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

Yile Wu; Jie Zhang; Zuowei Xie

doi:10.1016/j.cclet.2019.04.034

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

Yile Wu
, Jie Zhang
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

17 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1530-1532
Number of pages	3
Journal	Chinese Chemical Letters
Volume	30
Issue number	8
DOIs	https://doi.org/10.1016/j.cclet.2019.04.034
Publication status	Published - Aug 2019

User-Defined Keywords

Amine
C–C single bond
Hyperconjugation
o-Carborane
X-ray structure

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.cclet.2019.04.034

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

abstract = "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) {\AA} 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.",

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author = "Yile Wu and Jie Zhang and Zuowei Xie",

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KW - Amine

KW - C–C single bond

KW - Hyperconjugation

KW - o-Carborane

KW - X-ray structure

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

Abstract

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