annalisa</creatorcontrib><creatorcontrib>Villemin, Didier</creatorcontrib><creatorcontrib>Lohier, Jean-François</creatorcontrib><creatorcontrib>Drai, Mokhtar</creatorcontrib><creatorcontrib>Bresson, Serge</creatorcontrib><creatorcontrib>Abbas, Ouissam</creatorcontrib><creatorcontrib>Belarbi, El-habib</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of molecular liquids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Haddad, Boumediene</au><au>Paolone, Annalisa</au><au>Villemin, Didier</au><au>Lohier, Jean-François</au><au>Drai, Mokhtar</au><au>Bresson, Serge</au><au>Abbas, Ouissam</au><au>Belarbi, El-habib</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>para‑Xylyl bis‑1‑methylimidazolium bis(trifluoromethanesulfonyl)imide: Synthesis, crystal structure, thermal stability, vibrational studies</atitle><jtitle>Journal of molecular liquids</jtitle><date>2018-06-15</date><risdate>2018</risdate><volume>260</volume><spage>391</spage><epage>402</epage><pages>391-402</pages><issn>0167-7322</issn><eissn>1873-3166</eissn><abstract>In this study, a new para‑xylyl linked di‑imidazolium [p‑C6H4(CH2ImMe)2+] ionic liquid (DIL) containing the bis(trifluoromethanesulfonyl)imide [(CF3SO2)2N−] anion is synthesized. The method is based on the alkylation reaction of 1‑methyl imidazole, followed by anion exchange. The obtained DIL is characterized by 1H NMR, 13C NMR, 19F NMR and FT-IR spectroscopy. The melting point and the subsequent decomposition of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 are measured by using differential scanning calorimetry (DSC) and thermogravimetric (TGA) analyses in the temperature range from 25 to 700°C. Thermal analysis indicated that this DIL melted below 100°C and can, therefore, be classified as an ionic liquid. Vibrational spectroscopy studies were conducted by infrared (IR), Raman (FT-Raman) spectroscopy and DFT calculations. Moreover, the crystal structure is investigated by single crystal X-ray diffraction (XRD) method. The X-ray studies on [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2 show that it crystallizes in the monoclinic system with space group P21/c. The theoretical structural parameters such as bond lengths, bond angles and dihedral angles determined by DFT methods are in good agreement with the XRD results. [Display omitted] •Synthesis and crystal structure of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Thermal stability of [p‑C6H4(CH2ImMe)2+][(CF3SO2)2N−]2•Only the trans conformers of both cation and anion are present.•Interaction between [p‑C6H4(CH2ImMe)2] and [(CF3SO2)2N−]</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.molliq.2018.03.113</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-4839-7815</orcidid><orcidid>https://orcid.org/0000-0003-0932-0468</orcidid><orcidid>https://orcid.org/0000-0001-6339-4797</orcidid><orcidid>https://orcid.org/0000-0002-6266-3817</orcidid><orcidid>https://orcid.org/0000-0001-9198-9528</orcidid></addata></record>
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identifier ISSN: 0167-7322
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subjects Bis(trifluoromethanesulfonyl)imide
Chemical Sciences
Crystal structure
DFT
Di‑imidazolium
or physical chemistry
Organic chemistry
para‑Xylyl
Raman measurements
Theoretical and
Thermal stability
Vibrational spectra
title para‑Xylyl bis‑1‑methylimidazolium bis(trifluoromethanesulfonyl)imide: Synthesis, crystal structure, thermal stability, vibrational studies
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