Abstract

As the NH<sub>2</sub> bond angle increases, both <i>v</i><sub>asym.</sub>NH<sub>2</sub> and <i>v</i><sub>sym.</sub>NH<sub>2</sub> increase in frequency, and the frequency separation between <i>v</i><sub>asym.</sub>NH<sub>2</sub> and <i>v</i><sub>sym.</sub>NH<sub>2</sub> increases as the Hammett σ<sub><i>p</i></sub> and σ<sub><i>m</i></sub> values increase (increasing electron withdrawing power). The NH<sub>2</sub> bond angles change with solute/solvent interaction. In CHCl<sub>3</sub> solution IR bands are observed for two sets of <i>v</i><sub>asym.</sub>NH<sub>2</sub> and <i>v</i><sub>sym.</sub>NH<sub>2</sub> frequencies. It is suggested that this is the result of intermolecular hydrogen bonding between H<sub>2</sub>N and HCCl<sub>3</sub> and between NH<sub>2</sub> and Cl(HCl<sub>2</sub>)<sub>2</sub>. In CCl<sub>4</sub> solution the intermolecular hydrogen bonding between the NH<sub>2</sub> protons and the Cl atoms of CCl<sub>4</sub> is stronger than between the Cl atoms of CHCl<sub>3</sub>.

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