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Structural Chemistry

, Volume 28, Issue 3, pp 823–831 | Cite as

Carbene tetrel-bonded complexes

  • Mingxiu Liu
  • Qingzhong Li
  • Wenzuo Li
  • Jianbo Cheng
Original Research

Abstract

An ab initio calculation has been carried for the carbene tetrel bonded complexes CH3Y∙∙∙CH2 (Y = F, CN, NC, and NO2), CH3F∙∙∙CZ2 (Z = Cl and CH3), XH3F∙∙∙CF2 (X = C, Si, Ge, and Sn), SiF4∙∙∙CF2, and XH3F∙∙∙NHC (N-heterocyclic carbene), where carbene is treated as a Lewis base and XH3Y is a Lewis acid. Formation of the tetrel bond is mainly attributed to charge transfer from the lone pair on the C atom in the carbene toward the σ* X–Y orbital and also the σ* X–H one in the strong tetrel bond. The carbene tetrel bond is strengthened/weakened by the electron-withdrawing group in the tetrel donor/acceptor and enhanced by the methyl group in C(CH3)2. NHC forms a stronger carbene tetrel bond in XH3F∙∙∙NHC (X = Si, Ge, and Sn) where it exceeds that of the majority of H-bonds. Interestingly, the tetrel bond becomes stronger in the order of X = C < Ge < Sn < Si in XH3F∙∙∙NHC and the largest interaction energy occurs in SiH3F∙∙∙NHC, amounting to −103 kJ/mol. The carbene tetrel bond can be strengthened by cooperative effect with the N∙∙∙M interaction in trimers H2C∙∙∙CH3CN∙∙∙M (M = CH3CN, HCN, ICN, SbH2F, LiCN, and BeH2) and has doubled in H2C∙∙∙CH3CN∙∙∙BeH2.

Keywords

Carbene Tetrel bonds Electrostatic interaction Cooperativity 

Notes

Acknowledgments

This work was supported by the National Natural Science Foundation of China (21573188) and the Graduate Innovation Foundation of Yantai University (YDZD1608).

Supplementary material

11224_2016_890_MOESM1_ESM.doc (5 mb)
ESM 1 (DOC 5149 kb)

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Mingxiu Liu
    • 1
  • Qingzhong Li
    • 1
  • Wenzuo Li
    • 1
  • Jianbo Cheng
    • 1
  1. 1.The Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical EngineeringYantai UniversityYantaiPeople’s Republic of China

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