Absolute configuration determination of donor–acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra
Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7‐bis(methoxycarbonyl)‐12,15‐dimethoxy‐[2.2]paracyclophanes (1 and 2), and density functional theory (DFT) calculations were performed at the B3LYP/6‐31G(d) level for all...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2006, Vol.18 (3), p.205-211 |
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| container_title | Chirality (New York, N.Y.) |
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| creator | Furo, Takahiro Mori, Tadashi Origane, Yumi Wada, Takehiko Izumi, Hiroshi Inoue, Yoshihisa |
| description | Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7‐bis(methoxycarbonyl)‐12,15‐dimethoxy‐[2.2]paracyclophanes (1 and 2), and density functional theory (DFT) calculations were performed at the B3LYP/6‐31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)‐enantiomers as (4Sp;12Sp)‐1 and (4Sp;12Rp)‐2, respectively. © 2006 Wiley‐Liss, Inc. Chirality |
| doi_str_mv | 10.1002/chir.20233 |
| format | Article |
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Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)‐enantiomers as (4Sp;12Sp)‐1 and (4Sp;12Rp)‐2, respectively. © 2006 Wiley‐Liss, Inc. 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Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)‐enantiomers as (4Sp;12Sp)‐1 and (4Sp;12Rp)‐2, respectively. © 2006 Wiley‐Liss, Inc. Chirality</description><subject>charge‐transfer interaction</subject><subject>chiral cyclophane</subject><subject>DFT calculation</subject><subject>exciton coupling method</subject><subject>vibrational circular dichroism spectroscopy</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp9kcFu1DAQhi0EokvhwgMgnzggZbHHaRIfqxXQSpWQUA-VEIqc8Zg1SuJgO7R74x14Ax6NJyElK3HryePRN99o9DP2UoqtFALe4t7HLQhQ6hHbyDMQRaWqm8dsIxqtCyFKOGHPUvomhNCVKp-yE1mVCjTAhv0-71Lo50wcw-j81zma7MPILWWKgx_XX3DchjHEPz9_GUSacoj8M2zhy2SiwQP2YdqbkRLvDotnWLo-rWN5TyFS9mh6bkbL6W6i6Aca89L44bt13VKjjzj3JnLrcR-DTwNPE2GO5jl74kyf6MXxPWXX799d7y6Kq48fLnfnVwUqrVTRiKYzsrGNM4KUcBZKR7qGxlZKQe1AVB3VZ4ZA6hKl6GqHKAErrZ2zWp2y16t2iuH7TCm3g09Ifb8cFubUVnXdQAP1Ar5ZQYwhpUiunZaLTDy0UrT3gbT3gbT_AlngV0fr3A1k_6PHBBZArsCt7-nwgKrdXVx-WqV_AUhknIU</recordid><startdate>2006</startdate><enddate>2006</enddate><creator>Furo, Takahiro</creator><creator>Mori, Tadashi</creator><creator>Origane, Yumi</creator><creator>Wada, Takehiko</creator><creator>Izumi, Hiroshi</creator><creator>Inoue, Yoshihisa</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>2006</creationdate><title>Absolute configuration determination of donor–acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra</title><author>Furo, Takahiro ; Mori, Tadashi ; Origane, Yumi ; Wada, Takehiko ; Izumi, Hiroshi ; Inoue, Yoshihisa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3933-808ba18d8fa0e30fd24fe9728d63327f206be75ae2194c10b7fcc12c699ffd93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>charge‐transfer interaction</topic><topic>chiral cyclophane</topic><topic>DFT calculation</topic><topic>exciton coupling method</topic><topic>vibrational circular dichroism spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Furo, Takahiro</creatorcontrib><creatorcontrib>Mori, Tadashi</creatorcontrib><creatorcontrib>Origane, Yumi</creatorcontrib><creatorcontrib>Wada, Takehiko</creatorcontrib><creatorcontrib>Izumi, Hiroshi</creatorcontrib><creatorcontrib>Inoue, Yoshihisa</creatorcontrib><collection>PubMed</collection><collection>CrossRef</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>Furo, Takahiro</au><au>Mori, Tadashi</au><au>Origane, Yumi</au><au>Wada, Takehiko</au><au>Izumi, Hiroshi</au><au>Inoue, Yoshihisa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Absolute configuration determination of donor–acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2006</date><risdate>2006</risdate><volume>18</volume><issue>3</issue><spage>205</spage><epage>211</epage><pages>205-211</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>Vibrational circular dichroism (VCD) spectra were obtained for the assignments of the absolute configurations of diastereomeric 4,7‐bis(methoxycarbonyl)‐12,15‐dimethoxy‐[2.2]paracyclophanes (1 and 2), and density functional theory (DFT) calculations were performed at the B3LYP/6‐31G(d) level for all possible conformations of both 1 and 2 to give the theoretical VCD spectra. Comparisons of the experimental and theoretical VCD spectra obtained unambiguously established the absolute configurations of the dextrorotatory (+)‐enantiomers as (4Sp;12Sp)‐1 and (4Sp;12Rp)‐2, respectively. © 2006 Wiley‐Liss, Inc. Chirality</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc., A Wiley Company</pub><pmid>16432922</pmid><doi>10.1002/chir.20233</doi><tpages>7</tpages></addata></record> |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | charge‐transfer interaction chiral cyclophane DFT calculation exciton coupling method vibrational circular dichroism spectroscopy |
| title | Absolute configuration determination of donor–acceptor [2.2]paracyclophanes by comparison of theoretical and experimental vibrational circular dichroism spectra |
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