The intermolecular deuteron bonds formed between Cl3CD and ClCCl3 are stronger than between Cl3CD and ClCCl2D, since the Cl atoms of CCl4 are more basic than Cl atoms for CDCl3. The n-alkanes act as a diluent for CDCl3 molecules, and the strength of the intermolecular proton bond in (Cl3CD:ClCCl2D)n complexes increases as n becomes larger. Solvent density also plays an important role in solute/solvent interaction. Increased solvent density causes the CD:Cl or CD:π (of C=C group) intermolecular bond distance to decrease, causing the bond to be stronger. A repulsion exists between the intermolecular π electron system of benzene, 1,3-cyclohexadiene, or 1,4-cyclohexadiene and the chlorine atom σ electrons of CDCl3, and this repulsive effect is a factor in establishing the equilibrium intermolecular bond distance formed between the CD:π bonds of benzene (or cyclohexadienes) and the proton of CDCl3. These conclusions are based on the study of the vCD, vC=C, and v(C=C)2 frequencies vs. mole % CDCl3 (or CHCl3)/solvent system.
R. A. Nyquist, "Infrared Study of Solute/Solvent Interactions Between Separate Chloroform Solutions of Alkanes, Cycloalkanes, Alkenes, Cycloalkenes, Cyclohexadienes, Benzene, and Carbon Tetrachloride," Appl. Spectrosc. 47, 560-565 (1993)