Structure and Conformational Analysis of 5,5-Bis(bromomethyl)- 2-(4-chlorophenyl)-2-methyl-1,3-dioxane
The structure of 5,5-bis(bromomethyl)-2-(4-chlorophenyl)-2-methyl-1,3-dioxane was studied by 1 H and 13 C NMR spectroscopy and X-ray analysis. The compound was found to exist in crystal and solution as a chair conformer with the axial aromatic substituent. The conformational transformation pathway a...
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| Veröffentlicht in: | Russian journal of organic chemistry 2024, Vol.60 (1), p.25-32 |
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| container_title | Russian journal of organic chemistry |
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| creator | Khazhiev, Sh. Yu Khusainov, M. A. Khalikov, R. A. Kataev, V. A. Tyumkina, T. V. Mescheryakova, E. S. Khalilov, L. M. Kuznetsov, V. V. |
| description | The structure of 5,5-bis(bromomethyl)-2-(4-chlorophenyl)-2-methyl-1,3-dioxane was studied by
1
H and
13
C NMR spectroscopy and X-ray analysis. The compound was found to exist in crystal and solution as a
chair
conformer with the axial aromatic substituent. The conformational transformation pathway and potential energy barriers to internal rotation of the aromatic substituent for the isolated molecule and solutions in chloroform and benzene (cluster model) were determined by DFT calculations using PBE functional and 3ξ and def2-SVP basis sets. |
| doi_str_mv | 10.1134/S1070428024010044 |
| format | Article |
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1
H and
13
C NMR spectroscopy and X-ray analysis. The compound was found to exist in crystal and solution as a
chair
conformer with the axial aromatic substituent. The conformational transformation pathway and potential energy barriers to internal rotation of the aromatic substituent for the isolated molecule and solutions in chloroform and benzene (cluster model) were determined by DFT calculations using PBE functional and 3ξ and def2-SVP basis sets.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428024010044</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Benzene ; Chemistry ; Chemistry and Materials Science ; Chloroform ; Conformational analysis ; NMR spectroscopy ; Organic Chemistry ; Potential energy ; X ray analysis</subject><ispartof>Russian journal of organic chemistry, 2024, Vol.60 (1), p.25-32</ispartof><rights>Pleiades Publishing, Ltd. 2024</rights><rights>Pleiades Publishing, Ltd. 2024.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c268t-5aeade185b16da42470d551461632813f3e963f7b1687245f4faa98a4acc9603</cites><orcidid>0000-0003-2926-3309 ; 0000-0001-8127-9135 ; 0000-0002-3021-761X ; 0000-0003-4498-2598 ; 0000-0001-9401-8153 ; 0000-0001-8351-0601 ; 0000-0002-2095-9097 ; 0000-0003-1040-8475</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428024010044$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428024010044$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51298</link.rule.ids></links><search><creatorcontrib>Khazhiev, Sh. Yu</creatorcontrib><creatorcontrib>Khusainov, M. A.</creatorcontrib><creatorcontrib>Khalikov, R. A.</creatorcontrib><creatorcontrib>Kataev, V. A.</creatorcontrib><creatorcontrib>Tyumkina, T. V.</creatorcontrib><creatorcontrib>Mescheryakova, E. S.</creatorcontrib><creatorcontrib>Khalilov, L. M.</creatorcontrib><creatorcontrib>Kuznetsov, V. V.</creatorcontrib><title>Structure and Conformational Analysis of 5,5-Bis(bromomethyl)- 2-(4-chlorophenyl)-2-methyl-1,3-dioxane</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>The structure of 5,5-bis(bromomethyl)-2-(4-chlorophenyl)-2-methyl-1,3-dioxane was studied by
1
H and
13
C NMR spectroscopy and X-ray analysis. The compound was found to exist in crystal and solution as a
chair
conformer with the axial aromatic substituent. The conformational transformation pathway and potential energy barriers to internal rotation of the aromatic substituent for the isolated molecule and solutions in chloroform and benzene (cluster model) were determined by DFT calculations using PBE functional and 3ξ and def2-SVP basis sets.</description><subject>Benzene</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chloroform</subject><subject>Conformational analysis</subject><subject>NMR spectroscopy</subject><subject>Organic Chemistry</subject><subject>Potential energy</subject><subject>X ray analysis</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kMtqwzAQRUVpoenjA7ozdJNC1M5Isiwv09AXBLpI9kaxpcbBtlLJhubvq-BCF6WbmWHOvRdmCLlBuEfk4mGFkIFgCpgABBDihExQgqKc5_w0zhHTIz8nFyHsIEpQ8Amxq94PZT94k-iuShaus863uq9dp5tkHssh1CFxNklnKX2sw3TjXeta028PzR1NGJ0KWm4b591-a7rjjtGRUpxxWtXuS3fmipxZ3QRz_dMvyfr5ab14pcv3l7fFfElLJlVPU210ZVClG5SVFkxkUKUpComSM4XccpNLbrOIVcZEaoXVOlda6LLMJfBLcjvG7r37HEzoi50bfDwiFByEzDgoVFGFo6r0LgRvbLH3dav9oUAojt8s_nwzetjoCVHbfRj_m_y_6RsHUXPc</recordid><startdate>2024</startdate><enddate>2024</enddate><creator>Khazhiev, Sh. Yu</creator><creator>Khusainov, M. A.</creator><creator>Khalikov, R. A.</creator><creator>Kataev, V. A.</creator><creator>Tyumkina, T. V.</creator><creator>Mescheryakova, E. S.</creator><creator>Khalilov, L. M.</creator><creator>Kuznetsov, V. V.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2926-3309</orcidid><orcidid>https://orcid.org/0000-0001-8127-9135</orcidid><orcidid>https://orcid.org/0000-0002-3021-761X</orcidid><orcidid>https://orcid.org/0000-0003-4498-2598</orcidid><orcidid>https://orcid.org/0000-0001-9401-8153</orcidid><orcidid>https://orcid.org/0000-0001-8351-0601</orcidid><orcidid>https://orcid.org/0000-0002-2095-9097</orcidid><orcidid>https://orcid.org/0000-0003-1040-8475</orcidid></search><sort><creationdate>2024</creationdate><title>Structure and Conformational Analysis of 5,5-Bis(bromomethyl)- 2-(4-chlorophenyl)-2-methyl-1,3-dioxane</title><author>Khazhiev, Sh. Yu ; Khusainov, M. A. ; Khalikov, R. A. ; Kataev, V. A. ; Tyumkina, T. V. ; Mescheryakova, E. S. ; Khalilov, L. M. ; Kuznetsov, V. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c268t-5aeade185b16da42470d551461632813f3e963f7b1687245f4faa98a4acc9603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Benzene</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chloroform</topic><topic>Conformational analysis</topic><topic>NMR spectroscopy</topic><topic>Organic Chemistry</topic><topic>Potential energy</topic><topic>X ray analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khazhiev, Sh. Yu</creatorcontrib><creatorcontrib>Khusainov, M. A.</creatorcontrib><creatorcontrib>Khalikov, R. A.</creatorcontrib><creatorcontrib>Kataev, V. A.</creatorcontrib><creatorcontrib>Tyumkina, T. V.</creatorcontrib><creatorcontrib>Mescheryakova, E. S.</creatorcontrib><creatorcontrib>Khalilov, L. M.</creatorcontrib><creatorcontrib>Kuznetsov, V. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khazhiev, Sh. Yu</au><au>Khusainov, M. A.</au><au>Khalikov, R. A.</au><au>Kataev, V. A.</au><au>Tyumkina, T. V.</au><au>Mescheryakova, E. S.</au><au>Khalilov, L. M.</au><au>Kuznetsov, V. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure and Conformational Analysis of 5,5-Bis(bromomethyl)- 2-(4-chlorophenyl)-2-methyl-1,3-dioxane</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2024</date><risdate>2024</risdate><volume>60</volume><issue>1</issue><spage>25</spage><epage>32</epage><pages>25-32</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>The structure of 5,5-bis(bromomethyl)-2-(4-chlorophenyl)-2-methyl-1,3-dioxane was studied by
1
H and
13
C NMR spectroscopy and X-ray analysis. The compound was found to exist in crystal and solution as a
chair
conformer with the axial aromatic substituent. The conformational transformation pathway and potential energy barriers to internal rotation of the aromatic substituent for the isolated molecule and solutions in chloroform and benzene (cluster model) were determined by DFT calculations using PBE functional and 3ξ and def2-SVP basis sets.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428024010044</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-2926-3309</orcidid><orcidid>https://orcid.org/0000-0001-8127-9135</orcidid><orcidid>https://orcid.org/0000-0002-3021-761X</orcidid><orcidid>https://orcid.org/0000-0003-4498-2598</orcidid><orcidid>https://orcid.org/0000-0001-9401-8153</orcidid><orcidid>https://orcid.org/0000-0001-8351-0601</orcidid><orcidid>https://orcid.org/0000-0002-2095-9097</orcidid><orcidid>https://orcid.org/0000-0003-1040-8475</orcidid></addata></record> |
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| subjects | Benzene Chemistry Chemistry and Materials Science Chloroform Conformational analysis NMR spectroscopy Organic Chemistry Potential energy X ray analysis |
| title | Structure and Conformational Analysis of 5,5-Bis(bromomethyl)- 2-(4-chlorophenyl)-2-methyl-1,3-dioxane |
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