Nature of E–E bonds in heavier ditetrel alkyne analogues ArEEAr (Ar = C6H3-2,6(C6H3-2,6-Pri2)2; E = Si, Ge, Sn, and Pb)

Suhong Huo; Xiaoyan Li; Yanli Zeng; Zheng Sun; Shijun Zheng; Lingpeng Meng

doi:10.1039/C3NJ00600J

Nature of E–E bonds in heavier ditetrel alkyne analogues ArEEAr (Ar = C₆H₃-2,6(C₆H₃-2,6-Prⁱ₂)₂; E = Si, Ge, Sn, and Pb)†

Suhong Huo,^ab Xiaoyan Li,*^a Yanli Zeng,^a Zheng Sun,^a Shijun Zheng^b and Lingpeng Meng*^a

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* Corresponding authors

^a College of Chemistry and Material Science, Hebei Normal University, Road East of 2nd Ring South, Shijiazhuang, China

^b College of Chemical and Materials Engineering, Yanching Institute of Technology, Road North of Yingbin, Yanjiao National High-tech Industry Development Zone, China
E-mail: lixiaoyan326@163.com, menglp@hebtu.edu.cn
Tel: +86 311 80787427

Abstract

The nature of the E–E bonds in heavier ditetrel alkyne analogues ArEEAr (Ar = C₆H₃-2,6(C₆H₃-2,6-Prⁱ₂)₂; E = Si, Ge, Sn, Pb) have been studied by topological analysis of the electron localization function (ELF), the delocalization index from the atoms in molecules (AIM) theory and bond orbital analysis. Both the topological and the orbital analysis show that the nature of the E–E bonds in ArEEAr are different to that of the classical covalent triple C [triple bond, length as m-dash] C bond of ArCCAr. In ArEEAr, all of the E–E bonds display charge-shift character; the ELF valence basin centroids of the E–E (E = Ge, Sn) bond do not occupy the central region between the two atoms, but have, in effect, fled that region and split into two kinds of basins. In addition, more and more electrons are transferred from the bond basins of the E–E bond to the lone pair basin of the E atoms, which means that a great portion of the bonding components comes from the lp (lone-pair) orbitals of the E atom rather than the electron-sharing bond, as in acetylene. Furthermore, the strength of the E–E bond decreases in the sequence of E = Si, Ge, Sn, and Pb.

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Article information

DOI: https://doi.org/10.1039/C3NJ00600J
Article type: Paper
Submitted: 06 Jun 2013
Accepted: 17 Jul 2013
First published: 19 Jul 2013

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New J. Chem., 2013,37, 3145-3151

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Nature of E–E bonds in heavier ditetrel alkyne analogues ArEEAr (Ar = C₆H₃-2,6(C₆H₃-2,6-Prⁱ₂)₂; E = Si, Ge, Sn, and Pb)

S. Huo, X. Li, Y. Zeng, Z. Sun, S. Zheng and L. Meng, New J. Chem., 2013, 37, 3145 DOI: 10.1039/C3NJ00600J

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