N
X
C
Hal
O
N
S
P Si
Natural
Products
Solvents
C
C
C
C C
C
4.13 Natural Products
153
+
H 3 N
OH
O
OH
+
H 3 N
OH
O
OH
O
+
H 3 N
O
–
O
OH
O
H 2 N
O
–
O
O
O
–
+
H 3 N
OH
O
O
OH
+
H 3 N
O
–
O
O
OH
H 2 N
O
–
O
O
O
–
+
H 3 N
O
–
O
+
H 3 N
O
–
O
OH
(in D 2 O/DCl)
H 2 N
O
–
O
H 2 N
H 2 N
O
–
O
+
H 3 N
+
H 3 N
OH
O
+
H 3 N
+
H 3 N
OH
O
NH 3
+
H 2 N
O
–
O
NH 2
H 2 N
O
–
O
NH 3
+
136.0
127.8
128.2
128.5
155.8
157.7
130.0
116.8
118.6
130.2
131.7
133.5
37.2
36.4
37.3
56.9
57.1
56.7
174.7
174.9
173.8
35.0
26.1
28.1
30.5
30.7
24.0
22.6
34.7
24.0
22.6
35.3
29.4
23.6
37.8
28.2
28.7
31.2
44.5
33.0
33.3
35.7
50.6
53.4
53.7
54.0
53.5
56.0
55.5
55.9
55.3
57.2
57.2
57.3
172.0
172.6
172.8
173.2
175.5
175.8
175.3
175.8
183.4
183.9
184.6
184.6
174.4
172.4
40.2
27.6
40.5
178.7
182.4
40.3
27.7
40.5
181.3
184.0
41.9
33.0
41.8
(pH 0.41)
(pH 0.32)
(pH 0.46)
(pH 0.50)
(pH 6.73)
(pH 6.95)
(pH 5.02)
(pH 6.03)
(pH 12.73)
(pH 12.51)
(pH 13.53)
(pH 13.85)