
TY  - JOUR
A1  - Dyall, LK 
T1  - Solvent effects on the infrared spectra of anilines. VII. 2-Substituted 4-nitroanilines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1970
VL  - 23
IS  - 5
SP  - 947
EP  - 955
KW  - 
UR  - https://doi.org/10.1071/CH9700947 
N2  - 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. 
ER  -

