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Tetrel Bond between 6-OTX3-Fulvene and NH3: Substituents and Aromaticity

1
The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
2
School of Ocean, Shandong University, Weihai 264209, China
3
Shandong Key Laboratory of Biochemical Analysis, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Antonio Caballero
Molecules 2019, 24(1), 10; https://doi.org/10.3390/molecules24010010
Received: 3 December 2018 / Revised: 16 December 2018 / Accepted: 17 December 2018 / Published: 20 December 2018
(This article belongs to the Special Issue σ and π Holes: A New Class of Non-Covalent Interactions)
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Abstract

Carbon bonding is a weak interaction, particularly when a neutral molecule acts as an electron donor. Thus, there is an interesting question of how to enhance carbon bonding. In this paper, we found that the –OCH3 group at the exocyclic carbon of fulvene can form a moderate carbon bond with NH3 with an interaction energy of about −10 kJ/mol. The –OSiH3 group engages in a stronger tetrel bond than does the –OGeH3 group, while a reverse result is found for both –OSiF3 and –OGeF3 groups. The abnormal order in the former is mainly due to the stronger orbital interaction in the –OSiH3 complex, which has a larger deformation energy. The cyano groups adjoined to the fulvene ring not only cause a change in the interaction type, from vdW interactions in the unsubstituted system of –OCF3 to carbon bonding, but also greatly strengthen tetrel bonding. The formation of tetrel bonding has an enhancing effect on the aromaticity of the fulvene ring. View Full-Text
Keywords: tetrel bonding; fulvene; substituents; aromaticity tetrel bonding; fulvene; substituents; aromaticity
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Hou, M.-C.; Yang, S.-B.; Li, Q.-Z.; Cheng, J.-B.; Li, H.-B.; Liu, S.-F. Tetrel Bond between 6-OTX3-Fulvene and NH3: Substituents and Aromaticity. Molecules 2019, 24, 10.

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