Blue-shifting C-H center dot center dot center dot O hydrogen bonded complexes between chloroform and three small cyclic ketones (cyclohexanone, cyclopentanone, and cyclobutanone) have been identified by use of FTIR spectroscopy in CC solution at room temperature. The shifts of the C-H stretching fundamental of chloroform (VC-H) in the said three complexes are +1, +2, and +5 cm(-1), respectively, and the complexation results in enhancement of the VC-H transition intensity in all three cases. The 1:1 stoichiometry of the complexes is suggested by identifying distinct isosbestic points between the carbonyl stretching (v(C=O)) fundamentals of the monomers and corresponding complexes for spectra measured with different chloroform to ketone concentrations. The v(C=O) bands in the three complexes are red-shifted by 8, 19, and 6 cm(-1), and apparently have no correlation with the respective blue shifts of the VC-H bands. Spectral analysis reveals that the complex with cyclohexanone is most stable, and the stability decreases with the ring size of the cyclic ketones. A qualitative explanation of the relative stabilities of the complexes is presented by correlating the hydrogen bond acceptor abilities of the carbonyl groups with the ring size of the cyclic ketones. Quantum mechanical calculations at the DFT/B3LYP/6-311++G(d,p) and MP2/6-31+G(d) levels were performed for predictions of the shapes of the complexes, electronic structure parameters of C-H (donor) and C=O (acceptor) groups, intermolecular interaction energies, spectral shifts, and evolution of those properties when the hydrogen bond distance between the donor-acceptor moieties is scanned. The results show that the binding energies of the complexes are correlated with the dipole moments, proton affinity, and n(O) - sigma*(C-H) hyperconjugative charge transfer abilities of the three ketones. NBO analysis reveals that the blue shifting of the VC-H transition in a complex is the net effect of hyperconjugation and repolarization/rehybridization of the bond under the influence of the electric field of carbonyl oxygen..