Butterfly Methanes: Designing a Novel Class of anti-van't Hoff Carbons

Among different possible non-classical structures, the stabilization of half-planar tetracoordinate carbon conformation is believed to be the most difficult one. Herein, we designed three types of half-planar tetracoordinate carbon compounds computationally by employing hybrid stabilization effects...

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Published in:Chemphyschem 2020-10, Vol.21 (20), p.2272-2278
Main Authors: Saumya, M J, Raghi, K R, Sherin, D R, Haridas, K R, Manojkumar, T K
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Raghi, K R
Sherin, D R
Haridas, K R
Manojkumar, T K
description Among different possible non-classical structures, the stabilization of half-planar tetracoordinate carbon conformation is believed to be the most difficult one. Herein, we designed three types of half-planar tetracoordinate carbon compounds computationally by employing hybrid stabilization effects of substituents. The axial hydrogens of unstable half-planar methane are substituted with π-acceptor and σ-donor substituents such as -BH , -Li and the equatorial substituents selected are a combination of electropositive atoms (σ-donors)/electronegative atoms (σ-acceptors and π-donors). To establish the stabilization factors, we conducted a detailed study on vibrational frequency analysis, molecular orbital analysis (including Natural Bond Orbitals) and electrostatic potential (ESP) analysis of optimized molecular geometries using density functional theory.
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