Infrared Study of 4- and 3-Substituted Anilines in Hexane, Carbon Tetrachloride, or Chloroform (0.5% or less) Solutions

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As the NH2 bond angle increases, both v asym.NH2 and v sym.NH2 increase in frequency, and the frequency separation between v asym.NH2 and v sym.NH2 increases as the Hammett σ p and σ m values increase (increasing electron withdrawing power). The NH2 bond angles change with solute/solvent interaction. In CHCl3 solution IR bands are observed for two sets of v asym.NH2 and v sym.NH2 frequencies. It is suggested that this is the result of intermolecular hydrogen bonding between H2N and HCCl3 and between NH2 and Cl(HCl2)2. In CCl4 solution the intermolecular hydrogen bonding between the NH2 protons and the Cl atoms of CCl4 is stronger than between the Cl atoms of CHCl3.

Keywords: IR group frequencies for NH2; Infrared; Molecular structure; Solvent effects on NH2

Document Type: Research Article


Affiliations: Analytical Sciences Laboratory, 1897F Building, Dow Chemical Company, Midland, Michigan 48667

Publication date: August 1, 1992

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