Tetrel Bond between 6-OTX<sub>3</sub>-Fulvene and NH<sub>3</sub>: Substituents and Aromaticity
Ming-Chang Hou,
Shu-Bin Yang,
Qing-Zhong Li,
Jian-Bo Cheng,
Hai-Bei Li,
Shu-Feng Liu
Affiliations
Ming-Chang Hou
The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
Shu-Bin Yang
The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
Qing-Zhong Li
The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
Jian-Bo Cheng
The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China
Hai-Bei Li
School of Ocean, Shandong University, Weihai 264209, China
Shu-Feng Liu
Shandong Key Laboratory of Biochemical Analysis, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
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.
