Exceptionally Long C−C Single Bonds in Diamino‐<i>o</i>‐carborane as Induced by Negative Hyperconjugation

Junxia Li, Ronglin Pang, Zhifang Li, Guoqiao Lai, Xu‐Qiong Xiao, Thomas Müller

doi:10.1002/anie.201812555

Exceptionally Long C−C Single Bonds in Diamino‐<i>o</i>‐carborane as Induced by Negative Hyperconjugation

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Junxia Li

Hangzhou Normal University Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education No. 2318 Yuhangtang Rd. Hangzhou 311121 Zhejiang China
Ronglin Pang

Hangzhou Normal University Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education No. 2318 Yuhangtang Rd. Hangzhou 311121 Zhejiang China
Zhifang Li

Hangzhou Normal University Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education No. 2318 Yuhangtang Rd. Hangzhou 311121 Zhejiang China
Guoqiao Lai

Hangzhou Normal University Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education No. 2318 Yuhangtang Rd. Hangzhou 311121 Zhejiang China
Xu‐Qiong Xiao

Hangzhou Normal University Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education No. 2318 Yuhangtang Rd. Hangzhou 311121 Zhejiang China
Thomas Müller

Institut für Chemie Carl von Ossietzky Universität Oldenburg Carl-von-Ossietzky-Strasse 9–11 26129 Oldenburg Germany

書誌事項

公開日: 2018-12-07

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http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/anie.201812555

公開者: Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>The synthesis of a series of 1,2‐diamino‐<jats:italic>o</jats:italic>‐carboranes (<jats:bold>1</jats:bold>–<jats:bold>4</jats:bold>) is reported. The molecular structures of these diamino‐<jats:italic>o</jats:italic>‐carboranes are remarkable as the inner‐cluster C−C bonds are all ultra‐long (162.7–193.1 pm) and vary substantially with small variations in the substituents. The results of quantum mechanical investigations suggest that the origin of the bond elongation is significant in‐plane negative hyperconjugation of lone pairs of the nitrogen substituents with the σ* orbitals of the C−C bonds in <jats:italic>o</jats:italic>‐carboranes.</jats:p>