Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate
A distortion of the aromatic character and stabilization of the imino-form as a result of the protonation of 4-dimethylaminopyridine was established by IR-, UV- and 1H NMR-spectral analysis of 4-diaminopyridinium hydrogensquarate. Quantum chemical calculations were carried out at MP2 and B3LYP level...
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| Veröffentlicht in: | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2008-11, Vol.71 (2), p.695-702 |
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| container_title | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy |
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| creator | Koleva, Bojidarka B. Kolev, Tsonko Seidel, Rüdiger W. Tsanev, Tsanko Mayer-Figge, Heike Spiteller, Michael Sheldrick, William S. |
| description | A distortion of the aromatic character and stabilization of the imino-form as a result of the protonation of 4-dimethylaminopyridine was established by IR-, UV- and
1H NMR-spectral analysis of 4-diaminopyridinium hydrogensquarate. Quantum chemical calculations were carried out at MP2 and B3LYP levels of theory and a 6-311++G** basis set with a view to determining the changes in geometrical parameters and IR-spectroscopic characteristics resulting from N
py protonation. Linear-dichroic IR-spectroscopy coupled with the orientation techniques of solid samples as liquid crystal suspensions and melted solid polycrystalline films was applied for the identification of the IR-bands, characteristic for the structural fragments of the neutral and imino-form of the pyridine derivative. The spectral results were compared with the structure, obtained by a single crystal X-ray analysis. The salt contains dimmers of hydrogensquarate anions and N
py protonated cations of which the former are stabilized by strong intermolecular OH…O interactions (2.552
Å and 143.1(2)°). The 4-diaminopyridinium cation interacts with the anion through moderate NH…O bonds (2.729
Å and 165.0(0)°). Individual cations are π–π stacked with their neighbors at a distance of 3.406
Å. |
| doi_str_mv | 10.1016/j.saa.2008.01.033 |
| format | Article |
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1H NMR-spectral analysis of 4-diaminopyridinium hydrogensquarate. Quantum chemical calculations were carried out at MP2 and B3LYP levels of theory and a 6-311++G** basis set with a view to determining the changes in geometrical parameters and IR-spectroscopic characteristics resulting from N
py protonation. Linear-dichroic IR-spectroscopy coupled with the orientation techniques of solid samples as liquid crystal suspensions and melted solid polycrystalline films was applied for the identification of the IR-bands, characteristic for the structural fragments of the neutral and imino-form of the pyridine derivative. The spectral results were compared with the structure, obtained by a single crystal X-ray analysis. The salt contains dimmers of hydrogensquarate anions and N
py protonated cations of which the former are stabilized by strong intermolecular OH…O interactions (2.552
Å and 143.1(2)°). The 4-diaminopyridinium cation interacts with the anion through moderate NH…O bonds (2.729
Å and 165.0(0)°). Individual cations are π–π stacked with their neighbors at a distance of 3.406
Å.</description><identifier>ISSN: 1386-1425</identifier><identifier>DOI: 10.1016/j.saa.2008.01.033</identifier><identifier>PMID: 18343192</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>4-Aminopyridine - analogs & derivatives ; 4-Aminopyridine - chemistry ; 4-Dimethylaminopyridinium hydrogensquarate ; Crystal structure ; Crystallization ; Cyclobutanes - chemistry ; Hydrogen - chemistry ; Hydrogen Bonding ; Models, Molecular ; Molecular Structure ; Quantum chemical calculations ; Solid-state IR-LD analysis ; Spectrophotometry ; UV- and 1H NMR data ; Vibration</subject><ispartof>Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 2008-11, Vol.71 (2), p.695-702</ispartof><rights>2008 Elsevier B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c351t-8c2e453d730f4590c4c8545b9966d426060118522ed42226cf4505ee09fb151c3</citedby><cites>FETCH-LOGICAL-c351t-8c2e453d730f4590c4c8545b9966d426060118522ed42226cf4505ee09fb151c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.saa.2008.01.033$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18343192$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Koleva, Bojidarka B.</creatorcontrib><creatorcontrib>Kolev, Tsonko</creatorcontrib><creatorcontrib>Seidel, Rüdiger W.</creatorcontrib><creatorcontrib>Tsanev, Tsanko</creatorcontrib><creatorcontrib>Mayer-Figge, Heike</creatorcontrib><creatorcontrib>Spiteller, Michael</creatorcontrib><creatorcontrib>Sheldrick, William S.</creatorcontrib><title>Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate</title><title>Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy</title><addtitle>Spectrochim Acta A Mol Biomol Spectrosc</addtitle><description>A distortion of the aromatic character and stabilization of the imino-form as a result of the protonation of 4-dimethylaminopyridine was established by IR-, UV- and
1H NMR-spectral analysis of 4-diaminopyridinium hydrogensquarate. Quantum chemical calculations were carried out at MP2 and B3LYP levels of theory and a 6-311++G** basis set with a view to determining the changes in geometrical parameters and IR-spectroscopic characteristics resulting from N
py protonation. Linear-dichroic IR-spectroscopy coupled with the orientation techniques of solid samples as liquid crystal suspensions and melted solid polycrystalline films was applied for the identification of the IR-bands, characteristic for the structural fragments of the neutral and imino-form of the pyridine derivative. The spectral results were compared with the structure, obtained by a single crystal X-ray analysis. The salt contains dimmers of hydrogensquarate anions and N
py protonated cations of which the former are stabilized by strong intermolecular OH…O interactions (2.552
Å and 143.1(2)°). The 4-diaminopyridinium cation interacts with the anion through moderate NH…O bonds (2.729
Å and 165.0(0)°). Individual cations are π–π stacked with their neighbors at a distance of 3.406
Å.</description><subject>4-Aminopyridine - analogs & derivatives</subject><subject>4-Aminopyridine - chemistry</subject><subject>4-Dimethylaminopyridinium hydrogensquarate</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Cyclobutanes - chemistry</subject><subject>Hydrogen - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Quantum chemical calculations</subject><subject>Solid-state IR-LD analysis</subject><subject>Spectrophotometry</subject><subject>UV- and 1H NMR data</subject><subject>Vibration</subject><issn>1386-1425</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEFr3DAQhXVIyW43-QG5FJ96szMjWY5NTyW0TSDQQ5tbQGilcaLFtrySXNh_HyW7kFtPw8D3HryPsSuECgGb610Vta44QFsBViDEGVujaJsSay5X7HOMOwDAlsM5W2EraoEdX7OnPzOZFHw0fnam0JMtYgqLSUvQQ0HDYpzVyfmp8H1Rl9aNlF4Ogx7d5OdDcNZN9J5yKRYvBxv8M01xv-igE12wT70eIl2e7oY9_vzx9_aufPj96_72-0NphMRUtoZTLYW9EdDXsgNTm1bWctt1TWNr3kADiK3knPLHeWMyBZIIun6LEo3YsK_H3jn4_UIxqdFFQ8OgJ_JLVE13w_NymUE8giYvjoF6NQc36nBQCOpNo9qprFG9aVSAKmvMmS-n8mU7kv1InBxm4NsRoDzxn6OgonE0GbIuZLfKevef-lc_BoWK</recordid><startdate>20081115</startdate><enddate>20081115</enddate><creator>Koleva, Bojidarka B.</creator><creator>Kolev, Tsonko</creator><creator>Seidel, Rüdiger W.</creator><creator>Tsanev, Tsanko</creator><creator>Mayer-Figge, Heike</creator><creator>Spiteller, Michael</creator><creator>Sheldrick, William S.</creator><general>Elsevier B.V</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20081115</creationdate><title>Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate</title><author>Koleva, Bojidarka B. ; Kolev, Tsonko ; Seidel, Rüdiger W. ; Tsanev, Tsanko ; Mayer-Figge, Heike ; Spiteller, Michael ; Sheldrick, William S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-8c2e453d730f4590c4c8545b9966d426060118522ed42226cf4505ee09fb151c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>4-Aminopyridine - analogs & derivatives</topic><topic>4-Aminopyridine - chemistry</topic><topic>4-Dimethylaminopyridinium hydrogensquarate</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Cyclobutanes - chemistry</topic><topic>Hydrogen - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Quantum chemical calculations</topic><topic>Solid-state IR-LD analysis</topic><topic>Spectrophotometry</topic><topic>UV- and 1H NMR data</topic><topic>Vibration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Koleva, Bojidarka B.</creatorcontrib><creatorcontrib>Kolev, Tsonko</creatorcontrib><creatorcontrib>Seidel, Rüdiger W.</creatorcontrib><creatorcontrib>Tsanev, Tsanko</creatorcontrib><creatorcontrib>Mayer-Figge, Heike</creatorcontrib><creatorcontrib>Spiteller, Michael</creatorcontrib><creatorcontrib>Sheldrick, William S.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Koleva, Bojidarka B.</au><au>Kolev, Tsonko</au><au>Seidel, Rüdiger W.</au><au>Tsanev, Tsanko</au><au>Mayer-Figge, Heike</au><au>Spiteller, Michael</au><au>Sheldrick, William S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate</atitle><jtitle>Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy</jtitle><addtitle>Spectrochim Acta A Mol Biomol Spectrosc</addtitle><date>2008-11-15</date><risdate>2008</risdate><volume>71</volume><issue>2</issue><spage>695</spage><epage>702</epage><pages>695-702</pages><issn>1386-1425</issn><abstract>A distortion of the aromatic character and stabilization of the imino-form as a result of the protonation of 4-dimethylaminopyridine was established by IR-, UV- and
1H NMR-spectral analysis of 4-diaminopyridinium hydrogensquarate. Quantum chemical calculations were carried out at MP2 and B3LYP levels of theory and a 6-311++G** basis set with a view to determining the changes in geometrical parameters and IR-spectroscopic characteristics resulting from N
py protonation. Linear-dichroic IR-spectroscopy coupled with the orientation techniques of solid samples as liquid crystal suspensions and melted solid polycrystalline films was applied for the identification of the IR-bands, characteristic for the structural fragments of the neutral and imino-form of the pyridine derivative. The spectral results were compared with the structure, obtained by a single crystal X-ray analysis. The salt contains dimmers of hydrogensquarate anions and N
py protonated cations of which the former are stabilized by strong intermolecular OH…O interactions (2.552
Å and 143.1(2)°). The 4-diaminopyridinium cation interacts with the anion through moderate NH…O bonds (2.729
Å and 165.0(0)°). Individual cations are π–π stacked with their neighbors at a distance of 3.406
Å.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>18343192</pmid><doi>10.1016/j.saa.2008.01.033</doi><tpages>8</tpages></addata></record> |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 4-Aminopyridine - analogs & derivatives 4-Aminopyridine - chemistry 4-Dimethylaminopyridinium hydrogensquarate Crystal structure Crystallization Cyclobutanes - chemistry Hydrogen - chemistry Hydrogen Bonding Models, Molecular Molecular Structure Quantum chemical calculations Solid-state IR-LD analysis Spectrophotometry UV- and 1H NMR data Vibration |
| title | Spectroscopic and structural elucidation of 4-dimethylaminopyridine and its hydrogensquarate |
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