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In order to investigate ring-size effects on the stability and spectral shifts of hydrogen bonded cyclic ethers complexes, the strength of hydrogen bonds in gas phase complexes formed between 2,2,2-trifluoroethanol (TFE) and selected cyclic ethers were examined using FTIR spectroscopy. TFE was chosen as hydrogen bond donor in these complexes, while trimethylene oxide (TMO), tetrahydrofuran (THF) and tetrahydropyran (THP) were selected as hydrogen bond acceptors. Comparable OH-stretching red shifts were observed in the three kinds of complexes. The difference of red shifts is so small (<7 cm −1 ) for TFE−TMO/THF/THP complexes that one can conclude that their stabilities and the strength of the hydrogen bonds are nearly similar and do not show any marked dependence with the ring size of the hydrogen bond acceptor. The equilibrium constants for the complexation were determined, and atoms-in-molecules (AIM) and natural bond orbital (NBO) analyses were performed to further investigate the intermolecular interactions. Regardless of the ring size, hydrogen bonds in the complexes showed similar strength, in agreement with the observed OH-stretching red shifts.

Ring-Size Effects on the Stability and Spectral Shifts of Hydrogen Bonded Cyclic Ethers Complexes