Competitive tetrel bond and hydrogen bond in benzaldehyde–CO 2 : characterization via rotational spectroscopy
2021 | journal article. A publication with affiliation to the University of Göttingen.
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Wang, H., Wang, X., Tian, X., Cheng, W., Zheng, Y., Obenchain, D. A., Xu, X. ... Gou, Q. (2021). Competitive tetrel bond and hydrogen bond in benzaldehyde–CO 2 : characterization via rotational spectroscopy. Physical Chemistry Chemical Physics, 23(45), 25784-25788. doi: https://doi.org/10.1039/D1CP03608D
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- Authors
- Wang, Hao; Wang, Xiujuan; Tian, Xiao; Cheng, Wanying; Zheng, Yang; Obenchain, Daniel A.; Xu, Xuefang; Gou, Qian
- Abstract
- The rotational spectrum of the 1 : 1 benzaldehyde–CO 2 complex has been investigated using pulsed-jet Fourier transform microwave spectroscopy complemented with quantum chemical calculations.
The rotational spectrum of the 1 : 1 benzaldehyde–CO 2 complex has been investigated using pulsed-jet Fourier transform microwave spectroscopy complemented with quantum chemical calculations. Two isomers, both characterized by one C⋯O tetrel bond (n → π interaction) and one C–H⋯O hydrogen bond (n → σ interaction), have been observed in the pulsed jet. Competition between the tetrel bond and the hydrogen bond has been disclosed by natural bond orbital analysis: isomer I is characterized by one dominating OC CO 2 ⋯O tetrel bond (12.6 kJ mol −1 ) and a secondary (C–H) formyl ⋯O hydrogen bond (2.2 kJ mol −1 ); by contrast, in isomer II the (C–H) phenyl ⋯O hydrogen bond (7.6 kJ mol −1 ) becomes the dominant bond, while the OC CO 2 ⋯O tetrel bond (5.8 kJ mol −1 ) becomes much weaker with respect to that of isomer I. Using intensity measurements the relative population ratio of the two isomers was estimated to be N I / N II ≈ 2/1.
The rotational spectrum of the 1 : 1 benzaldehyde–CO 2 complex has been investigated using pulsed-jet Fourier transform microwave spectroscopy complemented with quantum chemical calculations.
The rotational spectrum of the 1 : 1 benzaldehyde–CO 2 complex has been investigated using pulsed-jet Fourier transform microwave spectroscopy complemented with quantum chemical calculations. Two isomers, both characterized by one C⋯O tetrel bond (n → π interaction) and one C–H⋯O hydrogen bond (n → σ interaction), have been observed in the pulsed jet. Competition between the tetrel bond and the hydrogen bond has been disclosed by natural bond orbital analysis: isomer I is characterized by one dominating OC CO 2 ⋯O tetrel bond (12.6 kJ mol −1 ) and a secondary (C–H) formyl ⋯O hydrogen bond (2.2 kJ mol −1 ); by contrast, in isomer II the (C–H) phenyl ⋯O hydrogen bond (7.6 kJ mol −1 ) becomes the dominant bond, while the OC CO 2 ⋯O tetrel bond (5.8 kJ mol −1 ) becomes much weaker with respect to that of isomer I. Using intensity measurements the relative population ratio of the two isomers was estimated to be N I / N II ≈ 2/1. - Issue Date
- 2021
- Journal
- Physical Chemistry Chemical Physics
- ISSN
- 1463-9076
- eISSN
- 1463-9084
- Language
- English