Abstract

The intermolecular deuteron bonds formed between Cl<sub>3</sub>CD and ClCCl<sub>3</sub> are stronger than between Cl<sub>3</sub>CD and ClCCl<sub>2</sub>D, since the Cl atoms of CCl<sub>4</sub> are more basic than Cl atoms for CDCl<sub>3</sub>. The <i>n</i>-alkanes act as a diluent for CDCl<sub>3</sub> molecules, and the strength of the intermolecular proton bond in (Cl<sub>3</sub>CD:ClCCl<sub>2</sub>D)<sub><i>n</i></sub> complexes increases as <i>n</i> 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 CDCl<sub>3</sub>, 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 CDCl<sub>3</sub>. These conclusions are based on the study of the <i>v</i>CD, <i>v</i>C=C, and <i>v</i>(C=C)<sub>2</sub> frequencies vs. mole % CDCl<sub>3</sub> (or CHCl<sub>3</sub>)/solvent system.

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