The chiral discrimination energies in domains composed of chiral amphiphilic monolayers are theoretically studied. First, calculations on simpler model systems are carried out which show that the depth of the pair potential well is dependent on the extent of coarse-graining the molecular structure. However, systematic coarse-graining of model systems shows that the consistent use of a set of parameters can correctly predict the chiral preference (homo- or heterochirality). The model calculation further suggests that, with a gradual loss of chirality of the model molecule, the chiral interaction is diminished. Calculations of the chiral discriminating pair potential of three chiral compounds, N-stearoyl serine methyl ester, N-palmitoyl aspartic acid, and N-tetradecyl-gamma,delta-dihydroxypentanoic acid amide indicate homochiral preference. The preference is observed both in packing of a pair of molecules and the pair potential energy profile. The enantionteric pairs are closely packed and have a lower minimum pair potential compared to the racemic pairs. The homochiral preference corroborates well with the domain features observed by BAM. The growth in both directions observed in racemic domains are suggestive of local chiral symmetry breaking, which is possible in the case of the homochirally preferred interaction. We also compare the results of the calculation of discrimination energy by the present approach and the results by other molecular models available in the literature. Whereas the basic conclusions of the present model and other models agree, the present model reveals a nontrivial distance and orientation dependence of the discrimination energy. The results are insensitive to the choice of parameters.