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Butterfly Methanes: Designing a Novel Class of anti-van′t Hoff Carbons |
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| Authors: | M J Saumya K R Raghi D R Sherin K R Haridas T K Manojkumar |
| Institution: | 1. School of Chemical Sciences, Kannur University, Payyanur Campus, Edat P.O, Kannur, 670327 Kerala, India
Indian Institute of Information Technology and Management-Kerala Technopark Campus, Trivandrum, 695581 Kerala, India These authors contributed equally to this work.;2. Indian Institute of Information Technology and Management-Kerala Technopark Campus, Trivandrum, 695581 Kerala, India;3. School of Chemical Sciences, Kannur University, Payyanur Campus, Edat P.O, Kannur, 670327 Kerala, India |
| Abstract: | 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 −BH2, −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. |
| Keywords: | butterfly carbon density functional calculations half-planar methane non-classical carbon stabilization effects |