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In Silico Studies on Selected Neutral Molecules, CGa2Ge2, CAlGaGe2, and CSiGa2Ge Containing Planar Tetracoordinate Carbon
Article

Stereomutation in Tetracoordinate Centers via Stabilization of Planar Tetracoordinated Systems

1
School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, HBNI, P.O. Jatni, Khurda 752050, India
2
Center for Computational Natural Sciences, Bioinformatics International Institute of Information Technology, Hyderabad 500032, India
*
Authors to whom correspondence should be addressed.
Academic Editors: Venkatesan S. Thimmakondu and Krishnan Thirumoorthy
Atoms 2021, 9(4), 79; https://doi.org/10.3390/atoms9040079
Received: 29 August 2021 / Revised: 3 October 2021 / Accepted: 7 October 2021 / Published: 14 October 2021
(This article belongs to the Special Issue Planar Tetracoordinate Carbon—Fifty Years and Beyond)
The quest for stabilizing planar forms of tetracoordinate carbon started five decades ago and intends to achieve interconversion between [R]- and [S]-stereoisomers without breaking covalent bonds. Several strategies are successful in making the planar tetracoordinate form a minimum on its potential energy surface. However, the first examples of systems where stereomutation is possible were reported only recently. In this study, the possibility of neutral and dications of simple hydrocarbons (cyclopentane, cyclopentene, spiropentane, and spiropentadiene) and their counterparts with the central carbon atom replaced by elements from groups 13, 14, and 15 are explored using ab initio MP2 calculations. The energy difference between the tetrahedral and planar forms decreases from row II to row III or IV substituents. Additionally, aromaticity involving the delocalization of the lone pair on the central atom appears to help in further stabilizing the planar form compared to the tetrahedral form, especially for the row II substituents. We identified 11 systems where the tetrahedral state is a minimum on the potential energy surface, and the planar form is a transition state corresponding to stereomutation. Interestingly, the planar structures of three systems were found to be minimum, and the corresponding tetrahedral states were transition states. The energy profiles corresponding to such transitions involving both planar and tetrahedral states without the breaking of covalent bonds were examined. The systems showcased in this study and research in this direction are expected to realize molecules that experimentally exhibit stereomutation. View Full-Text
Keywords: stereomutation; planar tetracoordinate compounds; stereochemistry; aromaticity; otential energy surface stereomutation; planar tetracoordinate compounds; stereochemistry; aromaticity; otential energy surface
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MDPI and ACS Style

Yadav, K.; Lourderaj, U.; Priyakumar, U.D. Stereomutation in Tetracoordinate Centers via Stabilization of Planar Tetracoordinated Systems. Atoms 2021, 9, 79. https://doi.org/10.3390/atoms9040079

AMA Style

Yadav K, Lourderaj U, Priyakumar UD. Stereomutation in Tetracoordinate Centers via Stabilization of Planar Tetracoordinated Systems. Atoms. 2021; 9(4):79. https://doi.org/10.3390/atoms9040079

Chicago/Turabian Style

Yadav, Komal, Upakarasamy Lourderaj, and U. D. Priyakumar 2021. "Stereomutation in Tetracoordinate Centers via Stabilization of Planar Tetracoordinated Systems" Atoms 9, no. 4: 79. https://doi.org/10.3390/atoms9040079

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