We have previously mentioned that one of the best-known pro-CSA (Bz2oxP) suffers serious sensitivity issues due in part to N-alkylation. Additionally, the competitive binding of water molecules significantly contributes to the magnitude of splitting ∆σ. Trace amounts of water in solutions or titrants results in the necessary use of high guest concentrations to obtain well-resolved spectra. The hypersensitivity towards water is a major limitation for functional pro-CSA, since water is ubiquitous, avoiding it is at least tedious if not almost impossible for most of the solvents and reagents, especially for the analytes bearing high polarity. Hence, investigation of water influence as a competitive agent to the enantio-pure 22-Pꞏ10CSA(S) complex in CD3CN was carried out. From the first instance, the gradual addition of water has a considerable effect on ∆σ. By the addition of 240 eq. of water, the ∆σ of N-H has contracted by 0.132 ppm. (Figure ). Despite the competitive nature of water, the overall binding strength of 10CSA(S) remains observable considering the ~12.5 fold higher water consistency in the solution. Even at substantially higher (>4000 eq.) quantity of water the signals remained anisochronous highlighting the strong relationship between the host and chiral guest (Figure ).