
%0 Journal Article
%A Dyall, LK 
%T Solvent effects on the infrared spectra of anilines. VII. 2-Substituted 4-nitroanilines
%J Australian Journal of Chemistry
%D 1970/05/01
%V 23
%N 5
%P 947-955
%K 
%R https://doi.org/10.1071/CH9700947
%U https://www.publish.csiro.au/paper/CH9700947 
%X Measurements of N-H stretching frequencies of 4-nitroanilines in the presence of hydrogen bond acceptors show that the ease of forming a second intermolecular hydrogen bond in the presence of an ortho substituent decreases in the order hydrogen > methyl > bromo, methoxyl > nitro. This order demonstrates the importance of repulsions between lone pair orbitals on the ortho substituent and the acceptor molecule. Weak intramolecular hydrogen bonds are detected in 2-iodo- and 2-bromo-aniline, and such bonds can be strengthened by introduction of a 4-nitro substituent. 
