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Butterfly Methanes: Designing a Novel Class of anti‐van′t Hoff Carbons
Author(s) -
Saumya M. J.,
Raghi K. R.,
Sherin D. R.,
Haridas K. R,
Manojkumar T. K.
Publication year - 2020
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202000501
Subject(s) - tetracoordinate , chemistry , carbon fibers , natural bond orbital , density functional theory , planar , molecular orbital , computational chemistry , atomic orbital , molecule , acceptor , crystallography , materials science , organic chemistry , electron , physics , condensed matter physics , computer graphics (images) , quantum mechanics , composite number , computer science , composite material
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 2 , −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.