Formation of solid solutions between racemic and enantiomeric citalopram oxalate
The X‐ray powder diffractograms of racemic citalopram oxalate and (S)‐citalopram oxalate are very similar, but the melting point of the racemate is higher than that of the pure enantiomer. The higher melting point indicates that the racemate is a racemic compound, rather than a conglomerate. The cry...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2011-05, Vol.23 (5), p.408-416 |
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| creator | de Diego, Heidi Lopez Bond, Andrew D. Dancer, Robert James |
| description | The X‐ray powder diffractograms of racemic citalopram oxalate and (S)‐citalopram oxalate are very similar, but the melting point of the racemate is higher than that of the pure enantiomer. The higher melting point indicates that the racemate is a racemic compound, rather than a conglomerate. The crystal structure of the enantiomer contains two molecules of (S)‐citalopram in the asymmetric unit. The conformation of the two molecules is different but they approximate mirror images of each other if the aromatic groups are interchanged. The crystal structure of the racemate is essentially isostructural with that of the enantiomer, having almost the same cell parameters but containing a crystallographic inversion centre that is not retained in the enantiomer structure. The closely‐comparable crystal structures permit solid solutions to be formed between racemic and enantiomeric citalopram oxalate. Phase diagrams of the (R)‐citalopram and (S)‐citalopram oxalate system are constructed, and they show that solid solutions are formed at all ratios of the two enantiomers. Chirality, 2011. © 2011 Wiley‐Liss, Inc. |
| doi_str_mv | 10.1002/chir.20943 |
| format | Article |
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The higher melting point indicates that the racemate is a racemic compound, rather than a conglomerate. The crystal structure of the enantiomer contains two molecules of (S)‐citalopram in the asymmetric unit. The conformation of the two molecules is different but they approximate mirror images of each other if the aromatic groups are interchanged. The crystal structure of the racemate is essentially isostructural with that of the enantiomer, having almost the same cell parameters but containing a crystallographic inversion centre that is not retained in the enantiomer structure. The closely‐comparable crystal structures permit solid solutions to be formed between racemic and enantiomeric citalopram oxalate. Phase diagrams of the (R)‐citalopram and (S)‐citalopram oxalate system are constructed, and they show that solid solutions are formed at all ratios of the two enantiomers. Chirality, 2011. © 2011 Wiley‐Liss, Inc.</description><identifier>ISSN: 0899-0042</identifier><identifier>ISSN: 1520-636X</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.20943</identifier><identifier>PMID: 21472783</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc., A Wiley Company</publisher><subject>Antidepressive Agents, Second-Generation - chemistry ; Approximation ; binary phase diagram ; Calorimetry, Differential Scanning ; Chirality ; citalopram ; Citalopram - chemistry ; Crystal structure ; disorder ; Enantiomers ; escitalopram oxalate ; isostructural ; Melting points ; Molecular Conformation ; Oxalates ; Oxalates - chemistry ; Phase diagrams ; racemic compound ; Solid solutions ; Solubility ; Solutions ; Stereoisomerism ; ternary phase diagram ; X-Ray Diffraction</subject><ispartof>Chirality (New York, N.Y.), 2011-05, Vol.23 (5), p.408-416</ispartof><rights>Copyright © 2011 Wiley‐Liss, Inc.</rights><rights>Copyright © 2011 Wiley-Liss, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4323-f6fe48eb2d908d635eee421b82dccc7c6c151c61de73737eba798a276cb3aa5c3</citedby><cites>FETCH-LOGICAL-c4323-f6fe48eb2d908d635eee421b82dccc7c6c151c61de73737eba798a276cb3aa5c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.20943$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.20943$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21472783$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>de Diego, Heidi Lopez</creatorcontrib><creatorcontrib>Bond, Andrew D.</creatorcontrib><creatorcontrib>Dancer, Robert James</creatorcontrib><title>Formation of solid solutions between racemic and enantiomeric citalopram oxalate</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>The X‐ray powder diffractograms of racemic citalopram oxalate and (S)‐citalopram oxalate are very similar, but the melting point of the racemate is higher than that of the pure enantiomer. The higher melting point indicates that the racemate is a racemic compound, rather than a conglomerate. The crystal structure of the enantiomer contains two molecules of (S)‐citalopram in the asymmetric unit. The conformation of the two molecules is different but they approximate mirror images of each other if the aromatic groups are interchanged. The crystal structure of the racemate is essentially isostructural with that of the enantiomer, having almost the same cell parameters but containing a crystallographic inversion centre that is not retained in the enantiomer structure. The closely‐comparable crystal structures permit solid solutions to be formed between racemic and enantiomeric citalopram oxalate. Phase diagrams of the (R)‐citalopram and (S)‐citalopram oxalate system are constructed, and they show that solid solutions are formed at all ratios of the two enantiomers. Chirality, 2011. © 2011 Wiley‐Liss, Inc.</description><subject>Antidepressive Agents, Second-Generation - chemistry</subject><subject>Approximation</subject><subject>binary phase diagram</subject><subject>Calorimetry, Differential Scanning</subject><subject>Chirality</subject><subject>citalopram</subject><subject>Citalopram - chemistry</subject><subject>Crystal structure</subject><subject>disorder</subject><subject>Enantiomers</subject><subject>escitalopram oxalate</subject><subject>isostructural</subject><subject>Melting points</subject><subject>Molecular Conformation</subject><subject>Oxalates</subject><subject>Oxalates - chemistry</subject><subject>Phase diagrams</subject><subject>racemic compound</subject><subject>Solid solutions</subject><subject>Solubility</subject><subject>Solutions</subject><subject>Stereoisomerism</subject><subject>ternary phase diagram</subject><subject>X-Ray Diffraction</subject><issn>0899-0042</issn><issn>1520-636X</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU1Lw0AQhhdRtFYv_gDJTRGi-53kKMVaQfyiordls5ngapKtuym2_96tVY8iAzMw88wLMy9CBwSfEozpmXmx_pTigrMNNCCC4lQy-byJBjgvihRjTnfQbgivGONCMr6NdijhGc1yNkB3Y-db3VvXJa5OgmtstcrzVSckJfQfAF3itYHWmkR3VQKd7uK0BR8bxva6cTOv28QtdKN72ENbtW4C7H_XIXocX0xHk_T69vJqdH6dGs4oS2tZA8-hpFWB80oyAQCckjKnlTEmM9IQQYwkFWQsBpQ6K3JNM2lKprUwbIiO1roz797nEHrV2mCgaXQHbh5ULmm8XFIRyeM_SZJxLnNRiH-iGRfxdUN0skaNdyF4qNXM21b7pSJYrWxRK1vUly0RPvzWnZctVL_ojw8RIGvgwzaw_ENKjSZXDz-i6XrHhh4WvzvavykZXybU082lonfTcTG9EeqefQJ6c6eg</recordid><startdate>201105</startdate><enddate>201105</enddate><creator>de Diego, Heidi Lopez</creator><creator>Bond, Andrew D.</creator><creator>Dancer, Robert James</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><scope>BSCLL</scope><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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201105</creationdate><title>Formation of solid solutions between racemic and enantiomeric citalopram oxalate</title><author>de Diego, Heidi Lopez ; Bond, Andrew D. ; Dancer, Robert James</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4323-f6fe48eb2d908d635eee421b82dccc7c6c151c61de73737eba798a276cb3aa5c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Antidepressive Agents, Second-Generation - chemistry</topic><topic>Approximation</topic><topic>binary phase diagram</topic><topic>Calorimetry, Differential Scanning</topic><topic>Chirality</topic><topic>citalopram</topic><topic>Citalopram - chemistry</topic><topic>Crystal structure</topic><topic>disorder</topic><topic>Enantiomers</topic><topic>escitalopram oxalate</topic><topic>isostructural</topic><topic>Melting points</topic><topic>Molecular Conformation</topic><topic>Oxalates</topic><topic>Oxalates - chemistry</topic><topic>Phase diagrams</topic><topic>racemic compound</topic><topic>Solid solutions</topic><topic>Solubility</topic><topic>Solutions</topic><topic>Stereoisomerism</topic><topic>ternary phase diagram</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>de Diego, Heidi Lopez</creatorcontrib><creatorcontrib>Bond, Andrew D.</creatorcontrib><creatorcontrib>Dancer, Robert James</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</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>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>de Diego, Heidi Lopez</au><au>Bond, Andrew D.</au><au>Dancer, Robert James</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation of solid solutions between racemic and enantiomeric citalopram oxalate</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2011-05</date><risdate>2011</risdate><volume>23</volume><issue>5</issue><spage>408</spage><epage>416</epage><pages>408-416</pages><issn>0899-0042</issn><issn>1520-636X</issn><eissn>1520-636X</eissn><abstract>The X‐ray powder diffractograms of racemic citalopram oxalate and (S)‐citalopram oxalate are very similar, but the melting point of the racemate is higher than that of the pure enantiomer. The higher melting point indicates that the racemate is a racemic compound, rather than a conglomerate. The crystal structure of the enantiomer contains two molecules of (S)‐citalopram in the asymmetric unit. The conformation of the two molecules is different but they approximate mirror images of each other if the aromatic groups are interchanged. The crystal structure of the racemate is essentially isostructural with that of the enantiomer, having almost the same cell parameters but containing a crystallographic inversion centre that is not retained in the enantiomer structure. The closely‐comparable crystal structures permit solid solutions to be formed between racemic and enantiomeric citalopram oxalate. Phase diagrams of the (R)‐citalopram and (S)‐citalopram oxalate system are constructed, and they show that solid solutions are formed at all ratios of the two enantiomers. 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| subjects | Antidepressive Agents, Second-Generation - chemistry Approximation binary phase diagram Calorimetry, Differential Scanning Chirality citalopram Citalopram - chemistry Crystal structure disorder Enantiomers escitalopram oxalate isostructural Melting points Molecular Conformation Oxalates Oxalates - chemistry Phase diagrams racemic compound Solid solutions Solubility Solutions Stereoisomerism ternary phase diagram X-Ray Diffraction |
| title | Formation of solid solutions between racemic and enantiomeric citalopram oxalate |
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