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http://dx.doi.org/10.5012/bkcs.2011.32.9.3372

Determination of Atomic Structures and Relative Stabilities of Diadduct Regioisomers of C20X2 (X = H, F, Cl, Br, and OH) by the Hybrid Density-Functional B3LYP Method  

Lee, Seol (Department of Chemistry, and Nanoscale Sciences and Technology Institute, Wonkwang University)
Suh, Young-Sun (Department of Chemistry, and Nanoscale Sciences and Technology Institute, Wonkwang University)
Hwang, Yong-Gyoo (Division of Microelectronics and Display Technology, and Nanoscale Sciences and Technology Institute, Wonkwang University)
Lee, Kee-Hag (Department of Chemistry, and Nanoscale Sciences and Technology Institute, Wonkwang University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.9, 2011 , pp. 3372-3376 More about this Journal
Abstract
We have studied the relative stability and atomic structures of five $C_{20}X_2$ regioisomers obtained as diadducts of a $C_{20}$ cage (X = H, F, Cl, Br, and OH). All the regioisomers are geometric isomers, i.e., they differ in their spatial arrangement. Full-geometry optimizations of the regioisomers have been performed using the hybrid density-functional (B3LYP/6-31G(d, p)) method. Our results suggest that the cis-1 regioisomer (the 1,2-diadduct) is the most stable and that the second most stable is the trans-2 (1,13-diadduct) regioisomer, implying that the long-range interaction between the two adducts and the resonance effect are more pronounced than the diadduct-induced strain in the $C_{20}$ cage. The HOMO and LUMO characteristics of each regioisomer with the same symmetry of structural regioisomers except $C_{20}(OH)_2$ are topologically same. This suggests that by using an entirely different set of characteristic chemical reactions for each regioisomer, we can distinguish between the five regioisomers for each $C_{20}$ diadduct derivative.
Keywords
$C_{20}$ diadducts (dihydride, dihydroxide, and dihalides); $C_{20}X_2$ regioisomers; Hybrid density-functional (B3LYP) calculations; HOMO and LUMO;
Citations & Related Records
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Times Cited By Web Of Science : 2  (Related Records In Web of Science)
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