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Pressure-Induced Hydrogen Transfer in 2‑Butyne via a Double CH···π Aromatic Transition State

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journal contribution
posted on 04.05.2022, 19:11 authored by Peijie Zhang, Xingyu Tang, Chunfang Zhang, Dexiang Gao, Xuan Wang, Yajie Wang, Wenhan Guo, Ruqiang Zou, Yehua Han, Xiaohuan Lin, Xiao Dong, Kuo Li, Haiyan Zheng, Ho-kwang Mao
Hydrogen transfer (H-transfer) is an important elementary reaction in chemistry and bioscience. It is often facilitated by the hydrogen bonds between the H-donor and acceptor. Here, at room temperature and high pressure, we found that solid 2-butyne experienced a concerted two-in–two-out intermolecular CH···π H-transfer, which initiated the subsequent polymerization. Such double H-transfer goes through an aromatic Hückel six-membered ring intermediate state via intermolecular CH···π interactions enhanced by external pressure. Our work shows that H-transfer can occur via the CH···π route in appropriate conformations under high pressure, which gives important insights into the H-transfer in solid-state hydrocarbons.