The-NH, group in aniline is not completely planar with the benzene ring. Specifically, the angle to the benzene ring and the bisector of the amino group is 140° instead of 180°. By comparison, the analogous angle in methylamine is 125°, while in p-nitroaniline it is indeed 180°. H,C-N H HA H 140° 180 125 Aniline Methylamine p-Nitroaniline

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter27: Amino Acids And Proteins
Section: Chapter Questions
Problem 27.39P: A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug...
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In the structures of T—A and C—G base pairs, there are three amino groups specifically labeled as “sp2 hybridized and planar”. What is the primary
difference between these structures and that of
aniline that lead to their planarity?

1. In contrast to aniline, the amino groups on the DNA bases are necessary to make the heterocyclic rings aromatic.

2. In contrast to aniline, the contributing structures that delocalize the nitrogen lone pairs onto the rings creates partial negative charges on electronegative atoms.

3. In contrast to aniline, the hydrogen bond accepting ability of the lone pairs on the -NH2
groups of the DNA bases is better when these amino groups are sp2 hybridized.

4. Both 2 and 3.

The-NH, group in aniline is not completely planar
with the benzene ring. Specifically, the angle to the
benzene ring and the bisector of the amino group is
140° instead of 180°. By comparison, the analogous
angle in methylamine is 125°, while in p-nitroaniline it
is indeed 180°.
H,C-N
H
HA
H
140°
180
125
Aniline
Methylamine
p-Nitroaniline
Transcribed Image Text:The-NH, group in aniline is not completely planar with the benzene ring. Specifically, the angle to the benzene ring and the bisector of the amino group is 140° instead of 180°. By comparison, the analogous angle in methylamine is 125°, while in p-nitroaniline it is indeed 180°. H,C-N H HA H 140° 180 125 Aniline Methylamine p-Nitroaniline
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