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Proceedings Article | 5 July 2024 Paper

Effect of substitution group on intramolecular hydrogen bond of amino alcohols from Raman spectroscopy

Honghui Zhao, Hongyuan Shen, Ao You, Yuanqin Yu

Proceedings Volume 13183, 1318322 (2024) https://doi.org/10.1117/12.3033861

KEYWORDS: Hydrogen, Raman spectroscopy, Chemical species, Nitrogen, Molecules, Hydrogen energy, Electrons, Vibration, Molecular interactions, Carbon

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Due to the simultaneous presence of two polar functional groups and flexible spatial structure, Aminoethanol (AE) is a model system for investigating the relationship between intramolecular hydrogen bonding and conformational equlibrium. In addition, Aminoethanol and their derivatives exhibit remarkable efficacy in the reversible capture of carbon dioxide. The intramoleculr hydrogen bond of 2-AE is determined by a subtle balance between electrostatic interactions, Van der Waals interactions, and steric effects. Changing the polarity of functional groups can regulate the strength of intramolecular hydrogen bonds. In this work, using spontaneous Raman spectroscopy combined with theoretical calculations, we investigated the effect of N-terminated substitution group on intramolecular hydrogen bond. When the H atom of NH2 functional group is replaced by electron-donating groups such as methyl and ethyl, it was observed experimentally that the red-shift of OH stretching vibration frequency caused by O-H... N intramolecular hydrogen bonding increases significantly and then the corresponding peak intensity increases. This indicates that with the introduction of substitutions on the N atom, the O-H... N intramolecular hydrogen bond in 2-AE is enhanced and the corresponding conformational population increases. The results of AIM and NCI analysis are consistent with experimental observations. These results provide insights for regulating the strength of intramolecular hydrogen bonds and also contribute to the strategy of CO2 capture.

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