Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2,2-diphenyl-1,3-dioxane
The structure of 5,5-bis(bromomethyl)-2,2-diphenyl-1,3-dioxane was studied by 1 H and 13 C NMR spectroscopy and X-ray analysis. Its molecules in crystal adopt a chair conformation, whereas equilibrium between energy-degenerate chair invertomers exists in solution at room temperature. According to th...
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| Veröffentlicht in: | Russian journal of organic chemistry 2020, Vol.56 (1), p.1-6 |
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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. Meshcheryakova, E. S. Khalilov, L. M. Kuznetsov, V. V. |
| description | The structure of 5,5-bis(bromomethyl)-2,2-diphenyl-1,3-dioxane was studied by
1
H and
13
C NMR spectroscopy and X-ray analysis. Its molecules in crystal adopt a
chair
conformation, whereas equilibrium between energy-degenerate
chair
invertomers exists in solution at room temperature. According to the low-temperature NMR data, the interconversion barrier amounts to 8.9 kcal/mol. The ring inversion path was simulated by DFT quantum chemical calculations using PBE/3ξ and (in some cases) RI-MP2/λ2 approximations, and the potential barrier to interconversion in different solvents was estimated by the cluster model. The calculated geometric parameters of the title compound were consistent with the experimental X-ray diffraction data, and the calculated interconversion barrier matched a cluster containing 5 molecules of methylene chloride in the nearest solvation shell of the substituted 1,3-dioxane molecule. |
| doi_str_mv | 10.1134/S1070428020010017 |
| format | Article |
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1
H and
13
C NMR spectroscopy and X-ray analysis. Its molecules in crystal adopt a
chair
conformation, whereas equilibrium between energy-degenerate
chair
invertomers exists in solution at room temperature. According to the low-temperature NMR data, the interconversion barrier amounts to 8.9 kcal/mol. The ring inversion path was simulated by DFT quantum chemical calculations using PBE/3ξ and (in some cases) RI-MP2/λ2 approximations, and the potential barrier to interconversion in different solvents was estimated by the cluster model. The calculated geometric parameters of the title compound were consistent with the experimental X-ray diffraction data, and the calculated interconversion barrier matched a cluster containing 5 molecules of methylene chloride in the nearest solvation shell of the substituted 1,3-dioxane molecule.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428020010017</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Chemistry ; Chemistry and Materials Science ; Clusters ; Computer simulation ; Conformational analysis ; Dichloromethane ; Low temperature ; NMR spectroscopy ; Organic Chemistry ; Potential barriers ; Quantum chemistry ; Room temperature ; Solvation ; X ray analysis</subject><ispartof>Russian journal of organic chemistry, 2020, Vol.56 (1), p.1-6</ispartof><rights>Pleiades Publishing, Ltd. 2020</rights><rights>2020© Pleiades Publishing, Ltd. 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-b130139c24d9d11cf45183e7e5eb14e2c7188f62685ac20dcccec7380bb558e53</citedby><cites>FETCH-LOGICAL-c316t-b130139c24d9d11cf45183e7e5eb14e2c7188f62685ac20dcccec7380bb558e53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428020010017$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428020010017$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</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>Meshcheryakova, E. S.</creatorcontrib><creatorcontrib>Khalilov, L. M.</creatorcontrib><creatorcontrib>Kuznetsov, V. V.</creatorcontrib><title>Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2,2-diphenyl-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)-2,2-diphenyl-1,3-dioxane was studied by
1
H and
13
C NMR spectroscopy and X-ray analysis. Its molecules in crystal adopt a
chair
conformation, whereas equilibrium between energy-degenerate
chair
invertomers exists in solution at room temperature. According to the low-temperature NMR data, the interconversion barrier amounts to 8.9 kcal/mol. The ring inversion path was simulated by DFT quantum chemical calculations using PBE/3ξ and (in some cases) RI-MP2/λ2 approximations, and the potential barrier to interconversion in different solvents was estimated by the cluster model. The calculated geometric parameters of the title compound were consistent with the experimental X-ray diffraction data, and the calculated interconversion barrier matched a cluster containing 5 molecules of methylene chloride in the nearest solvation shell of the substituted 1,3-dioxane molecule.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Clusters</subject><subject>Computer simulation</subject><subject>Conformational analysis</subject><subject>Dichloromethane</subject><subject>Low temperature</subject><subject>NMR spectroscopy</subject><subject>Organic Chemistry</subject><subject>Potential barriers</subject><subject>Quantum chemistry</subject><subject>Room temperature</subject><subject>Solvation</subject><subject>X ray analysis</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1UEtLw0AQXkTBWv0B3gJeFLo6s49kc6zFFxQ8VL2GZLOxKUm27ibQ_Hu3VPAgwjAPvgfDR8glwi0iF3crhAQEU8AAMFRyRCYYg6Kcp_w47AGme_yUnHm_AQCBgk_Ix6p3g-4HZ6K8K6OF7Srr2ryvbZc30Ty00dc-slUkZ5Le1_66cLa1renXY3ND2YzRst6uTTc2FGc8HHaXd-acnFR5483Fz5yS98eHt8UzXb4-vSzmS6o5xj0tkAPyVDNRpiWiroRExU1ipClQGKYTVKqKWaxkrhmUWmujE66gKKRURvIpuTr4bp39Gozvs40dXPjaZ4wnKhVcwp6FB5Z21ntnqmzr6jZ3Y4aQ7ePL_sQXNOyg8YHbfRr36_y_6Bu2jm8y</recordid><startdate>2020</startdate><enddate>2020</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>Meshcheryakova, 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></search><sort><creationdate>2020</creationdate><title>Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2,2-diphenyl-1,3-dioxane</title><author>Khazhiev, Sh. Yu ; Khusainov, M. A. ; Khalikov, R. A. ; Kataev, V. A. ; Tyumkina, T. V. ; Meshcheryakova, E. S. ; Khalilov, L. M. ; Kuznetsov, V. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-b130139c24d9d11cf45183e7e5eb14e2c7188f62685ac20dcccec7380bb558e53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Clusters</topic><topic>Computer simulation</topic><topic>Conformational analysis</topic><topic>Dichloromethane</topic><topic>Low temperature</topic><topic>NMR spectroscopy</topic><topic>Organic Chemistry</topic><topic>Potential barriers</topic><topic>Quantum chemistry</topic><topic>Room temperature</topic><topic>Solvation</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>Meshcheryakova, 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>Meshcheryakova, 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)-2,2-diphenyl-1,3-dioxane</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2020</date><risdate>2020</risdate><volume>56</volume><issue>1</issue><spage>1</spage><epage>6</epage><pages>1-6</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>The structure of 5,5-bis(bromomethyl)-2,2-diphenyl-1,3-dioxane was studied by
1
H and
13
C NMR spectroscopy and X-ray analysis. Its molecules in crystal adopt a
chair
conformation, whereas equilibrium between energy-degenerate
chair
invertomers exists in solution at room temperature. According to the low-temperature NMR data, the interconversion barrier amounts to 8.9 kcal/mol. The ring inversion path was simulated by DFT quantum chemical calculations using PBE/3ξ and (in some cases) RI-MP2/λ2 approximations, and the potential barrier to interconversion in different solvents was estimated by the cluster model. The calculated geometric parameters of the title compound were consistent with the experimental X-ray diffraction data, and the calculated interconversion barrier matched a cluster containing 5 molecules of methylene chloride in the nearest solvation shell of the substituted 1,3-dioxane molecule.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428020010017</doi><tpages>6</tpages></addata></record> |
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| subjects | Chemistry Chemistry and Materials Science Clusters Computer simulation Conformational analysis Dichloromethane Low temperature NMR spectroscopy Organic Chemistry Potential barriers Quantum chemistry Room temperature Solvation X ray analysis |
| title | Structure and Conformational Analysis of 5,5-Bis(bromomethyl)-2,2-diphenyl-1,3-dioxane |
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