Protons take part in many important reactions such as redox, acid-base chemistry and biochemistry; however, the mechanisms for proton transfer and hydronium’s stabilization are less understood. Hydronium sequestered in 18-crown-6 ether (CE) has an unusually broad and intense vibrational absorbance (OH-feature) compared to bare hydronium. One environmental factor affecting this OH-feature is the range of hydrogen bonded geometries between the hydrogen atoms in hydronium and the oxygen atoms in the CE, which is sampled by the complex even in its ground vibrational state. The breadth of the OH-feature is attributed to changes of the OH stretch frequency of hydronium as it rattles within the CE, and to the CE distorting to accommodate the hydronium. Hydronium will donate a proton to diethyl ether in the binary complex, because the diethyl ether is a stronger base than water. However, when hydronium hydrogen bonds to three diethyl ether molecules in a ternary complex, all three hydrogen atoms in hydronium are pulled by the ether molecules preventing any one of the protons from transferring. The hydrogen bonded geometries we analyze involve complexes of hydronium with both simple ethers and cyclic CE molecules. The CE hydrogen bonds to all three of the hydrogen atoms in hydronium similarly to the ternary complex, thus the CE complex prevents proton transfer. We explore several other environmental factors, including increasing the rigidity of the CE by replacing carbon-carbon single bonds with carbon-carbon double bonds. This increase in CE rigidity reduces the rattling of the hydronium. We also explore the effects of reducing electron density on the oxygen atoms in the CE by replacing hydrogen atoms in the CE with fluorine atoms. Optimizations, frequencies and potential energy scans are made at the B3LYP level of theory using a 6-311G(2d,p) basis.