Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 6, Pages 1486-1491Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100167
Keywords
organoboron compounds; conformational analysis; electron delocalization; quantum-chemical calculations
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Funding
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) [001]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [301371/2017-2]
- Fundacao de Amparo a Pesquisa do Estado de Minas Gerais (FAPEMIG)
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The study focused on the conformational behavior and boron hybridization in beta-substituted ethylboranes, with findings showing that the B-H bond tends to overlap with the C-C bond, and that the stability of conformers in 2-aminoethylborane is influenced by the substituent X.
The chemistry of boron-containing molecules pervades the study of biomolecules, new materials, organic synthesis, and beyond. In addition, the stereochemistry and rehybridization capability of boron in molecules influence the reactivity and selectivity of reactions. Therefore, conformational analysis and the study of substituent effects on the modulation of the sp(2)-sp(3) character of boron in beta-substituted ethylboranes may be valuable for the rational design of compounds in which the empty p(B) orbital plays a central role in the reaction intermediate. Accordingly, we have quantum-chemically studied the orbital interactions and bonding properties that govern the conformational behavior and boron hybridization in beta-substituted ethylboranes (substituents, X=H, CH3, F, Cl, NH2, PH2, OH, and SH). Conformations with an anti arrangement along the B-C-C-X path are generally preferred over syn and/or gauche conformations, while a B-H bond tends to eclipse with the C-C bond rather than with a less sterically hindered C-H bond. However, the s character of boron relative to the C-B bond strongly decreases in the syn conformation, where X can participate as an electron donor to the empty p(B) orbital. Indeed, such interaction makes the syn conformation of 2-aminoethylborane the single stable conformer in the gas phase.
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