Synthesis and crystal structures of N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N -iso-propyl-idene- N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate
Two 2,4,6-tri-methyl-aniline-based trifuloro-methane-sulfonate (tri-fluoro-methane-sulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction. ,2,4,6-Tetra-methyl-anilinium tri-fluoro-methane-sulfonate, [C H NH ][CF O S ] ( ), was synthesized methyl-ation of 2,4,6-tri-me...
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| Veröffentlicht in: | Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2024-04, Vol.80 (Pt 5), p.543-549 |
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| creator | Stewart, John W Irons, Elena M Osorio Abanto, Giovanna Zeller, Matthias Zaleski, Curtis M Predecki, Daniel P |
| description | Two 2,4,6-tri-methyl-aniline-based trifuloro-methane-sulfonate (tri-fluoro-methane-sulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction.
,2,4,6-Tetra-methyl-anilinium tri-fluoro-methane-sulfonate, [C
H
NH
][CF
O
S
] (
), was synthesized
methyl-ation of 2,4,6-tri-methyl-aniline.
-Iso-propyl-idene-
,2,4,6-tetra-methyl-anilinium tri-fluoro-meth-ane-sulfonate, [C
H
N
][CF
O
S
] (
), was synthesized in a two-step reaction where the imine,
-iso-propyl-idene-2,4,6-tri-methyl-aniline, was first prepared
a dehydration reaction to form the Schiff base, followed by methyl-ation using methyl tri-fluoro-methane-sulfonate to form the iminium ion. In compound
, both hydrogen bonding and π-π inter-actions form the main inter-molecular inter-actions. The primary inter-action is a strong N-H⋯O hydrogen bond with the oxygen atoms of the tri-fluoro-methane-sulfonate anions bonded to the hydrogen atoms of the ammonium nitro-gen atom to generate a one-dimensional chain. The [C
H
NH
] cations form dimers where the benzene rings form a π-π inter-action with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129 (8) Å, and the inter-planar spacing and ring slippage between the dimers are 3.5156 (5) and 1.718 Å, respectively. For
, the [C
H
N
] cations also form dimers as in
, but with the benzene rings highly slipped. The distance between the calculated centroids of the benzene rings is 4.8937 (8) Å, and inter-planar spacing and ring slippage are 3.3646 (5) and 3.553 Å, respectively. The major inter-molecular inter-actions in
are instead a series of weaker C-H⋯O hydrogen bonds [C⋯O distances of 3.1723 (17), 3.3789 (18), and 3.3789 (18) Å], an inter-action virtually absent in the structure of
. Fluorine atoms are not involved in strong directional inter-actions in either structure. |
| doi_str_mv | 10.1107/S2056989024003438 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_11074574</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3053136799</sourcerecordid><originalsourceid>FETCH-LOGICAL-p1124-f8261ce8ac8767f0f75442e52770289d067e28c1983da34367ae64e170f2895d3</originalsourceid><addsrcrecordid>eNqlkctOxSAQhonRqFEfwI3p0sVBuRXoyhjjLTG6UNcNtlMPhpYK1OS8mM8n53iJrl1B5v_5_hkGoX1Kjigl6viekVJWuiJMEMIF12toe1nCy9r6r_sW2ovxhRBCRcllyTbRFteKUUHlNnq_XwxpDtHGwgxt0YRFTMYVMYWpSVOAWPiuuC1mbCZmEidIweAe0nzhsBmss4Od-iIFizs3-eBXmhkAx8l1fjAJVtjbAtvo8Rj8mB_aFrLjX9RdtNEZF2Hv69xBjxfnD2dX-Obu8vrs9AaPlDKBO80kbUCbRiupOtKpUggGJVOKMF21RCpguqGV5q3JfyiVASmAKtJluWz5Djr55I7TUw9tA0Nu1dVjsL0Ji9obW_9VBjuvn_1bvVyRKJXIhMMvQvCvE8RU9zY24Fyex0-x5qTkNAdXVbYe_A77SfneFv8A1reaaQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3053136799</pqid></control><display><type>article</type><title>Synthesis and crystal structures of N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N -iso-propyl-idene- N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate</title><source>DOAJ Directory of Open Access Journals</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><source>PubMed Central Open Access</source><creator>Stewart, John W ; Irons, Elena M ; Osorio Abanto, Giovanna ; Zeller, Matthias ; Zaleski, Curtis M ; Predecki, Daniel P</creator><creatorcontrib>Stewart, John W ; Irons, Elena M ; Osorio Abanto, Giovanna ; Zeller, Matthias ; Zaleski, Curtis M ; Predecki, Daniel P</creatorcontrib><description>Two 2,4,6-tri-methyl-aniline-based trifuloro-methane-sulfonate (tri-fluoro-methane-sulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction.
,2,4,6-Tetra-methyl-anilinium tri-fluoro-methane-sulfonate, [C
H
NH
][CF
O
S
] (
), was synthesized
methyl-ation of 2,4,6-tri-methyl-aniline.
-Iso-propyl-idene-
,2,4,6-tetra-methyl-anilinium tri-fluoro-meth-ane-sulfonate, [C
H
N
][CF
O
S
] (
), was synthesized in a two-step reaction where the imine,
-iso-propyl-idene-2,4,6-tri-methyl-aniline, was first prepared
a dehydration reaction to form the Schiff base, followed by methyl-ation using methyl tri-fluoro-methane-sulfonate to form the iminium ion. In compound
, both hydrogen bonding and π-π inter-actions form the main inter-molecular inter-actions. The primary inter-action is a strong N-H⋯O hydrogen bond with the oxygen atoms of the tri-fluoro-methane-sulfonate anions bonded to the hydrogen atoms of the ammonium nitro-gen atom to generate a one-dimensional chain. The [C
H
NH
] cations form dimers where the benzene rings form a π-π inter-action with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129 (8) Å, and the inter-planar spacing and ring slippage between the dimers are 3.5156 (5) and 1.718 Å, respectively. For
, the [C
H
N
] cations also form dimers as in
, but with the benzene rings highly slipped. The distance between the calculated centroids of the benzene rings is 4.8937 (8) Å, and inter-planar spacing and ring slippage are 3.3646 (5) and 3.553 Å, respectively. The major inter-molecular inter-actions in
are instead a series of weaker C-H⋯O hydrogen bonds [C⋯O distances of 3.1723 (17), 3.3789 (18), and 3.3789 (18) Å], an inter-action virtually absent in the structure of
. Fluorine atoms are not involved in strong directional inter-actions in either structure.</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989024003438</identifier><identifier>PMID: 38721416</identifier><language>eng</language><publisher>England: International Union of Crystallography</publisher><subject>Research Communications</subject><ispartof>Acta crystallographica. Section E, Crystallographic communications, 2024-04, Vol.80 (Pt 5), p.543-549</ispartof><rights>Stewart et al. 2024.</rights><rights>Stewart et al. 2024 2024</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-7911-8559 ; 0000-0003-4831-2911 ; 0009-0001-3323-444X ; 0000-0002-3305-852X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11074574/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11074574/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38721416$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Stewart, John W</creatorcontrib><creatorcontrib>Irons, Elena M</creatorcontrib><creatorcontrib>Osorio Abanto, Giovanna</creatorcontrib><creatorcontrib>Zeller, Matthias</creatorcontrib><creatorcontrib>Zaleski, Curtis M</creatorcontrib><creatorcontrib>Predecki, Daniel P</creatorcontrib><title>Synthesis and crystal structures of N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N -iso-propyl-idene- N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate</title><title>Acta crystallographica. Section E, Crystallographic communications</title><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><description>Two 2,4,6-tri-methyl-aniline-based trifuloro-methane-sulfonate (tri-fluoro-methane-sulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction.
,2,4,6-Tetra-methyl-anilinium tri-fluoro-methane-sulfonate, [C
H
NH
][CF
O
S
] (
), was synthesized
methyl-ation of 2,4,6-tri-methyl-aniline.
-Iso-propyl-idene-
,2,4,6-tetra-methyl-anilinium tri-fluoro-meth-ane-sulfonate, [C
H
N
][CF
O
S
] (
), was synthesized in a two-step reaction where the imine,
-iso-propyl-idene-2,4,6-tri-methyl-aniline, was first prepared
a dehydration reaction to form the Schiff base, followed by methyl-ation using methyl tri-fluoro-methane-sulfonate to form the iminium ion. In compound
, both hydrogen bonding and π-π inter-actions form the main inter-molecular inter-actions. The primary inter-action is a strong N-H⋯O hydrogen bond with the oxygen atoms of the tri-fluoro-methane-sulfonate anions bonded to the hydrogen atoms of the ammonium nitro-gen atom to generate a one-dimensional chain. The [C
H
NH
] cations form dimers where the benzene rings form a π-π inter-action with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129 (8) Å, and the inter-planar spacing and ring slippage between the dimers are 3.5156 (5) and 1.718 Å, respectively. For
, the [C
H
N
] cations also form dimers as in
, but with the benzene rings highly slipped. The distance between the calculated centroids of the benzene rings is 4.8937 (8) Å, and inter-planar spacing and ring slippage are 3.3646 (5) and 3.553 Å, respectively. The major inter-molecular inter-actions in
are instead a series of weaker C-H⋯O hydrogen bonds [C⋯O distances of 3.1723 (17), 3.3789 (18), and 3.3789 (18) Å], an inter-action virtually absent in the structure of
. Fluorine atoms are not involved in strong directional inter-actions in either structure.</description><subject>Research Communications</subject><issn>2056-9890</issn><issn>2056-9890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqlkctOxSAQhonRqFEfwI3p0sVBuRXoyhjjLTG6UNcNtlMPhpYK1OS8mM8n53iJrl1B5v_5_hkGoX1Kjigl6viekVJWuiJMEMIF12toe1nCy9r6r_sW2ovxhRBCRcllyTbRFteKUUHlNnq_XwxpDtHGwgxt0YRFTMYVMYWpSVOAWPiuuC1mbCZmEidIweAe0nzhsBmss4Od-iIFizs3-eBXmhkAx8l1fjAJVtjbAtvo8Rj8mB_aFrLjX9RdtNEZF2Hv69xBjxfnD2dX-Obu8vrs9AaPlDKBO80kbUCbRiupOtKpUggGJVOKMF21RCpguqGV5q3JfyiVASmAKtJluWz5Djr55I7TUw9tA0Nu1dVjsL0Ji9obW_9VBjuvn_1bvVyRKJXIhMMvQvCvE8RU9zY24Fyex0-x5qTkNAdXVbYe_A77SfneFv8A1reaaQ</recordid><startdate>20240401</startdate><enddate>20240401</enddate><creator>Stewart, John W</creator><creator>Irons, Elena M</creator><creator>Osorio Abanto, Giovanna</creator><creator>Zeller, Matthias</creator><creator>Zaleski, Curtis M</creator><creator>Predecki, Daniel P</creator><general>International Union of Crystallography</general><scope>NPM</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-7911-8559</orcidid><orcidid>https://orcid.org/0000-0003-4831-2911</orcidid><orcidid>https://orcid.org/0009-0001-3323-444X</orcidid><orcidid>https://orcid.org/0000-0002-3305-852X</orcidid></search><sort><creationdate>20240401</creationdate><title>Synthesis and crystal structures of N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N -iso-propyl-idene- N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate</title><author>Stewart, John W ; Irons, Elena M ; Osorio Abanto, Giovanna ; Zeller, Matthias ; Zaleski, Curtis M ; Predecki, Daniel P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p1124-f8261ce8ac8767f0f75442e52770289d067e28c1983da34367ae64e170f2895d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Research Communications</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stewart, John W</creatorcontrib><creatorcontrib>Irons, Elena M</creatorcontrib><creatorcontrib>Osorio Abanto, Giovanna</creatorcontrib><creatorcontrib>Zeller, Matthias</creatorcontrib><creatorcontrib>Zaleski, Curtis M</creatorcontrib><creatorcontrib>Predecki, Daniel P</creatorcontrib><collection>PubMed</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stewart, John W</au><au>Irons, Elena M</au><au>Osorio Abanto, Giovanna</au><au>Zeller, Matthias</au><au>Zaleski, Curtis M</au><au>Predecki, Daniel P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and crystal structures of N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N -iso-propyl-idene- N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate</atitle><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><date>2024-04-01</date><risdate>2024</risdate><volume>80</volume><issue>Pt 5</issue><spage>543</spage><epage>549</epage><pages>543-549</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>Two 2,4,6-tri-methyl-aniline-based trifuloro-methane-sulfonate (tri-fluoro-methane-sulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction.
,2,4,6-Tetra-methyl-anilinium tri-fluoro-methane-sulfonate, [C
H
NH
][CF
O
S
] (
), was synthesized
methyl-ation of 2,4,6-tri-methyl-aniline.
-Iso-propyl-idene-
,2,4,6-tetra-methyl-anilinium tri-fluoro-meth-ane-sulfonate, [C
H
N
][CF
O
S
] (
), was synthesized in a two-step reaction where the imine,
-iso-propyl-idene-2,4,6-tri-methyl-aniline, was first prepared
a dehydration reaction to form the Schiff base, followed by methyl-ation using methyl tri-fluoro-methane-sulfonate to form the iminium ion. In compound
, both hydrogen bonding and π-π inter-actions form the main inter-molecular inter-actions. The primary inter-action is a strong N-H⋯O hydrogen bond with the oxygen atoms of the tri-fluoro-methane-sulfonate anions bonded to the hydrogen atoms of the ammonium nitro-gen atom to generate a one-dimensional chain. The [C
H
NH
] cations form dimers where the benzene rings form a π-π inter-action with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129 (8) Å, and the inter-planar spacing and ring slippage between the dimers are 3.5156 (5) and 1.718 Å, respectively. For
, the [C
H
N
] cations also form dimers as in
, but with the benzene rings highly slipped. The distance between the calculated centroids of the benzene rings is 4.8937 (8) Å, and inter-planar spacing and ring slippage are 3.3646 (5) and 3.553 Å, respectively. The major inter-molecular inter-actions in
are instead a series of weaker C-H⋯O hydrogen bonds [C⋯O distances of 3.1723 (17), 3.3789 (18), and 3.3789 (18) Å], an inter-action virtually absent in the structure of
. Fluorine atoms are not involved in strong directional inter-actions in either structure.</abstract><cop>England</cop><pub>International Union of Crystallography</pub><pmid>38721416</pmid><doi>10.1107/S2056989024003438</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-7911-8559</orcidid><orcidid>https://orcid.org/0000-0003-4831-2911</orcidid><orcidid>https://orcid.org/0009-0001-3323-444X</orcidid><orcidid>https://orcid.org/0000-0002-3305-852X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Research Communications |
| title | Synthesis and crystal structures of N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate and N -iso-propyl-idene- N ,2,4,6-tetra-methyl-anilinium tri-fluoro-methane-sulfonate |
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