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Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by 1 H NMR spectroscopy and molecular simulation
Based on 1 H NMR spectral analysis combined with molecular simulation, conformational states of the cyclohexanone ring were studied for some 1 R ,4 S ‐2‐(4‐X‐benzylidene)‐ p ‐menthan‐3‐ones (X = COOCH 3 or C 6 H 5 ) in CDCl 3 and C 6 D 6 . The co‐existence of chair conformers with an axial orientati...
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| Published in: | Magnetic resonance in chemistry 2002-09, Vol.40 (9), p.566-572 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c728-e0ed1c34d45c4c20bea2f08ec017eb0bd977de4649ad7e34b5dbfce522872d9c3 |
| container_end_page | 572 |
| container_issue | 9 |
| container_start_page | 566 |
| container_title | Magnetic resonance in chemistry |
| container_volume | 40 |
| creator | Pivnenko, Nikolay S. Drushlyak, Tatyana G. Kutulya, Lidiya A. Vashchenko, Valeriy V. Doroshenko, Andrey O. Goodby, John W. |
| description | Based on
1
H NMR spectral analysis combined with molecular simulation, conformational states of the cyclohexanone ring were studied for some 1
R
,4
S
‐2‐(4‐X‐benzylidene)‐
p
‐menthan‐3‐ones (X = COOCH
3
or C
6
H
5
) in CDCl
3
and C
6
D
6
. The co‐existence of chair conformers with an axial orientation of both alkyl substituents and twist‐boat forms was established for the compounds studied at room temperature (22–23° C). The substituent X does not influence appreciably the ratio of these conformers, but the fraction of twist‐boat forms increases noticeably in benzene solutions as compared with CDCl
3
solutions. Rotameric states of the isopropyl fragment were also characterised for the compounds studied. Distinctions in conformational states for the 1
R
,4
S
‐2‐arylidene‐
p
‐menthan‐3‐ones and (−)‐menthone were revealed and are discussed. Copyright © 2002 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/mrc.1068 |
| format | article |
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1
H NMR spectral analysis combined with molecular simulation, conformational states of the cyclohexanone ring were studied for some 1
R
,4
S
‐2‐(4‐X‐benzylidene)‐
p
‐menthan‐3‐ones (X = COOCH
3
or C
6
H
5
) in CDCl
3
and C
6
D
6
. The co‐existence of chair conformers with an axial orientation of both alkyl substituents and twist‐boat forms was established for the compounds studied at room temperature (22–23° C). The substituent X does not influence appreciably the ratio of these conformers, but the fraction of twist‐boat forms increases noticeably in benzene solutions as compared with CDCl
3
solutions. Rotameric states of the isopropyl fragment were also characterised for the compounds studied. Distinctions in conformational states for the 1
R
,4
S
‐2‐arylidene‐
p
‐menthan‐3‐ones and (−)‐menthone were revealed and are discussed. Copyright © 2002 John Wiley & Sons, Ltd.</description><identifier>ISSN: 0749-1581</identifier><identifier>EISSN: 1097-458X</identifier><identifier>DOI: 10.1002/mrc.1068</identifier><language>eng</language><ispartof>Magnetic resonance in chemistry, 2002-09, Vol.40 (9), p.566-572</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c728-e0ed1c34d45c4c20bea2f08ec017eb0bd977de4649ad7e34b5dbfce522872d9c3</citedby><cites>FETCH-LOGICAL-c728-e0ed1c34d45c4c20bea2f08ec017eb0bd977de4649ad7e34b5dbfce522872d9c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Pivnenko, Nikolay S.</creatorcontrib><creatorcontrib>Drushlyak, Tatyana G.</creatorcontrib><creatorcontrib>Kutulya, Lidiya A.</creatorcontrib><creatorcontrib>Vashchenko, Valeriy V.</creatorcontrib><creatorcontrib>Doroshenko, Andrey O.</creatorcontrib><creatorcontrib>Goodby, John W.</creatorcontrib><title>Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by 1 H NMR spectroscopy and molecular simulation</title><title>Magnetic resonance in chemistry</title><description>Based on
1
H NMR spectral analysis combined with molecular simulation, conformational states of the cyclohexanone ring were studied for some 1
R
,4
S
‐2‐(4‐X‐benzylidene)‐
p
‐menthan‐3‐ones (X = COOCH
3
or C
6
H
5
) in CDCl
3
and C
6
D
6
. The co‐existence of chair conformers with an axial orientation of both alkyl substituents and twist‐boat forms was established for the compounds studied at room temperature (22–23° C). The substituent X does not influence appreciably the ratio of these conformers, but the fraction of twist‐boat forms increases noticeably in benzene solutions as compared with CDCl
3
solutions. Rotameric states of the isopropyl fragment were also characterised for the compounds studied. Distinctions in conformational states for the 1
R
,4
S
‐2‐arylidene‐
p
‐menthan‐3‐ones and (−)‐menthone were revealed and are discussed. Copyright © 2002 John Wiley & Sons, Ltd.</description><issn>0749-1581</issn><issn>1097-458X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNotUMFKxDAQDaLgugp-Qo4erE7SdNMcZVFXWBXWPXgraTLFStOUpB568-Ldb_RLTNHDm_cYmDczj5BzBlcMgF-7YJJYlQdkwUDJTBTl6yFZgBQqY0XJjslJjO8AoJTMF-Rr7fvGB6fH1ve6ozqVKbaR-oZG75AyuqOXgr7Qn89vnqDD1LUWe0yaDnPXYT--6T6pPMH3GGk9pbkNfXrc0TigGYOPxg9TcrfU-Q7NR6cDja1LPC8-JUeN7iKe_fOS7O9u9-tNtn2-f1jfbDMjeZkhoGUmF1YURhgONWreQIkGmMQaaquktChWQmkrMRd1YevGYMF5KblVJl-Siz9bkw6KAZtqCK1LH1UMqjm9KqVXzenlv4qfaYI</recordid><startdate>200209</startdate><enddate>200209</enddate><creator>Pivnenko, Nikolay S.</creator><creator>Drushlyak, Tatyana G.</creator><creator>Kutulya, Lidiya A.</creator><creator>Vashchenko, Valeriy V.</creator><creator>Doroshenko, Andrey O.</creator><creator>Goodby, John W.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200209</creationdate><title>Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by 1 H NMR spectroscopy and molecular simulation</title><author>Pivnenko, Nikolay S. ; Drushlyak, Tatyana G. ; Kutulya, Lidiya A. ; Vashchenko, Valeriy V. ; Doroshenko, Andrey O. ; Goodby, John W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c728-e0ed1c34d45c4c20bea2f08ec017eb0bd977de4649ad7e34b5dbfce522872d9c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pivnenko, Nikolay S.</creatorcontrib><creatorcontrib>Drushlyak, Tatyana G.</creatorcontrib><creatorcontrib>Kutulya, Lidiya A.</creatorcontrib><creatorcontrib>Vashchenko, Valeriy V.</creatorcontrib><creatorcontrib>Doroshenko, Andrey O.</creatorcontrib><creatorcontrib>Goodby, John W.</creatorcontrib><collection>CrossRef</collection><jtitle>Magnetic resonance in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pivnenko, Nikolay S.</au><au>Drushlyak, Tatyana G.</au><au>Kutulya, Lidiya A.</au><au>Vashchenko, Valeriy V.</au><au>Doroshenko, Andrey O.</au><au>Goodby, John W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by 1 H NMR spectroscopy and molecular simulation</atitle><jtitle>Magnetic resonance in chemistry</jtitle><date>2002-09</date><risdate>2002</risdate><volume>40</volume><issue>9</issue><spage>566</spage><epage>572</epage><pages>566-572</pages><issn>0749-1581</issn><eissn>1097-458X</eissn><abstract>Based on
1
H NMR spectral analysis combined with molecular simulation, conformational states of the cyclohexanone ring were studied for some 1
R
,4
S
‐2‐(4‐X‐benzylidene)‐
p
‐menthan‐3‐ones (X = COOCH
3
or C
6
H
5
) in CDCl
3
and C
6
D
6
. The co‐existence of chair conformers with an axial orientation of both alkyl substituents and twist‐boat forms was established for the compounds studied at room temperature (22–23° C). The substituent X does not influence appreciably the ratio of these conformers, but the fraction of twist‐boat forms increases noticeably in benzene solutions as compared with CDCl
3
solutions. Rotameric states of the isopropyl fragment were also characterised for the compounds studied. Distinctions in conformational states for the 1
R
,4
S
‐2‐arylidene‐
p
‐menthan‐3‐ones and (−)‐menthone were revealed and are discussed. Copyright © 2002 John Wiley & Sons, Ltd.</abstract><doi>10.1002/mrc.1068</doi><tpages>7</tpages></addata></record> |
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| source | Wiley |
| title | Conformational analysis of some 1 R ,4 S ‐2‐arylidene‐ p ‐menthan‐3‐ones by 1 H NMR spectroscopy and molecular simulation |
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