A comparative study on the dynamics of epimeric 1-hydroxymethylquinolizidines: I. Conformational analysis of monomers and spectroscopic data for solid state, liquid state, and dilute solutions
A systematic comparative study of the conformational dynamics of lupinine and epilupinine, two 1-hydroxymethyl quinolizidine epimers, as a function of phase transition and of their protonation is presented. Lupinine and epilupinine have a trans-quinolizidine configuration and they differ only in the...
Gespeichert in:
| Veröffentlicht in: | Canadian journal of chemistry 1987-01, Vol.65 (1), p.205-212 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 212 |
|---|---|
| container_issue | 1 |
| container_start_page | 205 |
| container_title | Canadian journal of chemistry |
| container_volume | 65 |
| creator | KULINSKA, K WIEWIOROWSKI, M |
| description | A systematic comparative study of the conformational dynamics of lupinine and epilupinine, two 1-hydroxymethyl quinolizidine epimers, as a function of phase transition and of their protonation is presented. Lupinine and epilupinine have a trans-quinolizidine configuration and they differ only in the position of the CH
2
OH group. The axial position of this group allows the formation of an intramolecular hydrogen bond OH ... N in lupinine, in contrast to epilupinine in which this group is in the equatorial position. Intrinsic conformational equilibria for both epimers have been defined. Despite the significant difference in the population of the preferred rotamers of lupinine and epilupinine, both epimers adopt very similar crystal structures, but in all other states and forms, e.g., pure liquids, solutions in inert and polar solvents, and protonated salts, they behave in drastically different ways. |
| doi_str_mv | 10.1139/v87-033 |
| format | Article |
| fullrecord | <record><control><sourceid>pascalfrancis_nrcre</sourceid><recordid>TN_cdi_nrcresearch_primary_10_1139_v87_033</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>8346588</sourcerecordid><originalsourceid>FETCH-LOGICAL-c233t-a92701c7c1a559cd745d203607cf758c40e99b9a75d917e8370ee226308632783</originalsourceid><addsrcrecordid>eNp9kM9O3DAQh62qSN0C4hV8qIpUEeo_ydrhhlaFIiH1Us7RYE-0rhI7tb2I8HQ8Wh0WcSsXWzP-5hvrR8gJZ-ecy_b7g1YVk_IDWfFas0qKln8kK8aYrmpWi0_kc0p_SqmYaFbk-ZKaME4QIbsHpCnv7EyDp3mL1M4eRmcSDT3FyY0YnaG82s42hsd5xLydh78758Pgnpx1HtMFvTmnm-D7EMciDB4GCuWYk3uxjMGHokmlaWma0OQYkglT8VrIQMscTUVXHjNkPKODKwveqmXKumGXcaF2y4J0RA56GBIev96H5O7qx-_Nz-r21_XN5vK2MkLKXEErFONGGQ5N0xqr6sYKJtdMmV412tQM2_a-BdXYlivUUjFEIdaS6bUUSstDcrr3mvLlFLHvpuhGiHPHWbcE35XguxJ8Ib_syQmSgaGP4I1Lb7iW9brRi_DbHvPRREwI0WzfcX79P_wKdZPt5T-XG6Jx</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A comparative study on the dynamics of epimeric 1-hydroxymethylquinolizidines: I. Conformational analysis of monomers and spectroscopic data for solid state, liquid state, and dilute solutions</title><source>NRC Research Press</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>KULINSKA, K ; WIEWIOROWSKI, M</creator><creatorcontrib>KULINSKA, K ; WIEWIOROWSKI, M</creatorcontrib><description>A systematic comparative study of the conformational dynamics of lupinine and epilupinine, two 1-hydroxymethyl quinolizidine epimers, as a function of phase transition and of their protonation is presented. Lupinine and epilupinine have a trans-quinolizidine configuration and they differ only in the position of the CH
2
OH group. The axial position of this group allows the formation of an intramolecular hydrogen bond OH ... N in lupinine, in contrast to epilupinine in which this group is in the equatorial position. Intrinsic conformational equilibria for both epimers have been defined. Despite the significant difference in the population of the preferred rotamers of lupinine and epilupinine, both epimers adopt very similar crystal structures, but in all other states and forms, e.g., pure liquids, solutions in inert and polar solvents, and protonated salts, they behave in drastically different ways.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v87-033</identifier><identifier>CODEN: CJCHAG</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><subject>Atomic and molecular physics ; Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics) ; Exact sciences and technology ; Molecular properties and interactions with photons ; Physics ; Properties of molecules and molecular ions</subject><ispartof>Canadian journal of chemistry, 1987-01, Vol.65 (1), p.205-212</ispartof><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c233t-a92701c7c1a559cd745d203607cf758c40e99b9a75d917e8370ee226308632783</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v87-033$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v87-033$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,776,780,2919,4010,27900,27901,27902,64401,65207</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8346588$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>KULINSKA, K</creatorcontrib><creatorcontrib>WIEWIOROWSKI, M</creatorcontrib><title>A comparative study on the dynamics of epimeric 1-hydroxymethylquinolizidines: I. Conformational analysis of monomers and spectroscopic data for solid state, liquid state, and dilute solutions</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>A systematic comparative study of the conformational dynamics of lupinine and epilupinine, two 1-hydroxymethyl quinolizidine epimers, as a function of phase transition and of their protonation is presented. Lupinine and epilupinine have a trans-quinolizidine configuration and they differ only in the position of the CH
2
OH group. The axial position of this group allows the formation of an intramolecular hydrogen bond OH ... N in lupinine, in contrast to epilupinine in which this group is in the equatorial position. Intrinsic conformational equilibria for both epimers have been defined. Despite the significant difference in the population of the preferred rotamers of lupinine and epilupinine, both epimers adopt very similar crystal structures, but in all other states and forms, e.g., pure liquids, solutions in inert and polar solvents, and protonated salts, they behave in drastically different ways.</description><subject>Atomic and molecular physics</subject><subject>Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics)</subject><subject>Exact sciences and technology</subject><subject>Molecular properties and interactions with photons</subject><subject>Physics</subject><subject>Properties of molecules and molecular ions</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNp9kM9O3DAQh62qSN0C4hV8qIpUEeo_ydrhhlaFIiH1Us7RYE-0rhI7tb2I8HQ8Wh0WcSsXWzP-5hvrR8gJZ-ecy_b7g1YVk_IDWfFas0qKln8kK8aYrmpWi0_kc0p_SqmYaFbk-ZKaME4QIbsHpCnv7EyDp3mL1M4eRmcSDT3FyY0YnaG82s42hsd5xLydh78758Pgnpx1HtMFvTmnm-D7EMciDB4GCuWYk3uxjMGHokmlaWma0OQYkglT8VrIQMscTUVXHjNkPKODKwveqmXKumGXcaF2y4J0RA56GBIev96H5O7qx-_Nz-r21_XN5vK2MkLKXEErFONGGQ5N0xqr6sYKJtdMmV412tQM2_a-BdXYlivUUjFEIdaS6bUUSstDcrr3mvLlFLHvpuhGiHPHWbcE35XguxJ8Ib_syQmSgaGP4I1Lb7iW9brRi_DbHvPRREwI0WzfcX79P_wKdZPt5T-XG6Jx</recordid><startdate>19870101</startdate><enddate>19870101</enddate><creator>KULINSKA, K</creator><creator>WIEWIOROWSKI, M</creator><general>NRC Research Press</general><general>National Research Council of Canada</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19870101</creationdate><title>A comparative study on the dynamics of epimeric 1-hydroxymethylquinolizidines: I. Conformational analysis of monomers and spectroscopic data for solid state, liquid state, and dilute solutions</title><author>KULINSKA, K ; WIEWIOROWSKI, M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c233t-a92701c7c1a559cd745d203607cf758c40e99b9a75d917e8370ee226308632783</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Atomic and molecular physics</topic><topic>Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics)</topic><topic>Exact sciences and technology</topic><topic>Molecular properties and interactions with photons</topic><topic>Physics</topic><topic>Properties of molecules and molecular ions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KULINSKA, K</creatorcontrib><creatorcontrib>WIEWIOROWSKI, M</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KULINSKA, K</au><au>WIEWIOROWSKI, M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A comparative study on the dynamics of epimeric 1-hydroxymethylquinolizidines: I. Conformational analysis of monomers and spectroscopic data for solid state, liquid state, and dilute solutions</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1987-01-01</date><risdate>1987</risdate><volume>65</volume><issue>1</issue><spage>205</spage><epage>212</epage><pages>205-212</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><coden>CJCHAG</coden><abstract>A systematic comparative study of the conformational dynamics of lupinine and epilupinine, two 1-hydroxymethyl quinolizidine epimers, as a function of phase transition and of their protonation is presented. Lupinine and epilupinine have a trans-quinolizidine configuration and they differ only in the position of the CH
2
OH group. The axial position of this group allows the formation of an intramolecular hydrogen bond OH ... N in lupinine, in contrast to epilupinine in which this group is in the equatorial position. Intrinsic conformational equilibria for both epimers have been defined. Despite the significant difference in the population of the preferred rotamers of lupinine and epilupinine, both epimers adopt very similar crystal structures, but in all other states and forms, e.g., pure liquids, solutions in inert and polar solvents, and protonated salts, they behave in drastically different ways.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v87-033</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 1987-01, Vol.65 (1), p.205-212 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_nrcresearch_primary_10_1139_v87_033 |
| source | NRC Research Press; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Atomic and molecular physics Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics) Exact sciences and technology Molecular properties and interactions with photons Physics Properties of molecules and molecular ions |
| title | A comparative study on the dynamics of epimeric 1-hydroxymethylquinolizidines: I. Conformational analysis of monomers and spectroscopic data for solid state, liquid state, and dilute solutions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-14T12%3A43%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pascalfrancis_nrcre&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20comparative%20study%20on%20the%20dynamics%20of%20epimeric%201-hydroxymethylquinolizidines:%20I.%20Conformational%20analysis%20of%20monomers%20and%20spectroscopic%20data%20for%20solid%20state,%20liquid%20state,%20and%20dilute%20solutions&rft.jtitle=Canadian%20journal%20of%20chemistry&rft.au=KULINSKA,%20K&rft.date=1987-01-01&rft.volume=65&rft.issue=1&rft.spage=205&rft.epage=212&rft.pages=205-212&rft.issn=0008-4042&rft.eissn=1480-3291&rft.coden=CJCHAG&rft_id=info:doi/10.1139/v87-033&rft_dat=%3Cpascalfrancis_nrcre%3E8346588%3C/pascalfrancis_nrcre%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |