Conformational Analysis of 1,2:3,4-Diepoxides: Ab Initio and semiempirical molecular-orbital calculations |
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Authors: | Martin Nikles,Daniel Bur,Urs S quin,Hanspeter Huber |
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Affiliation: | Martin Nikles,Daniel Bur,Urs Séquin,Hanspeter Huber |
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Abstract: | Using semiempirical and ab initio procedures, the most stable conformations of meso- and rac-bioxirane and of some substituted 1,2:3,4-diepoxides were calculated. For threo-diepoxides (having the same relative configurations as rac-bioxirane, 3 ), two stable conformations with CCCC dihedral angles of ca. 90 and ca. 270° were found. For erythro-diepoxides (derivatives of meso-bioxirane, 4 ) the calculations suggest three preferred conformations with corresponding dihedral CCCC angles of ca. 90°, ca. 180°, and ca. 270°. The calculations are in fair agreement with the experimental data available for the unsubstituted compounds 3 and 4 . |
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