Citation: Wu Yile, Zhang Jie, Xie Zuowei. How long a C–C bond can be? An example of extraordinary long C-C single bond in 1, 2-diarylamino-o-carboranes[J]. Chinese Chemical Letters, ;2019, 30(8): 1530-1532. doi: 10.1016/j.cclet.2019.04.034 shu

How long a C–C bond can be? An example of extraordinary long C-C single bond in 1, 2-diarylamino-o-carboranes

Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Hong Kong, China

zxie@cuhk.edu.hk

Received Date: 15 February 2019
Revised Date: 1 April 2019
Accepted Date: 9 April 2019
Available Online: 17 August 2019

Figures(5)

How long a C-C bond can be? A question has long fascinated chemists. This work reports an example of extraordinary long C-C bond distance of 1.990(4) Å observed in single-crystal X-ray structure of 1, 2-(NHMes)₂-o-carborane (2; Mes=2, 4, 6-trimethylphenyl). DFT calculations show that hyperconjugation of lone pairs of the nitrogen atoms into the empty σ^* orbital of the cage C-C bond is the origin of the bond elongation. Such hyperconjugation can be suppressed if the two nitrogen atoms in 2 are linked to a Lewis acidic germanium (Ⅱ) center.
- o-Carborane,
- C–C single bond,
- Hyperconjugation,
- Amine,
- X-ray structure
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