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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Sakai, Tomoko Abe, Manabu Mizuta, Tsutomu Nakagaki, Tomoyuki Fujiwara, Yoshihisa |
| Description | Author Affiliation: Nakagaki T ( Department of Chemistry, Graduate School of Science, Hiroshima University (HIRODAI), 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.) |
| Abstract | Kinetic stabilization and reactivity of π single-bonded species have been investigated in detail by generating a series of singlet 2,2-dialkoxy-1,3-diphenyloctahydropentalene-1,3-diyls (DRs). The lifetime at 293 K in benzene was found to increase when the carbon chain length of the alkoxy groups was increased; 292 ns (DRb; $OR=OR′=OCH_{3})$ <880 ns (DRc; $OR=OR′=OC_{2}H_{5})$ <1899 ns (DRd; $OR=OR′=OC_{3}H_{7})$ ≈2292 ns (DRe; $OR=OR′=OC_{6}H_{13})$ ≈2146 ns (DRf; $OR=OR′=OC_{10}H_{21}).$ DRh $(OR=OC_{3}H_{7},$ $OR′=OCH_{3};$ 935 ns) with the mixed-acetal moiety is a longer-lived species than another diastereomer DRg $(OR=OCH_{3},$ $OR′=OC_{3}H_{7};$ 516 ns). Activation parameters determined for the first-order decay process reveal that the enthalpy factor plays a crucial role in determining the energy barrier of the ring-closing reaction, that is, from the π-bonding to the σ-bonding compounds. Computational studies using density functional theory provided more insight into the structures of the singlet species with π single-bonded character and the transition states for the ring-closing reaction, thereby clarifying the role of the alkoxy group on the lifetime and the stereoselectivity of the ring-closing reaction. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 31 |
| Volume Number | 19 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2013-07-29 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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