Solvent effects on the infrared spectra of anilines. VII. 2-Substituted 4-nitroanilines
Keyword(s):
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.
2018 ◽
2002 ◽
Vol 2002
(5)
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pp. 840-855
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2018 ◽
2016 ◽
Vol 72
(2)
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pp. 139-142
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1967 ◽
Vol 45
(19)
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pp. 2135-2141
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2020 ◽
Vol 20
(4)
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pp. 362-371
1959 ◽
Vol 55
(0)
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pp. 220-224
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