54
The Chemical Origins of Biology
2.19
*2.14
Table 1
K
A
B
C
D
E
F
G
H
3
2
*A
3
2
NH4+
AcO-
+
+
NH3
AcOH
p Ka 9.3
2 2
p Ka 4.7
3 2
B
3
NH2+
+
H2N
NH2
pKa 13.6
2.15
A
3
C
B
NH
NH3
H2 N
NH4+
+
NH2
pKa 9.3
O
+
3
O-
HO -
H2O
+
pKa 20
*2.16
n
π
A
B
C
O
*2.20
D
O
O
O
pKa 15.7
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H3 C
N
.. CH2
N
C
C
H
NH2
Me
N
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©*2.17
HO
OH
O
HO
A
B
H
C
N
C
C
C
H
H
- ..
N
..
N
H2 N
+
N
H
O
O
N+
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*2.18
O
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*2.21
A
B
H HN
K
Kʹ
Kʹ
K
C
nipecotic acid derivative
anticonvulsant
pinnaic acid
inhibitor of phospholipase A2
O
+
+
HO
N
HN
A
Cl
OH
O
N
A
A
O
Ph
Ph
B
1 M HCl
O
OCH3
OCH3
1 M HCl
HO
2
100 ˚ C
H2O
100 ˚ C
O
Ph
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nipecotic
acid derivative design byquinine
OH
pinnaic acid
Ph inhibitor
OH of phospholipase A2
antimalarial
anticonvulsant
O
B
B
O
OH
0.1 M NaOH
HO
OMe
O
OH
HN
O
OH
0.1 M NaOH
Cl
H2O
25 ˚ C
H2O
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O
OH
O
OH
O
N
OH
N
O
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N
OH
O
OH
OH
N
55
Table 1
1. Electronegativity
2. Hybridization
50
H3C NH3+ 10
H3C NH2 ~36
H2C NH2+ ~5
H3C CH3
HC NH+
16
H3C OH
4. Charge
HO H
+
H2O H
H
H3CO H
+
O
-10
3. Resonance
O
41
CH3
NH2
O
~28
O
10
OH
CH3
NH2
5. Row
16
H3CO H 16
-2
H3CS H
9
F H
3
-4
Br
~20
OH
OH+
5
~17
OH
-6
5
OH
H -8
Cl
NH3+ 5
H -9
O
- O P O H 12
-O
O
HO P O H 7
-O
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2.22
2.26
*A
G
B
O
H
N
N
H
O
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©2.27
+
ΔG = –9.8 kcal mol–1 at 25 ˚C
*2.28
2.23
*2.24
ribose
O
OH
αD
α-D-ribopyranose
NH2
O
HO
HO
OH
-O
HO
O
O
P
O
HO
O
NH3 +
CO2 -
*2.30
β-D-ribopyranose
O
OH
N
H
HO
O-
O
A o
B
C
D
E
OH
HO
HO
OH
2.25
ribofuranose
OH
O
O
C
HO
OH
HO
3N
OH
HO
+H
H
N
O
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2.29
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B
HO
anomeric center
HO
H
OH
A
pH 6
OH
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A
B
D
2.31
NH3
N C C N
cyanogen
H2N C N
aminonitrile
+
HCN
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56
The Chemical Origins of Biology
2.32
*2.33
NH3
H2N C N
2.34
NH
H 2N
guanidine
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O
H2O
H2N C N
2.35
NH2
pH 6
H2N
NH2
urea
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2.36
+H
3N
O
CN-
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