Many biological and environmental systems contain ion, water, and hydrophobic components; and it is the balance between these competing interactions which governs their chemistry. This Thesis aims at exploring ion•••hydrocarbon interactions, then ion•••water•••alkane interactions. To accomplish this, a combination of gas phase infrared predissociation spectroscopy (IRPD) and tandem mass spectrometry is utilized. The solvation of alkali metal ions by methane is discussed first, beginning with the effects of multiple argon atoms on Li+•••CH4 dimer clusters followed by a study of M+(CH4)n clusters where it is revealed that ions have a weak electrostatic effect beyond the first solvent shell.Next, the argon tagging and monitoring unique fragmentation channels are used to selectively probe for high energy Li+(H2O)3-4Ar1 conformers which contain extensive water hydrogen bonding. Finally, ion•••water•••alkane interactions are probed in Li+(H2O)n clusters containing CH4 or C6H12 molecules. Some spectra contain hydrogen bonded peaks correlating to weak water•••alkane interactions. Furthermore, there is strong evidence that high energy conformers containing water hydrogen bonding are present in the cluster ion beam. This analysis is expanded to anionic Cl-(Water)m(CH4)n clusters to compare with cations.Density functional theory or MP2 level calculations were used to support and help characterize experimental data.