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PKA List Table
33
pKa Data Compiled by R. Williams page-1 pKa Values INDEX Inorganic 2 Phenazine 24 Phosphates 3 Pyridine 25 Carboxylic acids 4, 8 Pyrazine 26 Aliphatic 4, 8 Aromatic 7, 8 Quinoline 27 Phenols 9 Quinazoline 27 Alcohols and oxygen acids 10, 11 Quinoxaline 27 Amino Acids 12 Special Nitrogen Compounds 28 Peptides 13 Hydroxylamines 28 Nitrogen Compounds 14 Hydrazines 28 Aliphatic amines 15, 17, 19 Semicarbazones 28 Cyanoamines 16 Amidoximes 28 Anilines 17, 18, 20 Thiols 29 Nucleosides 21 Carbon Acids 30,31 Special Table Heterocycles 22 Indicators 31 Acridine 23 References 32-34 Benzoquinoline 24 Cinnoline 23 Hydantoin 24 Imidazole 24 For complex chelating agents, see also reference 77. Note. This document was compiled by W.P. Jencks and has been added to by F.H. Westheimer
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Transcript of PKA List Table
pKa Data Compiled by R. Williams page-1
pKa Values
INDEX
Inorganic 2 Phenazine 24
Phosphates 3 Pyridine 25
Carboxylic acids 4, 8 Pyrazine 26
Aliphatic 4, 8
Aromatic 7, 8 Quinoline 27
Phenols 9 Quinazoline 27
Alcohols and oxygen acids 10, 11 Quinoxaline 27
Amino Acids 12 Special Nitrogen Compounds 28
Peptides 13 Hydroxylamines 28
Nitrogen Compounds 14 Hydrazines 28
Aliphatic amines 15, 17, 19 Semicarbazones 28
Cyanoamines 16 Amidoximes 28
Anilines 17, 18, 20 Thiols 29
Nucleosides 21 Carbon Acids 30,31
Special Table Heterocycles 22 Indicators 31
Acridine 23 References 32-34
Benzoquinoline 24
Cinnoline 23
Hydantoin 24
Imidazole 24
For complex chelating agents, see also reference 77.
Note. This document was compiled by W.P. Jencks and has been added to by F.H. Westheimer
pK
a D
ata
Com
pile
d b
y R
. Will
iam
sp
age-
2
AC
IDS
Com
pou
nd
pK
Ref
.H
3PO
22.
0, 2
.23*
28H
2PO
4–7.
21*
77A
gOH
3.96
4H
PO4_
12.3
2*77
Al(
OH
) 311
.228
H3P
O3
2.0
28A
s(O
H) 3
9.22
28H
2PO
3–6.
58*
77H
3AsO
42.
22, 7
.0, 1
3.0
28H
4P2O
71.
52*
77H
2AsO
4–6.
98*
77H
3 P
2O7–
2.36
*77
HA
sO4*
11.5
3*77
H2P
2O7=
6.60
*77
As 2
O3
04
HP
2O7=
9.25
*77
H3A
sO3
9.22
*H
3BO
39.
23*
28H
ReO
4-1
.25
30H
2B4O
74.
0034
HSC
N4.
0034
H2S
eO3
2.6,
8.3
, 2.6
2*28
HB
4O7
9.00
34H
SeO
38.
3277
Be(
OH
) 23.
74
H2S
eO4
Stro
ng, 2
.028
HB
r-9
.00
31H
OB
r8.
728
HSe
O4
2.00
34H
OC
l7.
53, 7
.46
28, 3
3H
3SiO
310
.034
HC
lO2
2.0
28H
2SO
31.
9, 7
.0, 1
.76*
28, 7
7H
ClO
3-1
.00
28H
2SO
4-3
.0, 1
.928
HC
lO4
(70%
)-1
0.00
31H
SO3
7.21
*77
CH
3SO
3H-0
.631
HSO
4–1.
99*
77H
CN
9.40
34H
2S2O
41.
929
H2C
O3
6.37
, 6.3
5*, 3
.58
34, 3
2H
2Se
3.89
*77
HC
O3
10.3
3*H
Se–
11.0
0*77
H2C
rO4
-0.9
830
H2S
7.00
*77
HC
rO4
6.50
*2,
30
HS–
12.9
2*77
HO
CN
3.92
34H
SbO
211
.034
HZ
3.17
*, 0
.59*
77H
Te
5.00
34H
2GeO
38.
59, 1
2.72
34, 7
8H
2Te
2.64
, 11.
034
, 78
Ge(
OH
) 48.
68, 1
2.7
28H
2TeO
32.
7, 8
.028
HI
-10.
031
Te(
OH
) 66.
2, 8
.828
HO
I11
.028
H2V
O4–
8.95
30H
IO3
0.8
28H
VO
4=14
.430
H4I
O6–
6.00
34H
2CrO
40.
7477
H5I
O6
1.64
, 1.5
5, 8
.27
34, 2
8H
OC
N3.
7377
HM
nO4
-2.2
530
HSC
N0.
8577
NH
3OH
*5.
98*
H3P
O2
1.07
77N
H4*
9.24
*77
H3P
O4
2.12
*77
HN
34.
72*
77H
2S2O
30.
60*,
1.7
2*77
HN
O2
3.29
28H
3AuO
313
.3, 1
6.0
78H
NO
3-1
.328
H3G
aO3
10.3
2, 1
1.7
78N
2H5+
7.99
*77
H5I
O6
3.29
, 6.7
0, 1
5.0
78H
2N2O
27.
0534
(see
abo
ve!)
H2N
2O2–
11.0
34H
4V6O
171.
9678
H2O
sO5
12.1
34H
2NSO
3H1.
080
H2O
15.7
none
H3O
+-1
.7no
ne*
Indi
cate
s a
ther
mod
ynam
ic v
alue
.P
b(O
H) 2
6.48
(10
.92)
4 (7
8)
PH
OSP
HA
TE
S A
ND
PH
OSP
HO
NA
TE
SC
F 3-
1.16
, 3.9
357
CC
l 3-
1.63
, 4.8
157
Ph
osp
hat
esN
H3+ C
H2-
2.35
, 5.9
57C
ompo
und
pK
Ref
.(–
OO
CC
H2)
2NH
+ CH
2–--
, 5.5
757
Ph
osp
hat
e1.
97, 6
.82,
12.
555
CH
Cl 2
-1.
14, 5
.61
57G
lyce
ric
acid
2-p
hosp
hate
3.6
, 7.1
53C
H2C
I-1.
40, 6
.30
57E
nolp
yru
vic
acid
3.5,
6.4
53C
H2B
r-1.
14, 6
.52
57M
eth
yl-
1.54
, 6.3
155
(–O
OC
CH
22N
H+ (
CH
2)2-
--
, 6.5
457
Eth
yl-
1.60
, 6.6
255
CH
2I-
1.30
, 6.7
257
n-P
rop
yl-
1.88
,6.6
755
NH
3+ CH
2CH
2-2.
45, 7
.00
57n
-Bu
tyl-
1.80
, 6.8
455
Dim
eth
yl-
1.29
55C
6H5C
H=
CH
-2.
00, 7
.157
Di-
n-p
rop
yl1.
5955
HO
CH
2-1.
91, 7
.15
57D
i-n
-bu
tyl-
1.72
55C
6H5N
H2+
(CH
2)3-
2.1,
--
57G
luco
se-3
-0.
84, 5
.67
56C
6H5N
H(C
H2)
3---
, 7.1
757
Glu
cose
-4-
0.84
, 5.6
756
Br(
CH
2)2-
2.25
, 7.3
57α
-gly
cero
-1.
40, 6
.44
54C
H3(
CH
2)5C
H(C
OO
–)-
--, 7
.557
β-gl
ycer
o-1.
37, 6
.34
54C
6H5C
H2-
2.3,
7.5
557
3-p
hosp
hogl
ycer
ic a
cid
1.
42, 3
.42
54N
H3+ (
CH
2)4)
-2.
55, 7
.55
572-
pho
spho
glyc
eric
aci
d 1
.42,
3.5
5, 7
.1pe
roxy
mon
opho
spho
ric
acid
4.0
569
NH
3+ (C
H2)
5-2.
6, 7
.657
dip
hosp
hogl
ycer
ic a
cid
7.
40, 7
.99
54N
H3+ (
CH
2)10
---
, 8.0
057
glyc
eral
deh
yde-
2.10
, 6.7
554
– OO
C(C
H2)
10-
--, 8
.25
57d
ioxy
acet
one-
1.77
,6.4
554
(CH
3)3S
iCH
2-3.
22, 8
.70
57he
xose
di-
1.52
, 6.3
154
fruc
tose
-6-
0.97
, 6.1
154
C6H
5CH
2-3.
3, 8
.457
gluc
ose-
6-0.
94, 6
.11
54(C
6H5)
SC-
3.85
, 9.0
057
gluc
ose-
1-1.
10, 6
.13
54ad
enyl
ic a
cid
3.8?
, 6.2
?54
Ary
lph
osp
hon
ic a
cid
sin
osin
ic a
cid
2.4?
, 6.4
?54
2X-R
C6H
3PO
3H2
AD
P2
stro
ng, 6
.654
XR
AT
P3
stro
ng, 6
.654
Cl
4-O
2N1.
12, 6
.14
57p
yrop
hosp
hori
c ac
id0.
9, 2
.0, 6
.6, 9
.454
Br
5-O
2N(a
), 6
.14
57p
hosp
hop
yru
vic
acid
3.5,
6.3
854
Cl
5-C
l(a
), 6
.63
57cr
eati
ne
ph
osp
hat
e2.
7, 4
.554
Cl
H1.
63, 6
.98
57ar
gin
ine
ph
osp
hat
e2.
8, 4
.5, 9
.6, 1
1.2
54B
rH
1.64
, 7.0
057
argi
nine
2.02
, 9.0
, 12.
554
Br
5-C
H3
1.81
, 7.1
557
amin
o p
hosp
hate
(-0.
9), 2
.8, 8
.254
Cl
4-N
H2
--, 7
.33
57tr
imet
aph
osp
hat
e2.
0577
CH
3O4-
O2N
1.53
, 6.9
657
CH
3OH
2.16
, 7.7
757
Ph
osp
hon
ates
CH
3O4-
O2N
--, 8
.22
57H
2O3P
(CH
2)4P
O3H
2 <
2, 2
.75,
7.5
4, 8
.38
57H
O4-
O2N
1.22
, 5.3
957
H2O
3P(C
H2)
3PO
3H2
<2,
2.6
5, 7
.34,
8.3
557
O2N
H1.
45, 6
.74
57H
2O3P
CH
2CH
(CH
3)PO
3H2
<2,
2.6
, 7.0
0, 9
.27
57F
H1.
64, 6
.80
57H
2O3P
CH
2PO
3H2
<2,
2.5
7, 6
.87,
10.
3357
IH
1.74
, 7.0
657
Met
hy
l-2.
3557
NH
2H--
, 7.2
957
Eth
yl-
2.43
57C
H3H
2.10
, 7.6
857
n-p
rop
yl-
2.45
57C
6H5
H(a
), 8
.13
57is
opro
pyl
-2.
55, 7
.75
57H
OO
CH
1.71
, 9.1
757
n-bu
tyl-
2.59
, 8.1
957
isob
uty
l-2.
70, 8
.43
57**
The
se v
alu
es w
ere
obta
ined
in 5
0% e
than
ol.
s-bu
tyl-
2.74
, 8.4
857
(a) T
he c
ompo
und
s w
ere
not s
uffi
cien
tly
solu
ble.
t-bu
tyl-
2.79
, 8.8
857
For
grap
hica
l pl
ots
of a
lar
ge n
umbe
r of
sub
stit
uted
phos
phor
us c
ompo
unds
see
83.
neop
enty
l-2.
84, 8
.65
571,
1 D
imet
hyl
pro
pyl
-2.
88, 8
.96
57n
-hex
yl-
2.6,
7.9
57tr
iph
osp
hat
e8.
90, 6
.26,
2.3
077
n-d
odec
yl-
--, 8
.25
57te
tram
etap
hos
ph
ate
2.74
77C
H3(
CH
2)5C
H(C
OO
H)-
1, -
-57
flu
orop
hosp
hate
0.55
, 4.8
56A
ceti
c ac
ids,
su
bst
itu
ted
Ph
osp
hon
ates
(Ref
. 2)
H-
4.76
*20
X-H
-H-N
H3+
-NH
3+O
2N-
1.68
*20
X(C
H2)
PO3H
22.
357.
11.
855.
35(C
H3)
3N+ -
1.83
*20
X(C
H2)
2PO
3H2
2.45
7.85
2.45
7.00
(CH
3)2N
H+ -
1.95
*20
X(C
H2)
4PO
3H2
2.55
7.55
CH
3NH
2+ -2.
16*
20X
(CH
2)5P
O3
H2
2.6
7.65
NH
3+ -2.
31*
20X
(CH
2)6P
O2H
22.
67.
9C
H3S
O2-
2.36
*20
X(C
H2)
10PO
2H2
8.00
NC
-2.
43*
20P
hosp
hine
s in
ace
toni
tril
e, s
ee r
ef. 8
9.C
6H5S
O2-
2.44
20H
O2C
2.83
*20
CA
RB
OX
YL
IC A
CID
SA
lip
hat
icC
6H5S
O-
2.66
20C
ompo
und
pK
Ref
.F-
2.66
20A
ceto
acet
ic3.
586
Cl-
2.86
*20
Ace
topy
ruvi
c2.
61, 7
.85
(eno
l)6
Br-
2.86
20A
coni
tic,
tran
s-2.
80, 4
.46
6C
l 2-
1.29
20B
etai
ne1.
846
F 2-
1.24
20C
itri
c3.
09, 4
.75,
5.4
16
Br 3
-0.
6620
Cro
toni
c4.
696
Cl 3
-0.
6520
Dih
ydro
xyfu
mar
ic1.
146
F 3-
0.23
(-0.
26) (
2)20
Det
hyle
ned
iam
ine-
2.00
, 2.6
76
HO
NC
43.
0120
tetr
aace
tic
6.16
, 10.
26F 3
C-
3.07
*20
Form
ic3.
77*
2N
3-3.
0320
Fum
aric
3.03
, 4.5
46
I-3.
1220
Gly
ceri
c3.
556
C6H
5O-
3.12
20G
lyco
llic
3.82
6C
2H5O
2C-
3.35
20G
lyox
ylic
3.32
6C
6H5S
-3.
52*
20H
omog
enti
stic
4.40
6C
H3O
-3.
5320
α-k
eto-β-
met
hyl v
aler
ic 2
.36
NC
S-3.
5820
Lact
ic3.
866
CH
3CO
-3.
58*
20M
alei
c1.
93, 6
.58
6M
alic
3.40
, 5.2
6C
2H5O
-3.
6020
Oxa
loac
etic
(tra
ns-e
nol)
2.5
66
n-C
3H7O
3.65
20+
(cis
-eno
l)2.
15, 4
.06
6n-
C4H
9O3.
6620
Prot
ocat
echu
ic4.
486
sec.
-C4H
9O-
3.67
20Py
ruvi
c2.
506
HS-
3.67
*20
Tar
tari
c +
2.99
, 4.4
06
i-C
3H7O
-3.
69*
20+
or
-2.
89, 4
.40
6C
H3S
-3.
72*
20m
eso
3.22
, 4.8
56
i-C
3H7S
-3.
72*
20V
inyl
acet
ic4.
426
C6H
5CH
2S-
3.73
*20
C2H
5S-
3.74
*20
n-C
3H7S
-3.
77*
20n-
C4H
9S-
3.81
*20
HO
-3.
83*
20– O
3S-
4.05
20(C
6H5)
3CS-
4.30
*20
C6H
5-4.
31*
20C
H2-
CH
-4.
35*
20
* In
dica
tes
ther
mod
ynam
ic v
alue
s.
Un
satu
rate
d a
cid
s (2
5°)
Com
poun
dp
Kre
f.C
ompo
und
pK
ref.
tran
s-C
H3-
CH
=C
HC
O2H
4.69
*20
H-C
H2C
H2C
O2H
4.88
*2
cis-
CH
3-C
H=
CH
CO
2H4.
44*
2H
-CH
=C
HC
O2H
4.25
*2
C6H
5-C
H2C
H2C
O2H
4.66
*2
C6H
5CH
2CH
2CO
2H4.
66*
2tr
ans-
C6H
5-C
H=
CH
CO
2H4.
44*
2C
6H5C
H=
CH
CO
2H**
4.44
*2
m-C
H3O
C6H
4CH
2CH
2CO
2H4.
65*
2C
6H5C
H2C
H2C
O2H
4.66
*2
C6H
5CH
=C
HC
O2H
**4.
442
m-C
H3O
C6H
4CH
=C
HC
O2H
4.38
*2
m-C
lC6H
4CH
=C
HC
O2H
**4.
29*
2m
-ClC
6H4C
H2C
H2C
O2H
4.58
*2
Un
satu
rate
d a
cid
s, C
is-
and
Tra
ns-
CC
R2
H R1
CO
2H
CC
R2
R1 H
CO
2H
Cis
-Aci
dTr
ans-
Acid
R1
R2
cis-
acid
tran
s-ac
idR
ef.
H-
H-
4.25
*4.
25*
2C
H3-
H-
4.44
*4.
69*
2C
l-H
-3.
323.
652
C6H
5-H
-3.
88*
4.44
*2
ClC
6H4
H-
3.91
4.41
26-
BrC
6H4
H-
4.02
4.41
2C
H3-
CH
3-4.
305.
022
C6H
5-H
-5.
26**
*5.
58**
*2
2,4,
6-(C
H3)
3C6H
2-H
-6.
12**
*5.
70**
*2
C6H
5-C
H3-
4.98
***
5.98
***
2D
icar
box
ylic
aci
ds,
un
satu
rate
d*
Mal
eic
1.92
, 6.2
32
Ali
cycl
ic D
icar
box
ylic
aci
ds
Citr
acon
ic (D
imet
hylm
alei
c ac
id)
2.29
, 6.1
52
cis-
Car
onic
(1,1
-dim
ethy
lcyc
lopr
opan
e-23
-di
carb
oxyl
ic a
cid
2.34
*, 8
.31*
2A
cety
lene
dic
arbo
xylic
1.73
, 4.4
02
Δ1-t
etra
hyd
roph
thal
ic3.
01, 5
.34
21,
2-tr
ans-
cycl
opro
pane
dic
arbo
xylic
3.65
*, 5
.13*
2B
rom
omal
eic
1.45
, 4.6
22
tran
s-ca
roni
c3.
82*,
5.3
2*2
Bro
mof
umar
ic1.
46, 3
.57
21,
2-ci
s-cy
clop
ropa
ne-d
icar
boxy
lic3.
33*,
6.4
7*2
Chl
orof
umar
ic1.
78, 3
.81
2Fu
mar
ic3.
02, 4
.38
2M
esac
onic
(Dim
ethy
lfum
aric
aci
d)**
tran
s3.
09, 4
.75
2**
*in
40%
ace
tone
Phth
alic
2.95
, 5.4
12
*the
rmod
ynam
icIt
acon
ic (1
-Pro
pene
-2-3
-dic
arbo
xylic
aci
d)
3.85
, 5.4
52
Chl
orom
alei
c1.
72, 3
.86
2
Ali
ph
atic
Alic
yclic
Dic
arbo
xylic
aci
ds
Com
pou
nd
pK
Ref
Com
pou
nd
pK
Ref
1,2-
tran
s-C
yclo
pro
pan
e-ci
s-E
thyl
eneo
xid
e-d
icar
boxy
lic3.
65, 5
.13
2d
icar
boxy
lic1.
94,
3.92
2tr
ans-
Eth
ylen
eoxi
de-
1,3-
cis-
Cyc
lobu
tane
-d
icar
boxy
lic1.
93,
3.25
2d
icar
boxy
lic4.
03, 5
.31
21,
3-tr
ans
-Cyc
lobu
tane
di-
1,2-
cis-
Cyc
lop
enta
ne-
carb
oxyl
ic3.
81,
5.28
2d
icar
boxy
lic4.
37,
6.51
21,
2-tr
ans-
Cyy
clop
enta
ne-
1,3-
cis-
Cyc
lop
enta
ned
icar
boxy
lic3.
89, 5
.91
2d
icar
boxy
lic4.
23, 5
.53
21,
3-tr
ans-
Cyc
lop
enta
ne-
1,2-
cisC
yclo
hexa
ne-
dic
arbo
xylic
4.40
, 5.4
52
dic
arbo
xylic
4.34
, 6.7
62
1,2-
tran
s-C
yclo
hexa
ne-
1,3
-cis
-Cyc
lohe
xane
-d
icar
boxy
lic4.
18, 5
.93
2d
icar
boxy
lic4.
10, 5
.46
21,
3-tr
ans-
Cyc
lohe
xane
-1,
4-ci
s-C
yclo
hexa
ned
icar
boxy
lic4.
31, 5
.73
2d
i-ca
rbox
ylic
4.44
, 5.7
92
1,4-
tran
s-C
yclo
hexa
ne-
dic
arbo
xylic
4.18
, 5.4
22
Dic
arb
oxyl
ic a
cid
s*ox
alic
1.23
, 4.1
92
Succ
inic
4.19
, 5.4
82
Mal
onic
2.83
, 5.6
92
O-O
’ -D
imet
hyl-
3.77
, 5.9
42
Met
hyl-
3.05
, 5.7
62
(hig
h m
eltin
g)E
thyl
-2.
99, 5
.83
2 O
-O’ -
Dim
ethy
l-3.
94, 6
.20
2n-
prop
yl3.
00, 5
.84
2 (l
ow m
eltin
g)i-
prop
yl-
2.94
, 5.8
82
O,O
’ -D
ieth
yl-
3.63
, 6.4
62
Dim
ethy
l-3.
17, 6
.06
2 (
high
mel
ting)
Met
hyle
thyl
-2.
86, 6
.41
2 O
,O’ -
Die
thyl
-3.
51, 6
.60
2D
ieth
yl-
2.21
, 7.2
92
(low
mel
ting)
Eth
yl-n
-pro
pyl-
2.15
, 7.4
32
Tet
ram
ethy
l-3.
50, 7
.28
2D
i-n-
pro
pyl
-2.
07, 7
.51
2G
luta
ric
4.34
, 5.4
22
Ad
ipic
4.42
, 5.4
12
B-M
ethy
l4.
25, 6
.22
2Pi
mel
ic4.
48, 5
.42
2B
-Eth
yl4.
29, 6
.33
2Su
beri
c4.
52, 5
.40
2B
-n-P
rop
yl4.
31, 6
.39
2A
zela
ic4.
55, 5
.41
2B
,B-D
imet
hyl-
3.70
, 6.2
92
DL
-1:2
-Dic
hlor
osu
ccin
ic1.
68, 3
.18
20B
,B-M
ethy
leth
yl-
3.62
, 6.7
02
mes
o-1:
2-D
ichl
oros
ucc
inic
1.7
4, 3
.24
20B
,B-D
ieth
yl-
3.62
, 7.1
22
DL
-1:2
-Dib
rom
osu
ccin
ic1.
48, -
---
20B
,B-D
i-n-
pro
pyl
3.69
, 7.3
12
mes
o-1:
2-D
ibro
mos
ucc
inic
1.4
2, 2
.97
20D
-Tar
tari
c3.
03, 4
.45
20D
L-1
:2-D
imet
hyls
ucci
nic
3.93
, 6.0
020
DL
-Tar
tari
c3.
03, -
---
20m
eso-
1:2-
Dim
ethy
lsu
ccin
ic 3
.77,
5.3
620
mes
o-T
arta
ric
3.29
, 4.9
220
*All
are
ther
mod
ynam
ic v
alue
s
Ali
ph
atic
HO
-6.
332
Bic
yclo
[2.2
.2]o
ctan
e-1-
carb
oxyl
ic a
cid
s, 4
-su
bst
itu
ted
Br-
6.08
2
Lys
ergi
c ac
id, e
tc.
H-
6.75
2er
gom
etri
ne6.
8, --
2C
2H5O
2C-
6.31
2D
ihyd
roer
gom
etri
ne7.
4, --
2β-
dih
ydro
lyse
rgol
8.2,
--2
NC
-5.
902
Lyse
rgic
aci
d7.
8, 3
.32
C6H
5O-
3.53
*3.
95*
4.52
*α
-dih
ydro
lyse
rgic
8.3,
3.6
2C
H3-
3.91
*4.
24*
4.34
*er
gom
etri
nine
7.3,
--2
(CH
3)2C
H-
4.35
*α
-dih
ydro
lyse
rgol
8.3,
--2
(CH
3)3N
+ -1.
373.
453.
436-
met
hyle
rgol
ine
8.85
, --
2N
C-
3.60
*3.
55*
isol
yser
gic
acid
8.4,
3.4
2H
O2C
*2.
95*
3.54
3.51
γ-d
ihyd
roly
serg
ic8.
6, 3
.62
F 3C
-3.
79H
O-
2.98
*4.
08*
4.58
*I-
2.85
*3.
86*
Hyd
roxy
cycl
ohex
anec
arb
oxyl
ic a
cid
sC
l-2.
94*
3.83
*3.
99*
Cyc
lohe
xane
carb
oxyl
ic 4
.90
2(C
H3)
3Si-
4.24
*4.
27*
cis-
1,2
4.80
2C
2H5O
-4.
21*
4.17
*4.
45*
cis-
1,3
4.60
2i-
C3H
7O-
4.24
*4.
15*
4.68
*ci
s-1,
44.
842
n-C
5H11
O-
4.55
*tr
ans-
1,2
4.68
2C
6H5-
3.46
*tr
ans-
1,3
4.82
2C
H3C
H2-
3.77
4.35
*tr
ans-
1,4
4.68
2(C
H3)
3C-
3.46
4.28
4.40
*– H
O3P
-3.
784.
033.
95A
rom
atic
benz
ene-
CO
3H4.
20*
2– O
3S-
4.15
4.11
Ant
hrac
ene-
1-C
OO
H3.
692
H2N
-4.
984.
794.
92A
nthr
acen
e-9-
CO
OH
3.65
2(C
H3)
2N-
8.42
5.10
5.03
naph
thal
ene-
2-C
OO
H4.
172
– HO
3As-
4.22
Nap
htha
lene
-1-C
OO
H3.
692
– O2C
-5.
41**
4.60
4.82
CH
3NH
-5.
35.
105.
04S
ub
stit
ute
d b
enzo
ic a
cid
s (r
ef. 2
)C
OO
H*t
herm
odyn
amic
for
com
plex
che
lati
ng a
gent
s, s
ee a
lso
ref.
84.
see
also
pag
e 9a
for
mor
e ca
rbox
ylic
aci
ds.
Ben
zoic
aci
do
mp
Ort
ho-
sub
stit
ute
d b
enzo
ic a
cid
sH
-4.
20*
4.21
*B
enzo
ic a
cid
pK
Ref
.O
2N-
2.17
*3.
45*
3.44
2-C
H3-
3.91
**2
CH
3CO
-2-
t-C
4H9-
3.46
2C
H3S
O2-
3.64
*3.
52*
2,6-
(CH
3)2-
3.21
2C
H3S
-2,
3,4,
6-(C
H3)
4-4.
002
HS-
2,3,
5,6-
(CH
3)4-
3.52
2B
r-2.
85*
3.81
*4.
00*
2-C
2H5-
3.77
2F-
3.27
*3.
87*
4.14
*C
H3O
-4.
09*
4.09
*4.
47*
2-C
6H5-
3.46
**2
n-C
3H7O
-4.
24*
4.20
*4.
46*
2,4,
6-(C
H3)
3-3.
432
n-C
4H9O
-4.
25*
4.53
*2,
3,4,
5-(C
H3)
4-4.
222
Ben
zen
e P
olyc
arb
oxyl
ic a
cid
sR
ef. 2
Aci
dP
osit
ion
of
carb
oxyl
pK
Ip
KII
pK
III
pK
IVp
KV
pK
VI
Ben
zoic
14.
17*
Phth
alic
1,2
2.98
*5.
28*
Isop
htha
lic1,
33.
46*
4.46
*T
erep
htha
lic1,
43.
51*
4.82
*H
emim
ellit
ic1,
2,3
2.80
*4.
20*
5.87
*Tr
imel
litic
1,2,
42.
52*
3.84
*5.
20*
8T
rim
esic
1,3,
53.
12*
3.89
*4.
70*
Mel
loph
anic
1,2,
3,4
2.06
*3.
25*
4.73
*6.
21*
Preh
niti
c1,
2,3,
52.
38*
3.51
*4.
44*
5.81
*Py
rom
ellit
ic1,
2,4,
51.
92*
2.87
*4.
49*
5.63
*B
enze
nepe
ntac
arbo
xylic
1,2,
3,4,
51.
80*
2.73
*3.
97*
5.25
*6.
46*
Mel
litic
1.2,
3,4,
5,6
1.40
*2.
19*
3.31
*4.
78*
5.89
*6.
96*
*ion
ic s
tren
gth
0.03
2-M
etho
xyet
hylim
inod
iace
tic
2.2,
8.9
6**
ther
mod
ynam
ic2-
Met
hylt
hioe
thyl
imin
odia
ceti
c2.
1, 8
.91
oxal
ic a
cid*
1.25
, 4.1
4N
-n-p
ropy
lam
inoa
ceti
c2.
25, 1
0.03
Car
box
ylic
Aci
ds
Ref
. 77
N-2
-sul
foet
hylim
inod
iace
tic
1.
92, 2
.28,
8.1
6A
min
omal
onic
aci
d*
3.32
, 9.8
3α
-Bro
mob
utyr
ic a
cid
2.97
N-B
utyl
amin
oace
tic a
cid
2.29
, 10.
07N
-(ca
rbam
oylm
ethy
l)-i
min
o-d
iace
tic
acid
2.30
, 6.6
02-
carb
oxye
thyl
imin
odia
ceti
c ac
id2.
06, 3
.69,
9.6
6C
yano
met
hylim
inod
iace
tic
3.06
, 4.3
4β-
carb
oxym
ethy
lam
inop
ropi
onic
3.61
, 9.4
6α
,β-d
iam
inop
ropi
onic
aci
d1.
23, 6
.69
α,α
-dia
min
obut
yric
1.85
, 8.2
4, 1
0.44
Die
thyl
amin
oace
tic
2.04
, 10.
47D
i-(c
arbo
xym
ethy
l)-a
min
omet
hyl
phos
phon
icac
id2.
00, 2
.25,
5.5
7, 1
0.76
Dim
ethy
lam
inoa
ceti
c2.
08, 9
.80
N-e
thyl
amin
oace
tic
2.30
, 10.
10α
,β-d
imer
capt
osuc
cini
c2.
40, 3
.46,
9.4
4, 1
1.82
Glu
coni
c*3.
86β-
hyd
roxy
buty
ric
4.39
Ethy
lene
diam
ine-
N,N
-dia
cetic
5.58
, 11.
05α
-hyd
roxy
buty
ric
3.65
β-hy
dro
xypr
opio
nic
3.73
N-2
-hyd
roxy
ethy
limin
odia
ceti
c2.
2, 8
.73
Imin
odia
ceti
c*2.
98, 9
.89
3-hy
dro
xypr
opyl
imin
odia
ceti
c2.
06, 9
.24
β-io
dop
ropi
onic
*4.
04Im
inod
ipro
pion
ic4.
11, 9
.61
N-i
sopr
opyl
amin
oace
tic
2.36
, 10.
06Is
obut
yric
*4.
86α
-mer
capt
obut
yric
3.53
Man
delic
aci
d3.
41N
-met
hyla
min
oace
tic
2.24
, 10.
012-
Mer
capt
oeth
ylim
inod
iace
tic
Nitr
ilotr
iace
tic3.
03, 3
.07,
10.
-2.1
4, 8
.17,
10.
792-
Phos
phon
oeth
ylim
inod
iace
tic
Met
hylim
inod
iace
tic2.
81, 1
0.18
1.95
, 2.4
5, 6
.54,
10.
46
*The
rmod
ynam
ic
PH
EN
OL
S
Com
pou
nd
pK
Ref
.C
omp
oun
dp
KR
ef.
Chr
omot
ropi
c ac
id5.
36, 1
5.6
6R
esor
cino
l--
, 9.1
5 (3
0o)
50o-
Met
hoxy
phen
ol--
, 9.9
350
p-M
etho
xyph
enol
--, 1
0.16
50o-
Hyd
roxy
benz
-3-
Hyd
roxy
anth
ran-
ald
ehyd
e7.
9550
ilic
acid
10.0
9, 5
.20
512-
Am
ino-
4,5
dim
ethy
l-2-
Am
inop
heno
lph
enol
hyd
roch
lori
de10
.45.
2851
hydr
ochl
orid
e9.
99, 4
.86
514,
5-d
ihyd
roxy
benz
ene-
1,3
dis
ulp
honi
c ac
id7.
6612
.6e
Koj
ic a
cid
9.40
77
Ph
enol
om
pP
hen
olo
mp
H-
9.95
*9.
94*
O2N
-7.
23*
8.35
*7.
14*
(CH
3)3N
+-
7.42
88
OC
H-
6.79
8.00
7.66
CH
3SO
2-9.
337.
83N
C-
8.61
**7.
95C
H3C
O-
9.19
8.05
CH
3O2C
-8.
47*
C2H
5O2C
-8.
50*
n-C
4H9O
2C-
8.47
*C
3H5C
H2O
2C-
8.41
*I-
9.17
*B
r-8.
42*
9.11
*9.
34*
Cl-
8.48
*9.
02*
9.38
*F-
8.81
*9.
28*
9.95
*C
H3S
-9.
539.
53H
O-
9.48
9.44
9.96
HO
CH
2-9.
92*
9.83
*9.
82*
CH
3-10
.28*
10.0
8 10
.19*
C2H
5-10
.29.
910
.0C
H3O
-9.
939.
6510
.20
H2N
-9.
719.
8710
.30
- O2C
-9.
94*
9.39
*- O
3S-
9.29
9.03
--O
3P-
10.2
9.9
--O
3As
8.37
C6H
5-9.
939.
599.
51N
O-
6.35
**2-
Chl
oro-
4-N
itro
-5.
4279
2-N
itro
-4-C
hlor
o-6.
4679
* T
herm
odyn
amic
**R
efer
ence
52
AL
CO
HO
LS
an
d o
ther
OX
YG
EN
AC
IDS
Alc
ohol
s
Co
mp
ou
nd
pK
Ref
.C
om
po
un
dp
KR
ef.
Cho
line
13.9
6C
3F7•
CH
(C2F
5)•O
H10
.48
65C
hlor
al h
ydra
te9.
66, 1
1.0
61(C
3F7)
2CH
•OH
10.5
265
Tri
flu
oroe
than
ol12
.562
Car
boni
um io
nsC
F 3C
H2O
H11
.4, 1
2.43
63C
F 3C
H(O
H)C
H3
11.8
63T
rip
hen
ylm
eth
anol
s in
H
2SO
4 H
C1O
4 H
NO
3re
fC
F 3C
H2(
CH
3)3O
H12
.43
104,
4,4-
Tri
met
hoxy
.82.
.8
2
.80
66C
3F7C
H2O
H11
.4**
634,
4’-D
imet
hoxy
-1.2
4-1
.14
-1.1
166
(C3F
7)2C
HO
H10
.6**
634-
Met
hoxy
-3.4
0-3
.59
-3.4
166
HC
CC
H2O
H13
.55
644-
Met
hyl
-5.4
1-5
.67
66C
(CH
2OH
)) 414
.164
4 -T
ride
uter
iom
ethy
l- 5
.43
5.6
766
HO
CH
2CH
OH
CH
2OH
4.4
643,
3’,3
”-T
rim
ethy
l- 6
.35
-5.9
566
HO
CH
2CH
2OH
14.7
764
Un
sub
stit
ute
d t
rip
hen
yl-
CH
3CC
H2O
H14
.82
64m
etha
nol-
6.6
3-6
.89
6.60
66C
H3O
H15
.54
644,
4;,4
;-T
rich
loro
- 7
.74-
8.01
66C
H2=
CH
CH
2OH
15.5
264
4 -N
itro
-9.
15-
9.76
66H
2O15
.74
64C
Cl 3
CH
2OH
11.
8***
CH
3CH
2OH
1664
CF 3
CH
2OH
11.
3***
Su
bst
itu
ent
effe
cts
for
ion
izat
ion
of
RC
H2O
HR C
Cl- 3
12.2
4,11
.80
64,6
5C
F3-
12.3
764
CH
F 2C
H2-
12.7
464
Hyd
roxa
mic
aci
ds
CH
Cl 2
-12
.89
64Fu
ro-
8.45
72C
HE
C-
13.5
564
Gly
cine
7.40
72 H
2Cl-
14.3
164
Hip
puro
-8.
8072
CH
3CC
H2-
14.8
64is
oNic
otin
7.85
72H
OC
H2
15.1
64p-
Met
hylb
enz-
8.90
72H
-15
.564
Nic
otin
-8.
3072
CH
2=C
H-
15.5
64N
icot
in-m
ethi
odid
e6.
4672
CH
3-(e
xtra
p)(1
5.9)
64m
-Nit
robe
nz-
8.07
72C
F 3C
(CH
3)2O
H11
.664
Pico
lin8.
5072
HO
CH
2CF 2
CH
2OH
1164
Pyri
mid
ine-
2-ca
rbox
-7.
8872
Prim
ary
alco
hols
=R•C
H2•
OH
and
Sali
cyl-
7.43
72Se
cond
ary
alco
hols
in 5
0% a
lcoh
olT
ropo
-9.
0972
C2F
511
.35
65C
4F9
11.3
565
C5F
1111
.37
65C
7F15
11.3
565
Oth
er o
xyge
n a
cid
sC
HF 2
12.0
065
Trim
ethy
lam
ine-
n-ox
ide
4.6
18C
F 2C
l11
.63
65D
imet
hylg
lyox
ime
12.8
477
CH
F 2C
F 211
.34
65(5
0% d
ioxa
ne)
CH
F 2 •
(CF 2
) 211
.35
65O
-met
hyl e
ther
12.9
277
CF3
• C
H2
12.7
65T
ropo
lone
12a
77C
F 3 •
(CH
2)2
12.9
65α
-Bro
mot
ropo
lone
6.95
a77
CF 3
• C
HM
e •
OH
11.2
865
Ace
tald
hyd
rate
13.4
891
C3F
7 •
CH
Me
• O
H11
.38
65Fo
rmal
d hy
drat
e13
.29
91C
3F7C
HEt
• O
H11
.37
65C
3F7C
HPr
• O
H11
.37
65C
3F7
• C
H(C
F 3) •
OH
10.4
665
a 50%
dio
xane
***5
0 aq
uae
ous
etha
nol
OT
HE
R O
XY
GE
N A
CID
SH
ydro
xam
ic a
cid
sA
ceto
-9.
4068
Com
poun
dp
KR
ef.
n-B
utyr
o-9.
4868
Pyr
idin
e ox
ides
n-B
utyr
o-9.
0068
4-A
min
opyr
idin
e 1-
oxid
e3.
6967
p-M
etho
xybe
nzo-
9.19
684-
Dim
ethy
lam
inop
yrid
ine
1-ox
ide 3.88
67N
-Hyd
roxy
phth
alim
ide
7.00
, 6.1
071
, 72
Salic
ylo
7.32
684-
Dim
ethy
lam
inop
yrid
ine
1-ox
ide 3.88
67B
enzo
-8.
8868
p-C
hlor
oben
zo-
9.59
684-
Dim
ethy
lam
ino-
1-m
etho
xypy
rid
iniu
mpe
rchl
orat
e>
1167
α-N
apht
ho-
~7.
768
Prop
iono
-9.
4668
2-M
ethy
lam
inop
yrid
ine
1-ox
ide
2.61
672-
Am
ino-
1-m
etho
xypy
rid
iniu
m p
erch
lora
te12
.467
Oxi
mes
4-H
ydro
xypy
rid
ine
1-ox
ide
2.45
67B
enzo
phe
none
oxi
me
11.3
184-
Met
hoxy
pyri
din
e 1-
oxid
e2.
0567
Die
thyl
ket
oxim
e12
.618
1-M
etho
xypy
rid
i-4-
one
2.57
67Is
onit
roso
acet
ylac
eton
e (I
NA
A) 7
.476
2-H
ydro
xypy
rid
ine
1-ox
ide
-0.8
675-
Met
hyl-
1,2,
3-cy
cloh
exan
etri
one-
1,3-
dio
xim
e8.
376
2-E
thox
ypyr
idin
e 1-
oxid
e1.
1867
1-M
etho
xypy
rid
-2-o
ne-1
.3A
ceto
phe
none
oxi
me
11.4
818
4-M
ethy
lam
inop
yrid
ine
1-ox
ide
3.85
67A
ceto
xim
e11
.42
184-
Am
ino-
1-m
etho
xypy
rid
iniu
m p
erch
lora
te>
1167
Ison
itro
soac
eton
e (I
NA
) 8.3
76Sa
licyc
lald
oxim
e (S
A)
9.2
762-
Am
inop
yrid
ine
1-ox
ide
2.67
671,
2,3-
Cyc
lohe
xane
trio
netr
ioxi
me
8.0
762-
Dim
ethy
lam
inop
yrid
ine
1-ox
ide 2.27
675-
Met
hyl-
1,2,
3-cy
cloh
exan
e-tr
ione
trio
xim
e8.
076
2-M
ethy
lam
ino-
1-m
etho
xypy
rid
iniu
mto
luen
e-p-
sulp
hona
te>
1167
4-B
enzy
loxy
pyri
din
e 1-
oxid
e1.
9967
Oxy
gen
aci
ds
1-B
enzy
loxy
pyri
d-4
-one
2.58
67su
lfin
ic a
cid
s2-
Met
hoxy
pyri
din
e 1-
oxid
e1.
2367
p-T
olue
ne-
1.99
731-
Ben
zylo
xypy
rid
-2-o
ne-1
.767
p-C
hlor
oben
zene
-73
p-N
itro
benz
ene-
73P
yrid
ine
1-ox
ides
p-B
rom
oben
zene
-1.
8973
Rp
KR
ef.
m-N
itro
benz
ene-
1.88
734-
CH
31.
2947
Ben
zene
-1.
84, 2
.16
733-
CH
31.
0847
Per
oxya
cid
s3,
4-(C
H) 4
1.01
47Pe
roxy
mon
osul
furi
c9.
469
3-C
OO
C4H
90.
0347
Ace
tic8.
270
4-N
O2
-1.7
47n-
But
yric
8.2
703-
NH
21.
4747
Form
ic7.
170
H0.
7947
Prop
ioni
c8.
170
3-C
OO
H0.
0947
pero
xyd
ipho
spho
ric
5.18
, 7.8
854-
CO
OH
-0.4
847
per
oxym
onop
hosp
hori
c 4.
8590
Per
oxid
es R
OO
H (R
ef. 7
0)H
CH
3C
2H5
iso-
C3H
7te
rt-C
4H9
iso-
C4H
911
.611
.511
.812
.112
.812
.8
Oxi
mes
ref.
93Py
rid
ine-
2-al
dox
ime
hept
iod
ide
8.00
benz
oqu
inol
ine
mon
-6.
25Py
rid
ine-
4-al
dox
ime
met
hiod
ide
8.50
3-py
rid
ine-
1,2-
etha
ned
ione
-2-o
xim
em
ethi
odid
e7.
20Py
rid
ine-
4-al
dox
ime
pent
iod
ide
8.50
4-Py
rid
ine-
1,2-
etha
ned
ione
-2-o
xim
em
ethi
odid
e7.
1O
-Met
hylt
yros
ine
ethy
l est
er 7
.31
22oc
topi
ne 1
3, 1
.36
8.77
6Py
rid
ine-
2-al
dox
ime
met
hiod
ide
8.0
Phen
ylgl
yoxa
ld-
8.3
2.40
Pyri
dine
-4-a
ldox
ime
dod
ecio
did
e8.
5Ph
enyl
alan
ine
1.83
9.13
6Py
rid
ine-
3-al
koxi
me
met
hiod
ide
9.2
2-Py
rrol
idoo
ne-5
-car
boxy
lic a
cid
(glu
cam
icac
id)
3.32
Hyd
roxa
mic
aci
ds
ref.
93Se
rine
2.21
9.15
6D
-Lys
ine-
7.93
Thr
eoni
ne2.
6310
.43
6N
-phe
nyln
icot
ino-
8.00
N-T
rim
ethy
l tyr
osin
e9.
7521
Chl
oroa
ceto
-8.
40T
yros
ine
10.
07, 2
.20
9.11
Form
o-8.
65U
roca
nic
acid
5.8
3.5
p-C
hlor
ophe
noxy
acet
o-8.
75V
alin
e2.
329.
626
p-H
ydro
xybe
nzo-
8.93
β-A
lani
ne3.
6010
.19
6p
-Met
hoxy
benz
o-9.
00γ-
Am
inob
utyr
ic a
cid
4.23
10.4
36
N-P
heny
lben
zo-
9.15
Arg
inin
e 12
.48
2.17
9.04
6o-
Am
inob
enzo
-9.
17A
spar
agin
e2.
028.
86
L-T
yros
ine
9.20
Aza
seri
ne8.
556
L-L
ysin
e7.
9C
anav
anin
e7.
40, 9
.25
11.5
0 (?
)6
p-N
itro
benz
o-8.
0C
reat
ine
2.67
11.0
26
p-A
min
oben
zo-
9.3
Cys
tein
e 10
.78
1.71
8.33
6L-
Lact
i-9.
33,
4-D
ihyd
roxy
phen
ylal
anin
ePr
opio
no-
9.4
9.88
, 2.3
68.
686
Phth
alo-
9.4
11.6
8In
dol
e-3-
acet
o-9.
5G
luta
min
e2.
179.
136
Cyc
lohe
xano
-9.
7H
ista
min
e 5.
09.
76
Hex
ano-
9.7
β-H
ydro
xygl
utam
ic2.
099.
206
acid
4.18
Am
ino
Aci
dsH
ydro
xypr
olin
e1.
929.
736
Com
poun
dp
KR
ef.
Leu
cine
2.36
9.60
6-C
OO
H-N
H3
Met
hion
ine
2.28
9.21
Ala
nine
2.35
9.69
61-
Met
hylh
istid
ine
6.48
, 1.6
98.
856
α-A
min
obut
yric
aci
d2.
559.
60N
orle
ucin
e2.
399.
766
α-A
min
oiso
buty
ric
2.36
10.2
16
Nor
valin
e2.
369.
766
Arg
inin
osuc
cini
c
>12
, 1.6
29.
586
Orn
ithi
ne1.
718.
696
2.70
, 4.2
610
.76
Asp
artic
aci
d2.
09, 3
.86
9.82
6Pr
olin
e1.
9910
.60
6C
anal
ine
10.3
, 9.2
011
.6 (?
)6
Sarc
osin
e2.
2310
.01
6C
reat
inin
e4.
849.
26
Tau
rine
1.5
8.74
6C
ysti
ne1.
657.
856
Thio
lhis
tidin
e <1
.5, 1
1.4
2.26
9.85
61.
848.
476
Diid
otyr
osin
e6.
48, 2
.12
7.82
6T
rypt
opha
n2.
389.
396
Glu
tam
ic a
cid
2.19
, 4.2
59.
676
Tyr
osin
e et
hyl e
ster
7.3
39.
8022
Gly
cine
2.34
9.6
6P
epti
des
His
tidin
e6.
0, 1
.82
9.17
6A
nser
ine
7.0
2.65
9.5
6C
arno
sine
6.8
3--
9.51
6H
ydro
xyls
ine
2.13
8.62
6C
ysti
nyld
igly
cine
3.12
6.36
69.
673.
126.
95Is
oleu
cine
2.36
9.68
6G
lycy
lgly
cine
3.06
8.1
3L
ysin
e2.
188.
956
Gly
-gly
-gly
3.26
7.91
2310
.53
Gly
cylp
rolin
e2.
848.
556
O-M
ethy
l tyr
osin
e9.
2721
Asp
arty
l his
ti-2.
457.
98
din
e6.
823.
02G
ly-g
ly-g
ly-g
ly3.
057.
7523
Dig
lycy
lcys
tine
2.71
7.94
6Ly
syl-
lysi
ne (L
,L)
3.01
7.53
6G
luta
thio
ne 9
.12
2.12
8.66
610
.05
11.0
13.
53
Com
poun
d-C
OO
H-N
H2
-NH
2-N
H2
-NH
2R
ef.
Gly
•Ala
(L) o
r (D
)3.
178.
2327
Ala
•Gly
(L) o
r (D
)3.
168.
2427
Gly
•Ala
•Ala
(LL)
3.38
8.10
27G
ly•A
la•A
la (L
D)
3.30
8.17
27A
la•A
la•O
H (D
D)
3.30
8.14
27A
la•A
la•O
H (L
D)
3.12
8.30
27H
•Ala
•Ala
•Ala
•OH
(3L)
3.39
8.03
27H
•Ala
•Ala
•Ala
•OH
(LLD
)3.
378.
0527
H•A
la-A
la-A
la•O
H (L
DL)
3.31
8.13
27H
•Ala
-Ala
-Ala
•OH
(DLL
)3.
378.
0627
H-A
la-A
la-A
la•O
H (3
D)
3.39
8.06
27H
•Ala
-Ala
-Ala
-Ala
•OH
(4L)
3.42
7.94
27H
•Ala
-Ala
-Ala
-Ala
•OH
(LLD
L)3.
247.
9327
H•A
la-A
la-A
la-A
la•O
H (L
DLL
)3.
227.
9927
H•A
la-A
la-A
la-A
la•O
H (D
LLL)
3.42
7.99
27H
•Lys
-Ala
•OH
(LL)
3.22
7.62
10.7
027
H•L
ys-A
la•O
H (L
D)
3.00
7.74
10.6
327
H•A
la-L
ys-A
la•O
H (3
L)3.
157.
6510
.30
27H
•Ala
-Lys
-Ala
•OH
(LD
L)3.
337.
9710
.36
27H
•Ala
-Lys
-Ala
•OH
(LLD
)3.
297.
8410
.49
27H
•Ala
-Lys
-Ala
-Ala
•OH
(4L)
3.58
8.01
10.5
827
H•A
la-L
ys-A
la•O
H (L
DLL
)3.
328.
0110
.37
27H
•Ala
-Lys
-Ala
-Ala
-Ala
•OH
(5L)
3.53
7.75
10.3
527
H•A
la-L
ys-A
la-A
la-A
la•O
H (L
DLL
L)3.
307.
8510
.29
27H
•Lys
-Lys
•OH
(LL
)3.
017.
5310
.05
11.0
127
H•L
ys-L
ys•O
H (L
D)
2.85
7.53
9.92
10.9
827
H•L
ys-L
ys•O
H (3
L)3.
087.
349.
8010
.54
11.3
227
H•L
ys-L
ys-L
ys•O
H (L
DL)
2.91
7.29
9.79
10.5
411
.42
27H
•Lys
-Lys
-Lys
•OH
(LD
D)
2.94
7.14
9.60
10.3
811
.09
27C
ompo
und
pK
ref.
Glu
tath
ione
3.59
, 8.7
5, 9
.65
77G
lycy
lser
ine
8.23
77G
lycy
lleuc
ine
8.13
77Le
ucyl
glyc
ine
7.96
77G
lycy
lisol
euci
ne7.
9677
Leuc
ylgl
ycyl
glyc
ine
7.66
77G
lycy
lphe
nyla
lani
ne8.
2877
Gly
cylt
yros
ine
8.22
77Be
nzyl
glut
amic
aci
d3.
49, 4
.99
77G
lycy
ltry
ptop
hane
8.04
77G
luta
thio
ne, o
xidi
zed
3.15
, 4.0
3, 8
.57,
9.5
477
Ala
nyla
lani
ne (L
L)3.
308.
1492
Ala
nyla
lani
ne (L
D)
3.12
8.30
92Ly
syla
lani
ne (L
L)3.
227.
6210
.70
92Ly
syla
lani
ne (L
D)
3.00
7.74
10.6
392
Leu
cylt
yros
ine
(LL
)3.
467.
8410
.09
92L
eucy
ltyr
osin
e (D
L)
3.12
8.38
10.3
592
Lysy
llysi
ne (L
D)
2.85
7.53
9.92
92N
ITR
OG
EN
CO
MP
OU
ND
SA
lip
hat
ic A
min
es
p
Kre
f.A
mm
onia
9.21
1n-
Prop
yl-
10.5
31
Prim
ary
Am
ines
Tri
met
hyls
ilym
ethy
l-10
.96
1β-
Ala
nine
est
er9.
131
CH
3ON
H2
4.60
12A
llyla
min
e-9.
692
Ally
l-9.
491
Ben
zyl
9.34
1γ-
Am
ino-
n-bu
tyri
c ac
id e
ster
9.7
11
n-B
utyl
-10
.59
1se
c-B
utyl
-10
.56
1t-
But
yl-
10.5
51
Cyc
lohe
xyl-
10.6
41
Cyc
lohe
xylm
ethy
l-10
.49
1β-
dif
luor
oeth
yl-
7.52
1E
than
ol-
9.50
1E
thyl
10.6
31
Eth
ylen
edi-
9.98
, 7.5
21,
77
Gly
cine
est
er7.
751
Hyd
razi
ne8.
101
Hyd
roxy
l-5.
971
Isop
ropy
l-10
.63
1M
etho
xy-
4.60
1M
ethy
l-10
.62
1ne
o-Pe
ntyl
-10
.21
1Ph
enyl
amyl
-10
.49
2δ-
Phen
ylbu
tyl
10.4
02
β-Ph
enyl
ethy
l-9.
831
γ-Ph
enyl
prop
yl-
10.2
01
Tri
ethy
lene
di-
8.8*
?
XX
NH
3+X
CH
2NH
3+X
(CH
2)2N
H3+
X(C
H2)
3NH
3+X
(CH
2)4N
H3+
X(C
H2)
5NH
3+re
f.
H-
9.25
*10
.64*
10.6
7*10
.58*
10.6
1*10
.63*
2H
F 2C
-7.
52R
O2C
-7.
759.
139.
7110
.15*
10.3
72
HO
-5.
96*
9.50
*C
6H5-
4.58
*9.
37*
9.83
*10
.20*
10.3
9*10
.49*
2H
2N-
8.12
*9.
98*
10.6
5*10
.84*
11.0
5*2
H2C
=C
H-
9.69
CH
3-10
.64*
10.6
7*10
.58*
10.6
1*10
.63*
10.6
4*2
X-H
-NH
3+-C
O2–
-SO
3–-P
O3–
2X
-NH
3+9.
25*
-.88
110
.25
X(C
H2)
2NH
3+10
.64
9.77
5.75
10.8
X(C
H2)
2NH
3+10
.67
10.1
99.
2010
.8X
(CH
2)4N
H3+
10.6
19.
3110
.77
10.6
510
.9X
(CH
2)5N
H3+
10.6
39.
7410
.75
10.9
511
.0X
(CH
2)8N
H3+
10.6
510
.10
X(C
H2)
10N
H3+
10.6
411
.35
11.2
5X
(CH
2)3N
H3+
10.5
88.
5910
.43
10.0
5
Sec
ond
ary
amin
esD
i-n-
buty
l-11
.25
1D
imet
hyl-
10.6
41
Diis
obut
yl-
10.5
01
Di-
n-pr
opyl
-11
.00
1α
-Eth
ylpy
rrol
ine
7.43
2D
iisop
ropy
l-11
.05
1α
-Ben
zylp
yrro
line-
7.08
2t-
But
ylcy
cloh
exyl
-11
.23
12-
Met
hylp
iper
idin
e10
.99
2α
-Cyc
lohe
xylp
yrro
line
7.95
2α
-Cyc
lohe
xylp
yrro
lidin
e10
.80
2α
-(p-
Tol
yl)p
yrro
line
7.59
2α
-(p-
Tol
yl)p
yrro
lidin
e10
.01
2α
-Eth
ylpy
rrol
idin
e10
.43
2N
,O-d
imet
hylh
ydro
xyla
min
e 4.
7512
α-B
enzy
lpyr
rolid
ine
10.3
62
Ace
tani
lide
+0.
614
N-m
ethy
lhyd
roxy
lam
ine
5.96
12*t
herm
odyn
amic
val
ueD
ieth
yl-
10.9
81
Ali
ph
atic
Am
ines
Met
hyl-β-
die
thyl
amin
o-et
hyl-
sulf
ide
1,2-
Imin
oeth
ane
7.98
71,
2-D
imet
hyl-Δ2
-pyr
rolin
e11
.94
2ci
s-2,
3-Im
inob
utan
e8.
727
1-m
ethy
l-2-
n-bu
tyl-Δ2
-pyr
rolin
e 11
.90
1,2-
Imin
o-2-
met
hylp
rop
ane
8.61
71-
Eth
yl-2
-met
hyl-Δ2
-pyr
rolin
e11
.92
21,
2-Im
inob
utan
e8.
297
1-n-
But
yl-2
-met
hyl-Δ2
-pyr
rolin
e 11
.90
2tr
ans-
2,3-
Imin
obu
tane
8.69
71,
2-D
imet
hyl-Δ2
-tet
rahy
dro
pyri
din
e11
.57
2S
econ
dar
y A
min
esN
-Eth
yl d
eriv
ativ
e of
: 1,
2-Im
ino-
etha
ne7.
937
Ally
lmet
hyl-
10.1
11
Ben
zyle
thyl
-9.
681
Tra
ns-2
,3-I
min
obut
ane
9.47
7M
orph
olin
e8.
361
Tri
met
hylh
ydro
xyla
min
e3.
6512
N-B
enzo
ylpi
pera
zine
7.78
1D
imet
hyle
thyl
-9.
991
Di-
sec-
buty
l-11
.01
1T
riet
hyl-
10.6
51
N-M
ethy
lmet
hoxy
amin
e4.
751
Dim
ethy
l-n-
buty
l-10
.02
1Py
rolid
ine
11.2
71
Dim
ethy
l-is
opro
pyl-
10.3
01
1-T
osyl
pipe
razi
ne7.
39D
imet
hyl-
t-bu
tyl-
10.5
21
Ben
zylm
ethy
l-9.
581
Tri
-n-b
utyl
-10
.89
1Pi
peri
dine
11.2
21
Dia
llylm
ethy
l-8.
791
N-C
arbe
thox
ypip
eraz
in8.
281
1-n-
Prop
ylpi
peri
din
e10
.48
2D
ietr
imet
hyls
ilylm
ethy
l-11
.40
110
.110
.15
Dia
llyl-
9.29
19.
8--
5N
-Met
hylh
ydro
xyl-
5.96
11,
2-D
imet
hylp
yrro
lidin
e10
.26
2T
rim
ethy
lene
imin
e11
.29
11-
Met
hyl-
2-n-
buty
lpyr
rolid
in10
.24
2C
is-2
,6-d
imet
hyl-
pipe
rid
ine
10.9
23
1-E
thyl
-2-m
ethy
lpyr
rolid
ine
10.6
42
1-n-
But
yl-2
-met
hylp
yrro
lidin
e 10
.43
21-
Eth
yl-2
-met
hylp
yrro
lidin
e10
.70
21,
2-Im
inob
utan
e8.
187
Ter
tiar
y am
ines
cis-
2,3-
Imin
obut
ane
8.56
7T
rim
ethy
l-9.
761
N-d
imet
hylh
ydro
xyla
min
e5.
2012
Dim
ethy
ldie
thyl
-10
.29
1A
llyld
imet
hyl
8.78
1D
imet
hyl-
n-pr
opyl
-9.
991
1,2-
Dim
ethy
lpip
erid
ine
10.2
62
Dim
ethy
l-is
obut
yl-
9.91
11-
Eth
yl-2
-met
hyl-Δ2
-tet
rahy
dro
pyri
din
e11
.57
2D
imet
hyl-
sec-
buty
l-10
.40
1T
ri-n
-pro
pyl-
10.6
51
Tria
llyl-
8.31
1N
-Ally
lpip
erid
ine
9.69
21-
Die
thyl
amin
o-he
xane
-thi
ol-(
6)C
yan
oam
ines
2-A
min
o-2-
cyan
opro
pane
5.3
9N
-pip
erid
ine-
CH
2CN
4.55
8β-
Isop
ropy
lam
inop
ropi
onit
rile
8.0
9E
t 2N
CN
-2.0
8β-
Die
thyl
amin
opro
pion
itri
le7.
69
Et 2
N(C
H2)
2CN
7.65
8E
t 2N
CH
2CN
4.55
8E
t 2N
(CH
2)4C
N10
.08
8E
t 2N
(CH
2)3C
N9.
298
Et 2
NC
(CH
3)2C
N9.
138
Et 2
N(C
H2)
5CN
10.4
68
EtN
(CH
2CN
) 2-0
.68
HN
(CH
2CN
) 20.
28
EtN
(CH
2CH
2CN
) 24.
558
HN
(CH
2CH
2CN
) 25.
268
H2N
CH
2CN
5.34
8N
(CH
2CH
2CN
) 31.
18
N-A
mph
etam
ine-
(CH
2)2-
CN
7.23
8N
-pip
erid
ine-
C(C
H3)
2CN
9.22
8N
-Nor
cod
eine
-(C
H2)
2CN
5.68
8N
-Met
ham
phe
tam
ine-
(CH
2)2C
N 6
.95
8D
imet
hylc
yani
mid
e1.
29
Met
hyl c
yana
mid
e1.
29
Die
thyl
cyan
imid
e1.
29
Eth
yl c
yana
mid
e1.
29
Am
inoa
ceto
nitr
ile5.
39
Cya
nam
ide
1.1
9D
ieth
ylam
inoa
ceto
nitr
ile4.
59
Dim
ethy
lam
inoa
ceto
nitr
ile4.
29
β-A
min
opro
pion
itri
le7.
79
CF
3CH
2NH
CH
36.
0510
β-D
imet
hyla
min
opro
pion
itri
le7.
09
Ph
enyl
eth
ylam
ines
β,β"
-Dic
yano
die
thyl
amin
e5.
29
2-ph
enyl
ethy
lam
ine
9.78
11Fo
rco
mpl
ex c
hela
ting
age
nts
of a
lipha
tic
amin
es,
see
also
ref
. 77.
N-m
ethy
l-2-
(3,4
-dih
ydro
xyph
enyl
)-et
hyla
min
e8.
7811
N-m
ethy
l-2-
phen
yl10
.31
11Fl
uor
o-su
bst
itu
ted
am
ines
Epi
neph
rine
8.55
11C
F3C
H2N
H2
5.7
10A
rter
enol
8.55
11C
F3C
H2N
(CH
3)2
4.75
10
R2
R1
CH
CH
2NH
R4
R3
ref.
11
R1
R2
R3
R4
pK
HH
HH
9.78
HH
OH
H8.
90H
OH
OH
H8.
81O
HH
OH
H8.
67H
OH
HH
9.22
OH
OH
HH
8.93
OH
OH
OH
H8.
58H
HH
CH
310
.31
HH
OH
CH
39.
31H
OH
OH
CH
28.
62O
HH
OH
CH
38.
89H
OH
HC
H3
9.36
OH
OH
HC
H3
8.78
OH
OH
OH
CH
38.
55
Rin
g am
ines
and
imin
es (i
n 80
% m
ethy
l cel
loso
lve)
(ref
. 2)
Pen
tam
ethy
lene
9.99
Cyc
lotr
idec
yl9.
63H
exam
ethy
lene
10.0
0C
yclo
tetr
adec
yl9.
54H
epta
met
hyle
ne9.
77C
yclo
pent
adec
yl9.
54O
ctam
ethy
lene
9.39
Cyc
lohe
ptad
ecyl
9.57
Non
amet
hyle
ne9.
14C
yclo
octa
dec
yl9.
54D
ecam
ethy
lene
9.04
Und
ecam
ethy
lene
9.14
Am
ines
oth
erD
odec
amet
hyle
ne9.
31D
imeo
one
5.23
18T
rid
ecam
ethy
lene
9.35
Phth
alim
ide
8.30
18T
etra
dec
amet
hyle
ne9.
35N
itro
urea
4.57
18H
exad
ecam
ethy
lene
9.29
Nit
rour
etha
ne3.
2818
Hep
tad
ecam
ethy
lene
9.27
Dip
heny
lthi
ocar
bazo
ne4.
56
Cyc
lohe
xyl
9.82
β,β,β"
-Tri
amin
otri
ethy
lam
ine
Cyc
lohe
ptyl
9.99
8.42
, 9.4
4, 1
0.13
87C
yclo
octy
lC
yclo
nony
l9.
95A
nil
ines
Ref
. 2C
yclo
dec
yl9.
85M
onos
ub
stit
ute
dC
yclo
und
ecyl
9.71
Su
bst
itu
ent
om
pC
yclo
dod
ecyl
9.62
H-
4.62
*4.
64*
4.58
*
(CH
3)3N
+ -2.
262.
51p-
(CH
3)3C
-4.
65m
-Br-
3.08
CH
3O2C
-2.
163.
562.
30m
-Cl-
3.09
CH
3SO
2-2.
68*
1.48
p-F-
4.01
CH
3S-
4.05
4.40
p-(C
H3)
3Si-
3.99
Br-
2.60
*3.
51*
3.91
*p-
CH
3O-
5.14
, 5.1
6F-
2.96
*3.
38*
4.52
*C
H3O
-4.
49*
4.20
*5.
29*
C6H
5-3.
78*
4.18
4.27
*(C
H3)
3C-
3.78
– O3S
-3.
803.
32H
3N+
1.3
2.65
3.29
O2N
--0
.28*
2.45
*0.
98*,
1.1
1*H
O2C
-2.
043.
052.
32C
2H5O
2C-
2.10
2.38
F 3C
-3.
49*
2.57
*H
O-
4.72
4.17
5.50
Cl-
2.62
*3.
32*
3.81
*(C
H3)
3Si-
4.64
*4.
36*
C2H
5O-
4.47
*4.
17*
5.25
*C
H3-
4.38
*4.
67*
5.07
*– H
O3A
s3.
774.
054.
05H
2N-
4.47
4.88
6.08
*The
rmod
ynam
ic
Dim
eth
ylH
5.07
52m
-NO
22.
6352
m-C
N2.
9752
p-N
O2
0.61
52p-
CN
1.78
52p-
NO
4.54
52
Dim
eth
yl (i
n 50
% e
than
ol)
Su
bst
itu
ent X
C6H
4N(C
H3)
2re
f. 2
H-
4.21
, 4.0
9m
-CH
34.
66p-
C2H
5-4.
69o-
(CH
3)2C
H-
5.05
p-C
H3C
H2C
H2C
H2-
4.62
o-(C
H3)
3C-
4.26
p-I-
3.43
, 2.7
3p-
Br-
3.52
, 2.8
2p-
Cl-
3.33
m-(
CH
3)3S
i-4.
41o-
CH
3O-
5.49
o-C
H3
5.15
, 5.0
7p-
CH
34.
94p-
CH
3CH
2CH
2-4.
43p-
(CH
3)2C
H-
4.77
p-(C
H3)
2CH
CH
2-4.
19
Ort
ho-
sub
stit
ute
d a
nil
ines
(in
50%
eth
anol
)1-
NH
2-8-
NO
2-2.
79H
-4.
251-
NH
2-8-
SO3-
1.71
2-C
H3-
3.98
, 4.0
91-
NH
2-3-
SO3-
3.20
*2,
3-(C
H3)
2-4.
421-
NH
2-4-
SO3-
2.81
*2,
4-(C
H3)
2-4.
611-
NH
2-5-
SO3-
3.69
*2,
5-(C
H3)
2-4.
17, 4
.23
1-N
H2-
6-SO
3-3.
80*
2,6-
(CH
3)2-
3.42
, 3.4
91-
NH
2-7-
SO3-
3.66
3,5-
(CH
3)2-
4.48
1-N
H2-
8-SO
3-5.
03*
2-C
H3-
4.09
2-N
H2-
4.11
*2-
(CH
3)2C
H-
4.06
2-N
H2-
1-N
O2-
-1.0
2-(C
H3)
2C-
3.38
2-N
H2-
3-N
O2-
2.93
2,6-
(CH
3)2-
4-(C
H3)
3C-
3.88
2-N
H2-
4-N
O2-
2.63
2,4-
(CH
3)2-
6-(C
H3)
3-3.
432-
NH
2-5-
NO
2-3.
162-
CH
3-4,
6-(C
H3)
3C-
3.31
2-N
H2-
6-N
O2-
2.75
2,4,
6-[(
CH
3)3C
3]-
<2
2-N
H2-
7-N
O2-
3.13
2-N
H2-
8-N
O2-
2.86
Su
bst
itu
ted
Nap
hth
ylam
ines
2-N
H2-
1-SO
3-2.
351-
NH
2-3.
92*
2-N
H2-
3-SO
3---
1-N
H2-
2-N
O2-
-1.6
2-N
H2-
4-SO
3-3.
701-
NH
2-3-
NO
2-2.
222-
NH
2-5-
SO3-
3.96
*1-
NH
2-4-
NO
2-0.
542-
NH
2-6-
SO3-
3.74
*1-
NH
2-5-
NO
2-2.
802-
NH
2-7-
SO3-
3.95
*1-
NH
2-6-
NO
2-3.
152-
NH
2-8-
SO3-
3.89
*1-
NH
2-7-
NO
2-2.
83
N-s
ub
stit
ute
d a
nil
ines
*R
C6H
5NH
RC
6H5N
(CH
3)R
C6H
5NR
22-
CH
3C6H
4NH
R2-
CH
3C6H
4NR
2H
-4.
584.
854.
584.
394.
39C
H3-
4.85
5.06
5.06
4.59
5.86
C2H
5-5.
115.
986.
564.
927.
18n-
C3H
7-5.
02--
5.59
--n-
C4H
9-4.
95--
~5.
7--
i-C
4H9-
--5.
20--
--se
c-C
4H9-
--6.
04--
--t-
C6H
12-
6.30
----
--C
yclo
pent
yl-
5.30
6.71
--5.
07C
yclo
hexy
l-5.
606.
35--
5.34
t-C
4H9-
6.95
7.52
--6.
49*T
herm
odyn
amic
AM
INE
Sre
f. 77
Sec
ond
ary
amin
esN
-But
ylam
inoa
cetic
aci
d2.
29, 1
0.07
Prim
ary
amin
esN
,N'-D
ieth
ylet
hyle
ned
iam
ine
7.70
, 10.
462-
amin
oeth
ylsu
lpho
nic
acid
9.08
2,2'
-dih
ydro
xyd
ieth
ylam
ine
9.00
Am
inom
alon
ic a
cid
3.32
, 9.8
3N
,N'-d
i-n-
prop
ylet
hyle
ned
iam
ine
8.14
, 10.
97N
-n-b
utyl
ethy
lene
dia
min
e7.
53, 1
0.30
Eth
ylen
edia
min
e-N
,N'-d
iace
tic
acid
6.4
2, 9
.46
2,3-
dia
min
obu
tane
, mes
o6.
92, 9
.97
Imin
odip
ropi
onic
aci
d4.
11, 9
.61
2,3-
dia
min
obut
ane,
rac
emic
6.91
, 10.
00Pi
pera
zine
5.68
, 9.8
22,
2'-d
iam
inod
ieth
yl s
ulfi
de8.
84, 9
.64
β-ca
rbox
ymet
hyla
min
opro
pion
ic a
cid
1,3-
dia
min
o-2,
2-d
imet
hylp
ropa
ne 8
.18,
10.
223.
61, 9
.46
N,N
'-Di-
(2-a
min
oeth
yl)-
ethy
lene
dia
min
e3.
32, 6
.67,
9.2
0, 9
.92
N,N
'-Dim
ethy
leth
ylen
edia
min
e7.
40, 1
0.16
N-e
thyl
amin
oace
tic
acid
2.30
, 10.
101,
2-d
iam
ino-
2-m
ethy
lpro
pane
6.79
, 10.
00Im
inod
iace
tic a
cid
2.98
, 9.8
91,
3-D
iam
inop
ropa
n-2-
ol8.
23, 9
.68
N-i
sopr
opyl
amin
oace
tic
acid
2.36
, 10.
06N
,N'-D
igly
cyet
hyle
ned
iam
ine
7.63
, 8.3
5N
-n-p
ropy
lam
inoa
ceti
c ac
id2.
28, 1
0.03
Ethy
lene
diam
ine-
N,N
-dia
cetic
aci
d 5.
58, 1
1.05
Furf
uryl
amin
e8.
89T
erti
ary
amin
es2-
(2-h
ydro
xypr
opyl
amin
o)-e
thyl
amin
e6.
94,
9.86
4-(2
-am
inoe
thyl
)mor
phol
ine
4.84
, 9.4
5D
i-(2
-hyd
roxy
ethy
l)am
inoa
ceti
c ac
id8.
082-
(3-h
ydro
xyp
rop
ylam
ino)
ethy
lam
ine
Hex
amet
hyle
nete
tram
ine
5.13
6.78
, 9.7
6M
ethy
limin
odia
cetic
aci
d2.
81, 1
0.18
N-M
ethy
lam
inoa
ceti
c ac
id2.
24, 1
0.01
Die
thyl
amin
oace
tic a
cid
2.04
, 10.
47M
ethy
l-α
-am
ino-β-
mer
cap
top
roio
nate
6.56
,8.
99D
imet
hyla
min
oace
tic a
cid
2.08
, 9.8
0N
-2-h
ydro
xyet
hylim
inod
iace
tic
acid
2.2
, 8.7
3N
-n-p
ropy
leth
ylen
edia
min
e7.
54, 1
0.34
Tri
ethy
lene
dia
min
e4.
18, 8
.19
1,2,
3-tr
iam
inop
ropa
ne3.
72, 7
.95,
9.5
9T
ris-
(hyd
roxy
met
hyl)
-am
inom
etha
ne8.
10R
ef. 1
2-am
ino-
2'-h
ydro
xyd
ieth
yl s
ulfi
de
9.04
Dia
llylm
ethy
l8.
79N
-(ca
rbam
oylm
ethy
l)-i
min
odia
ceti
c ac
id2.
30, 6
.60
Ben
zyld
imet
hyl
8.93
N-A
llylp
iper
idin
e9.
682,
2'-d
iam
inod
ieth
ylam
ine
3.58
, 8.8
6, 9
.65
N-A
llylm
orph
olin
e7.
052,
3-d
iam
ino-
2,3-
dim
ethy
lbut
ane
6.56
, 10.
13Pr
opar
gyld
imet
hyl
7.05
3,3'
-dia
min
odi-
n-pr
opyl
amin
e8.
02,9
.70,
10.
7Pr
opar
gyle
thyl
dim
ethy
l8.
881,
2-D
i-(2
-am
inoe
thyl
thio
)eth
ane
8.43
, 9.3
2N
-Met
hylm
orph
olin
e7.
411,
2-d
iam
inop
ropa
ne7.
13, 1
0.00
N-M
ethy
lpyr
rolid
ine
10.4
6N
,N-d
ieth
ylet
hyle
ned
iam
ine
7.07
, 10.
02N
,N-D
imet
hylh
ydro
xyla
min
e5.
20N
,N-d
imet
hyle
thyl
ened
iam
ine
6.63
, 9.5
3A
llyld
imet
hyl
8.73
N-E
thyl
ethy
lene
dia
min
e7.
63, 1
0.56
Ben
zyld
ieth
yl9.
48N
-(2-
hyd
roxy
ethy
l)-e
thyl
ened
iam
ine
N-E
thyl
pipe
ridi
ne10
.40
6.83
, 9.8
2N
-Eth
ylm
orph
olin
e7.
70N
-iso
prop
ylet
hyle
ned
iam
ine
7.70
, 10.
62P
rop
argy
met
hyld
imet
hyl
8.33
2-M
etho
xyet
hyla
min
e9.
20N
-Met
hylp
iper
idin
e10
.08
Mer
capt
oeth
ylam
ine
8.27
, 10.
53N
-Met
hylt
rim
ethy
lene
imin
e10
.40
N-M
ethy
leth
ylen
edia
min
e7.
56, 1
0.40
Tri
etha
nola
min
e7.
772-
Met
hylt
hioe
thyl
amin
e9.
18N
,N-D
imet
hylm
etho
xyam
ine
3.65
2-th
ieny
lmet
hyla
min
e8.
92T
riam
inot
riet
hyla
min
e8.
56,
9.59
,10
.29
Ref
. 5M
ethy
l-[β
-die
thyl
amin
o-et
hyl]
sulf
ide
9.8
N-D
imet
hyl-
cyst
eam
ine
7.95
, 10.
7N
-Die
thyl
-cys
team
ine
7.8,
10.
75N
-Dip
ropy
l-cy
stea
min
e8.
00, 1
0.8
N-β
-Mer
capt
oeth
yl-p
iper
idin
e7.
95, 1
1.05
N-β
-Mer
capt
oeth
yl-m
orph
olin
e6.
65, 9
.81-
Die
thyl
amin
o-pr
opan
- (3)
8.0,
10.
51-
Die
thyl
amin
o-bu
tan-
(4)
10.1
1-D
ieth
ylam
ino-
hexa
n- (6
)10
.1
AN
ILIN
ES
(R
ef. 8
8)
m-S
ub
stit
ute
d a
nil
ines
m-C
2H5
4.70
m-C
H(C
H3)
24.
67 -
C(C
H3)
34.
663,
5-(C
H3)
24.
743,
5-[C
(CH
3)3]
24.
97m
-CO
CH
33.
56m
-CN
2.76
3-C
l,5-O
CH
33.
103-
OC
H3.
5-N
O2
2.11
3,5-
(OC
H3)
23.
823,
5-B
r 22.
34
NA
PH
TH
AL
AM
INE
S(r
efer
ence
88)
sub
stit
ute
d n
aph
thal
amin
es2-
nap
hth
alam
ine
X4.
162-
nap
hth
alam
ine
X1-
NH
2,3-
XN
O2
2.07
2-N
H2,
4-X
NO
22.
43C
N2.
26C
N2.
66C
l2.
66C
l3.
38B
r2.
67B
r3.
40I
2.82
I3.
41C
OO
CH
33.
12C
OO
CH
33.
38O
CH
33.
26O
CH
34.
05O
H3.
301-
NH
2,6-
XN
O2
2.89
CH
33.
96C
l3.
48C
l2.
71O
CH
33.
902-
NH
2,5-
XN
O2
3.01
OH
3.97
OH
4.07
2-N
H2,
7-X
NO
23.
101-
NH
2,5-
XN
O2
2.73
Cl
3.71
OH
3.96
OC
H3
4.19
Cl
3.34
OH
4.25
NH
24.
21N
H2
4.66
1-N
H2,
7-X
NO
22.
552-
NH
2,6-
XN
O2
2.62
Cl
3.48
OC
H3
4.64
OC
H3
4.07
2-N
H2,
8-X
NO
22.
73O
H4.
201-
NH
2,4-
XN
O2
0.54
1-N
H2,
2-X
NO
2-1
.74
Br
3.21
1-X
,2-N
H2
NO
2-0
.85
2-N
H2,
3-X
NO
21.
481-
NH
2,8-
XN
O2
2.79
,
An
ilin
es (
in 5
0% e
than
ol)
5'-I
MP
8.9,
1.5
4, 6
.04
6U
nh
ind
ered
pK
ref.
5-M
ethy
lcyt
osin
e4.
6, 1
2.4
6A
nil
ine
4.19
405-
Met
hylc
ytos
ine
deo
xyri
bosi
de
5'-p
hosp
hate
4.4
6p
-Am
inod
iphe
nyl
3.81
402-
Nap
hth
yla
min
e3.
7740
3-M
ethy
lura
cil
9.75
373-
Ph
enan
thry
lam
ine
3.59
403-
Met
hylx
anth
ine
8.5
(8.1
), 11
.338
m-A
min
odip
heny
l3.
8240
Ad
enos
ine
3.63
62-
Am
inof
luor
ene
4.21
40
"3.
3, 1
2.5
352-
Ph
enan
thry
lam
ine
3.60
405'
-AM
P3.
3, 6
.136
2-A
nth
ryla
min
e3.
4040
3.74
, 6.2
-6.4
6H
ind
ered
Barb
ituri
c ac
id3.
9, 1
2.5
37o-
Am
inod
iphe
nyl
3.03
40C
ytid
ine
4.11
6p
eri
"
4.22
, 12.
535
1-N
aph
thy
lam
ine
3.40
402'
-CM
P4.
3-4.
4, 6
.19*
69-
Ph
enan
thry
lam
ine
3.19
405'
-CM
P4.
5, 6
.36
3-A
min
opyr
ene
2.91
40C
TP
4.6,
6.4
61-
Ph
enan
thry
lam
ine
3.23
402,
6-D
iam
inop
urin
e5.
09, 1
0.77
61-
An
thry
lam
ine
3.22
40Is
ogua
nine
4.51
, 8.9
96
Gua
nosi
ne (d
eoxy
)1.
6-2.
2, 9
.16-
9.5
6m
eso
GM
P (2
' + 3
')2.
3, 9
.36,
0.7
, 5.9
69-
An
thry
lam
ine
2.7
405'
-GM
P (d
eoxy
)2.
9, 9
.7, 6
.46
o-A
min
oph
enol
sG
TP
3.3,
9.3
, 6.5
63-
Hyd
roxy
anth
ran
ilic
aci
d10
.09,
5.2
051
Inos
ine
1.2,
8.9
62-
Am
inop
heno
l hyd
roch
lori
de
"
8.75
, 12.
56
9.99
, 4.8
651
5-M
ethy
lcyt
osin
e d
eoxy
ribo
sid
eIn
dic
ator
sp-
Am
inoa
zobe
nzen
e2.
82, 2
.76
604.
5, 1
3.0
64-
Ch
loro
-2-n
itro
anil
ine
-1.0
2, -
1.03
601-
Met
hylu
raci
l9.
9537
4,6-
Dic
hlo
ro-2
-nit
roan
ilin
e -
3.61
, -3.
3260
1-M
ethy
lxan
thin
e7.
7, 1
2.05
386-
Bro
mo-
2,4-
din
itro
anil
ine
-6.6
4, -
6.71
7-M
ethy
lxan
thin
e8.
5 (8
.3)
382-
Am
ino-
4,5-
dim
eth
ylp
hen
ol h
ydro
chlo
rid
e10
.40,
5.28
519-
Met
hylx
anth
ine
6.3
38Pu
rine
2.52
, 8.9
037
N,N
-Dim
eth
yl-2
,4-d
init
roan
ilin
e -1
.00,
--
60T
hym
idin
e9.
86
p-N
itro
dip
hen
ylam
ine
5'-T
MP
10.0
, 1.6
, 6.5
6-2
.4 t
o -2
.9, -
2.50
60U
raci
l deo
xyri
bosi
de
9.3
64-
Met
hyl
-2,
din
itro
anil
ine
-3.9
6, -
4.44
605'
-UM
P9.
5, 6
.46
Het
eroc
ycli
csU
TP
9.5,
6.6
6N
ucl
eosi
des
, etc
.U
ridi
ne9.
256
Ad
enin
e4.
15, 9
.80
6
"9.
17, 1
2.5
352'
-AM
P3.
81, 6
.17
6X
anth
osin
e0,
5.5
, 13.
06
3'-A
MP
3.74
, 5.9
26
Oro
tic a
cid
2.8,
9.4
5, 1
36
AD
P3.
95, 6
.336
Pyri
mid
ine
1.30
37A
TP
4.00
(4.1
), 6.
536
Thy
min
e0,
9.9
, 713
.06
Bar
bita
l7.
85, 1
2.7
37U
raci
l.5
, 9.5
, 13.
06
Cyt
osin
e4.
45, 1
2.2
6U
MP
(2' +
3')
9.43
, 1.0
2, 5
.88
6C
ytos
ine
(deo
xy)
4.25
6U
DP
9.4,
6.5
63'
CM
P4.
16-4
.31,
6.0
46
Uri
c ac
id5.
4, 1
0.3
6C
DP
4.44
6X
anth
ine
0.8,
7.4
4, 1
1.12
6C
DP,
(deo
xy)
4.8,
6.6
6
"7.
238
Gua
nine
3.3,
9.2
, 12.
36
Gua
nosi
ne2.
2, 9
.56
"
1.6,
9.1
6, 1
2.5
355'
-GM
P2.
4, 9
.4, 6
.16
GD
P2.
9, 9
.6, 6
.36
Hyp
oxan
thin
e1.
98, 8
.94,
12.
106
Het
eroc
yclic
Bas
es
(Ref
. 2)
NN
NN
NN
N
N
NN
N
NN
N
N
NN
NN
NN
N
N
NN
Pyr
idin
e 5.
14*
pK (2
0°)
235
46 7
8
Qui
nolin
e 4.
85*
Isoq
uino
line
5.14
*B
enzo
quin
olin
e 5.
05*
234
56
7 8
910
1
Acrid
ine
5.60
5,6-
Benz
oqui
nolin
e5.
15*
7,8-
Benz
oqui
nolin
e4.
25*
Phen
anth
ridin
e 3.
30a
2,3-
Benz
acrid
ine
4.52
a3,
4-B
enza
crid
ine
4.70
*1,
2-Be
nzac
ridin
e 3.
45a
Pyr
idaz
ine
2.10
*P
yrim
idin
e 1.
10*
Pyr
azin
e 0.
37*
Cin
nolin
e 2.
64*
Phth
alaz
ine
3.39
*Q
uina
zolin
e 3.
31*
Qui
noxa
line
0.6*
a 50
% E
tOH
Het
eroc
ycli
cs3-
Hyd
roxy
8.81
, 5.5
239
Aur
eom
ycin
3.30
, 7.4
4, 9
.27
775-
Hyd
roxy
(acr
idon
e)--
f, -0
.32
39Ir
idin
e--
, 5.6
239
5-M
etho
xy--
, 739
Acr
idin
e1-
-2-
-3-
-4-
-5-
-9-
-R
ef. 2
H--
5.60
*4.
11a
H2N
--4.
40*
8.04
*5.
88*
6.04
*9.
99*
3.59
a7.
61a
5.03
a5.
50a
9.45
a
HO
--4.
18a
4.86
a5.
5239
4.45
a-.3
239
10.7
a9.
9a8.
8139
9.4*
>12
CH
3--
3.95
a4.
60a
4.70
a
H2K
-(1-
CH
3--)
--4.
79a
9.73
s3.
22a
1,9-
(CH
3)2-
-2.
88a
a 50
% e
than
ol; r
ef. 3
98-
amin
o-1,
2-be
nzac
rid
ine
6.72
40α
,α'-d
ipyr
idyl
4.43
62-
amin
o-4-
met
hyl-
5,6-
benz
oqu
inol
ine
7.14
404-
amin
o-8.
75a
194-
amin
o-2-
met
hyl-
9.45
a19
3-am
ino-
6,7-
benz
oqui
nolin
e 4.
7840
4-am
ino-
2-m
ethy
l-8-
chlo
ro- 5
.95a
198-
amin
o-3,
4-be
nzac
rid
ine
7.42
408-
chlo
ro-
2.5a
191'
-am
ino-
5,6-
benz
oqu
inol
ine
5.03
403,
4-d
iam
ino-
8.15
a19
4'-a
min
o-5,
6-be
nzoq
uin
olin
e 5.
2040
3-am
ino-
4.78
, 3.7
3a19
2-am
ino-
4-m
ethy
l-7,
8,be
nzoq
uin
olin
e7,
8-be
nzqu
inol
ine
4.25
, 3.1
5a19
6.74
404-
amin
o-7.
68a
196,
7-be
nzoq
uino
line
5.05
, 3.8
4a19
4-am
ino-
2-m
ethy
l-7.
96a
195,
6-be
nzoq
uino
line
5.15
, 3.9
0a19
2-am
ino-
4-m
ethy
l-6.
74, 6
.02a
194-
amin
o-7.
99a
196-
amin
o-2-
met
hyl-
5.23
a19
2-m
ethy
l-4.
44a
191'
-am
ino-
2-m
ethy
l-4.
75a
194-
amin
o-2-
met
hyl-
8.45
a19
3,4-
benz
acri
din
e4.
70, 4
.16a
192-
amin
o-4-
met
hyl-
7.14
, 6.5
1a19
5-am
ino
8.41
a19
4'-a
min
o-5.
20, 4
.10a
197-
amin
o-5.
03a
193'
-am
ino-
4.02
a19
8-am
ino-
7.42
(6.5
1)a
191'
-am
ino-
5.03
198-
acet
amid
o-4.
48a
192'
,4'-d
iam
ino-
4.91
a19
8-d
imet
hyla
min
o-7.
31, 6
.99
19B
enzi
min
azol
e5.
5319
1,2-
benz
acri
din
e3.
45a
192-
amin
o-7.
5419
5-am
ino-
8.13
a19
Ben
ztri
azol
e1.
619
7-am
ino
4.05
a19
Ben
zthi
azol
e1.
2, 0
.1a
198-
amin
o-6.
72, 5
.97a
192-
amin
o-4.
5119
4',5
-dia
min
o-8.
44a
19be
nzox
azol
e(d
ecom
p.)
192-
amin
o-3.
7319
Cin
nolin
e--
, 0.2
139
2,3-
benz
acri
din
e4.
52a
193-
hyd
roxy
8.64
, 0.2
139
5-hy
dro
xy7.
40, 1
.92
395-
amin
o-9.
72a
197-
hyd
roxy
7.56
, 3.3
139
5-ac
etam
ido-
4.56
a19
4-m
etho
xy--
, 3.2
139
7-am
ino-
5.38
a19
5-am
ino-
6:7:
8:9-
tetr
ahyd
ro- 9
.66a
19H
eter
ocyc
lics
Caf
fein
e0.
614
o,o'
-dip
yrid
yl4.
436
cinc
honi
ne7.
24
hyd
anto
in9.
1642
Cin
nolin
e2.
7019
5-is
opro
pyl-
2-th
io-
8.70
424-
amin
o-6.
8419
5,5-
pent
amet
hyle
ne2-
thio
8.79
42C
ocai
ne7.
64
3,5,
5-tr
imet
hyl-
2-th
io10
.80
42C
inno
line
4-hy
dro
xy9.
27, 0
.35
393-
met
hyl-
5,5-
pen
tam
ethy
lene
-2-t
hio-
6-hy
dro
xy7.
52, 3
.65
3911
.23
42-h
ydro
xy8.
20, 2
.74
39Im
idaz
oles
2-M
ethy
limid
azol
e7.
7543
His
tidin
em
ethy
lest
er5.
2 (N
H2
7.1)
43N
-Ace
tylh
istid
ine
7.05
432-
Met
hyl-
4-hy
dro
xy-a
min
oben
z- 6
.65
434-
Hyd
roxy
met
hyl-
6.45
432-
Met
hyl-
4-hy
dro
xy-6
-nit
ro-b
enzi
mid
azol
e3.
943
2-M
ethy
lben
z-6.
143
His
tam
ine
6.0
434-
Hyd
roxy
-6-N
itro
benz
-3.
0543
4-H
ydro
xy-6
-am
inob
enz-
5.9
43b 2
-Hyd
roxy
met
hyln
apht
h(1,
2)-
4-H
ydro
xybe
nz-
5.3
(OH
9.5
)43
4.44
, 12.
2386
4-M
etho
xybe
nz-
5.1
43b 2
-Hyd
roxy
met
hyln
apht
h(2,
3)-
4-B
rom
o-3.
743
4.50
, 12.
2386
6-N
itro
benz
-3.
05, 1
0.6
434-
Hyd
roxy
-4.
80, 8
.68
444-
Nit
ro-
1.5,
9.1
431-
Am
ino-
7.62
40is
oQu
inol
ines
4-A
min
o-6.
2840
1-H
ydro
xy-
-1.2
446-
Am
ino-
7.17
405-
Hyd
roxy
5.40
, 8.4
544
8-A
min
o-6.
0640
3-A
min
o-5.
0540
7-H
ydro
xy-
5.70
405-
Am
ino-
5.59
401-
Met
hoxy
-3.
0544
Am
ino-
6.20
404-
NO
21.
3588
6-H
ydro
xy-
5.85
, 9.1
544
4-B
r3.
3188
8-H
ydro
xy-
5.66
, 8.4
044
1-H
ydro
xy-
--, 1
.44
392-
Met
hylis
oqui
nolo
ne-1
.844
5-M
ethy
l-1-
phen
azon
e--
, 4.9
39Is
oqui
nolin
e5.
46, 5
.14
44, 1
9m
-Phe
nant
hrol
ine
3.11
a19
Phen
azin
e--
, 1.2
339
1-A
min
o-ca
. 7.3
, 7.2
9a19
2-H
ydro
xy-
7.5,
2.6
392,
2'-D
ipyr
idyl
4.23
1910
-Met
hyl-
2-ph
enaz
one
--, 3
.02-
Hyd
roxy
-8.
79, 4
.82
446-
Am
inop
hena
nthr
idin
e6.
8840
7-H
ydro
xy-
4.38
, 8.6
844
9-A
min
ophe
nant
hrid
ine
7.31
409-
Met
hoxy
---
, 2.3
844
o-Ph
enan
thro
line
4.27
a , 5
.219
2-A
min
o-9-
met
hyl-
5.66
a19
p-Ph
enan
thro
line
3.12
a19
2,7-
Dia
min
o-9-
met
hyl-
6.26
a19
1,10
-Dia
min
o-3,
8-D
imet
hyl-
8.7
8a, 6
.31a
6-A
min
o-6.
8840
Phen
azin
e1.
2319
Phen
anth
rid
ine
--, 4
.65
441-
Am
ino-
2.6a
196-
Hyd
roxy
-8.
43, 5
.35
442-
Am
ino-
4.75
, 3.4
6a19
9-H
ydro
xy (p
hena
nthr
idon
e) <
-1.5
441,
3-D
iam
ino-
5.64
a19
9-A
min
o-7.
31, 6
.75a
192,
3-D
iam
ino-
4.74
192,
7,9-
Tri
amin
o-8.
06a
192,
7-D
iam
ino-
4.63
, 3.9
a19
Phth
alaz
ine
3.47
19Pt
eroy
lglu
tam
ic a
cid
8.26
771-
Am
ino-
6.60
191-
Hyd
roxy
-11
.00,
-239
Pyr
idin
esPi
colim
ic a
cid
5.52
42-
Am
ino-
6.86
415,
5-d
imet
hyl-
2-th
io-
8.71
424-
Am
ino-
9.17
415,
5-D
iphe
nyl-
2-th
io-
7.69
422-
Met
hyl-
5.94
b45
1-M
ethy
l-5,
5-pe
ntam
ethy
l-en
e-2-
thio
-2-
Vin
yl-
4.98
459.
2542
2-C
hlor
o-0.
4945
4-M
ethy
l-7.
4543
2,4,
6-T
rihy
dro
xy-
4,6,
9.0
, 13
39Im
idaz
ole
6.95
431-
Met
hyl-
4-py
rid
one
3.33
4-(2
',4'-D
ihyd
roxy
phen
yl)-
6.45
432-
(N-M
ethy
lace
tam
ido)
-2.
0146
Car
bobe
nzox
y-L
-his
tid
yl-L
-tyr
osin
e et
hyl
este
r6.
2543
2-B
enza
mid
o-3.
332-
(N-M
ethy
lben
zam
ido)
-1.
446-
Am
inob
enz-
6.0
(NH
2 3.
0)3-
(N-M
ethy
lace
tam
od)-
3.52
46B
enzi
mid
azol
e5.
443
3-(N
-Met
hylb
enza
mid
o)-
3.66
464-
(N-M
ethy
lace
tam
ido)
-4.
6246
4-(N
-Met
hylb
enza
mid
o)-
4.68
46(C
H3)
2CH
-5.
83b
5.72
b 6
.02b
4-B
enza
mid
o-5.
3246
CH
3CO
3.18
b3-
NO
20.
8188
H2N
-6.
68b
5.80
b 8
.96b
3-C
OO
–4.
7747
CO
NH
2473.
40 3
.61
2,3-
Me 2
6.60
48N
C-4
71.
452,
5-M
e 26.
4748
3,4-
Me 2
6.52
482,
4,6-
Me 3
7.48
484-
OE
t6.
6748
3-C
l2.
8448
3-C
O2E
t3.
3548
3-C
OO
H3.
1388
2-A
myl
-6.
00b
452-
Hex
yl-
5.95
b45
2-B
enzy
l-5.
1345
2-B
rom
o-0.
7145
2,4-
Dih
ydro
xy6.
50, 1
3, 1
.37
391-
Met
hyl-
2-py
rid
one
0.32
392-
Ace
tam
ido-
4.09
461-
Met
hylp
yrid
-2-o
ne a
cety
limin
e 7.
1246
3-A
ceta
mid
o-4.
4646
3-B
enza
mid
o-3.
8046
1-M
ethy
lpyr
id-4
-one
ace
tylim
ine
11.0
346
1-M
ethy
lpyr
id-4
-one
ben
zylim
ine
9.89
464-
CO
O–
4.90
472,
4-M
e 26.
7248
2,6-
Me 2
6.77
483,
5-M
e 26.
1448
2-M
e,5-
Et
6.51
483-
F3.
1048
3-B
r2.
8448
4-C
O2E
t3.
4548
Pyr
idin
e N
-oxi
des
(see
oxy
gen
acid
s)
Su
bst
itu
ted
Pyr
idin
esP
yrid
ine
2-3-
4-H
-5.
17b
Cl-
0.72
b2.
84b
I-1.
82b
3.25
b
CH
3CH
2-5.
97b
5.70
b6.
02b
(CH
3)3C
-5.
76b
5.82
b5.
99b
HO
-0.
754.
863.
2711
.62
8.72
11.0
9SO
3-47
2.9
CH
3O-
3.28
4.88
6.62
F--0
.44b
2.97
b
Br-
0.90
b2.
84b
CH
3-5.
97b
5.68
b 6
.02b
Ort
ho-
Su
bst
itu
ted
Pyr
idin
es (i
n 50
% e
than
ol)
Pyri
daz
ine
2.33
19S
ub
stit
uen
tp
Kre
f.3-
Hyd
roxy
-10
.46,
-1.8
39H
-4.
382
3,6-
Dih
ydro
xy-
5,67
, -2.
2, 1
339
2-C
2H5-
4.93
24-
Met
hoxy
-3.
7039
3-A
min
o-5.
1919
2-(C
H3)
4.68
24-
Hyd
roxy
-8.
68, 1
.07
392,
6-[(
CH
3)2C
H] 2
3.58
23-
Met
hoxy
-2.
5239
2-(C
H3)
3C-
4.68
23,
6-D
imet
hoxy
-1.
6139
2-C
2H5-
6-(C
H3)
3C-
4.36
22,
6-[(
CH
3)3C
] 2–
3.58
2Fo
r co
mpl
ex c
hela
ting
age
nts,
see
als
o re
f. 77
2-C
H3-
5.05
2b
ther
mod
ynam
ic a
t 25°
.2-
(CH
3)2C
H-
4.82
22,
6-(C
H3)
25.
772
2,6-
[(C
H3)
3C] 2
3.58
22-
CH
3-6-
(CH
3)3C
5.52
22-
(CH
3)2C
H-6
-(C
H3)
3C-
5.13
2
pK
NH
35°
pK
OH
Ben
zim
idaz
ole
6.00
5.58
5.36
2-M
ethy
l6.
966.
296.
18--
-2-
Eth
yl6.
906.
276.
14--
2-H
ydro
xym
ethy
l--
-5.
40--
-11
.55
ref.
861-
Met
hyl-
2-hy
dro
xym
ethy
l--
-5.
55--
-11
.45
2,4-
Dih
ydro
xy-(
Ura
cil)
9.38
, 12
394,
6-D
ihyd
roxy
-5.
439
2,4,
6-T
rihy
dro
xy-(
Bar
bitu
ric
acid
)O
ther
(ref
. 95)
3.9,
12.
539
Thia
zolid
ine
6.31
2-M
etho
xy-
<1
39M
ethy
l thi
azol
idin
e-4-
carb
oxyl
ate
4.00
4-M
etho
xy-
2.5
39Th
iazo
lidin
e-4-
CO
OH
1.51
, 6.2
11-
Met
hyl-
2-py
rim
idon
e2.
5039
3-M
ethy
l-4-
pyri
mid
one
1.84
39(r
ef. 9
6)4-
Am
ino-
5.71
192-
Met
hyl-Δ2
-oxa
zolin
e5.
52-
Am
ino-
4-m
ethy
l-4.
1519
2,4-
Dia
min
o-7.
2619
4-C
arba
moy
l-2-
phe
nyl-Δ2
-oxa
zolin
e2.
94-
Met
hyl-
1.98
192-
Phen
yl-Δ
2 -ox
azol
ine
4.4
4-H
ydro
xy-
8.59
, 1.8
539
4,5-
Dih
ydro
xy-
7.48
, 1.9
9, 1
1.61
39H
eter
ocyc
lics
2,4,
5-T
rihy
dro
xy-(
isoB
arbi
turi
c ac
id)
Pyr
azin
esp
Kre
f.8.
11, 1
1.48
39Py
razi
ne1.
1, 0
.649
, 39
4-H
ydro
xy-5
-met
hoxy
-8.
601.
7539
2,5-
Dim
ethy
l-2.
149
2,3,
5,6-
Tet
ram
ethy
l-2.
849
1-M
ethy
l-4-
pyri
mid
one
1.8
392-
Met
hoxy
---
, 0.7
539
2-M
ethy
l-1.
549
Mis
cell
aneo
us
2,6-
Dim
ethy
l-2.
549
4-H
ydro
xy-2
-met
hylp
yrid
azin
ium
chl
orid
e1.
7444
2-H
ydro
xy-
8.23
, 0.1
391-
Met
hyl-
2-py
razi
ne-0
.04
398-
Hyd
roxy
-6-m
ethy
l-1,
6-na
phth
yrid
iniu
mch
lori
de
4.34
442-
Am
ino-
3.14
19Py
rim
idin
e1.
3019
2-H
ydro
xyph
enaz
ine
2.6
442-
Am
ino-
3.54
194-
Hyd
roxy
pter
idin
e-0
.17
445-
Am
ino-
2.83
193-
Met
hyl-
4-pt
erid
one
-0.4
744
2-A
min
o-4,
6-d
imet
hyl-
4.85
195-
Hyd
roxy
pyri
mid
ine
1.87
, 6.7
844
2,4,
6-T
riam
ino-
6.84
198-
Hyd
roxy
-1,6
-Nap
hthy
rid
ine
4.08
442-
Hyd
roxy
-9.
17, 2
.24
391-
Hyd
roxy
phen
azin
e1.
4444
5-M
ethy
l-1-
phen
azon
e4.
944
10-M
ethy
l-2-
phen
azon
e3.
044
1-M
ethy
l-4-
pter
idon
e1.
2544
Qu
inol
ine
2--
34
56
78
Ref
.H
-4.
85*
4.80
4.69
*2
H2N
-7.
25*
4.86
*9.
08*
5.37
*5.
54*
6.56
*3.
90*
2H
O-
-.36
4.30
2.27
5.20
5.17
5.48
5.13
4411
.74
8.06
11.2
58.
548.
888.
859.
8944
CH
35.
425.
145.
204.
624.
925.
084.
602
5.8
5.6
5.2
5.0
2F-
2.36
*3.
68*
4.00
*4.
04*
3.08
*2
Cl-
3.73
*2
HO
2C4.
96*
4.62
*4.
53*
4.81
*4.
98*
4.97
*7.
20*
2N
O2
1.03
88
5-H
ydro
xy-1
-met
hylq
uiox
alin
ium
chl
orid
e5.
7444
Qu
inol
ine
2,4-
Dih
ydro
xy-
5.86
, 0.7
639
Rib
ofla
vin
9.93
774-
Met
hoxy
-6.
6559
Sulp
hadi
azin
e6.
486
1-M
ethy
l-4-
quin
olon
e2.
4639
Sulp
hapy
ridi
ne8.
436
2,4-
Dia
min
o-9.
4519
2-A
min
othi
azol
e5.
3941
Qu
inaz
olin
e3.
51, 3
.2a
191,
3,5-
Tri
azin
e--
392,
4-D
ihyd
roxy
-6.
539
2-A
min
o-4.
4319
1,4,
6-T
riaz
anap
htha
lene
2.5
396-
Am
ino-
3.2a
194-
Hyd
roxy
-11
.05,
0.7
839
2-H
ydro
xy-
10.6
9, 1
.30
395-
Am
ino-
2.62
196-
Hyd
roxy
-8.
19, 3
.12
392,
3-D
iam
ino-
4.70
193-
Met
hiod
ide
7.26
395-
Hyd
roxy
-8.
65, 0
.939
2-M
etho
xy-
1.31
396-
Hyd
roxy
-7.
92, 1
.40
392-
Met
hoxy
-3.
1739
1,5-
Nap
hthy
rid
ine
2.91
391-
Met
hyl-
2-qu
inol
one
-0.7
139
4-H
ydro
xy10
.01,
2.8
539
4-A
min
o-9.
44, 9
.17
19, 4
1Su
lpha
quan
idin
e11
.25
68-
Qui
nolin
ol5.
13, 9
.89
6Su
lpha
thia
zole
7.12
63-
Cl
--, 2
.46
88, 4
4T
erra
myc
in3.
10, 7
.26,
9.1
177
3-B
r2.
6188
4-A
min
o-5.
7319
Tet
ram
ethy
lene
dia
min
e10
.74
8-A
mon
o-2.
4a19
1,4,
5-T
riaz
anap
htha
lene
1.20
394-
Hyd
roxy
-9.
81, 2
.12
398-
Hyd
roxy
-8.
76, 0
.60
398-
Hyd
roxy
-8.
65, 3
.41
392,
4-D
ihyd
roxy
-9.
78, 2
.539
4-M
etho
xy-
3.13
39S
PE
CIA
L N
ITR
OG
EN
CO
MP
OU
ND
S*T
herm
odyn
amic
Hyd
roxy
lam
ines
Hyd
roxy
lam
ine
5.97
*12
Het
eroc
ycli
csN
-Met
hyl-
5.96
*12
Qu
inox
alin
e0.
8, 0
.56
19, 3
9O
-Met
hyl-
4.60
*12
2-A
min
o-3.
9619
Tri
met
hyl-
3.65
*12
6-A
min
o-2.
9519
N-D
imet
hyl-
5.20
*12
2-H
ydro
xy-
9.08
, -1.
3739
N,O
-Dim
ethy
l-4.
75*
121-
Met
hiod
ide
5.74
392,
3-D
ihyd
roxy
-9.
5239
Hyd
razi
nes
(30°
)Ph
enyl
guan
idin
e10
.88
19H
ydra
zine
8.07
13B
enza
mid
ine
11.6
19M
ethy
l-7.
8713
N-P
heny
l-O
-met
hylis
oure
a 7.
320
N,N
'-Dim
ethy
l-7.
5213
Tet
ram
ethy
l-6.
3013
N,N
-Die
thyl
-7.
7113
Nit
roge
n c
omp
oun
ds,
mis
cell
aneo
us
Phen
yl-
5.21
(15°
)14
Dig
uani
de--
3.07
, 13.
2577
Gly
cylh
ydra
zide
2.38
, 7.6
915
Dit
hioo
xam
ide
(rub
eani
c ac
id,
N,N
-Dim
ethy
l-7.
2113
H2N
CSC
SNH
2)10
.62
77T
rim
ethy
l-6.
5613
Eth
ylen
edig
uani
de
Eth
yl-
7.99
131.
74, 2
.88,
11.
34, 1
1.76
77N
,N'-D
ieth
yl-
7.78
13Ph
enyl
digu
anid
e2.
16, 1
0.71
77A
cet-
3.24
15Is
onic
otin
hyd
razi
de
1.85
, 3.5
4, 1
0.77
77O
ther
S-M
ethy
lisot
hiou
rea
9.83
20H
ydra
zon
es H
ydra
zone
of:
N-P
heny
l-S-
met
hylis
othi
oure
a 7.
1420
Ben
zop
heno
ne3.
8516
p,p'
-Dim
etho
xy-
4.38
16p-
Chl
oro-
4.38
16C
inch
ona
Alk
aloi
ds
(in
80%
aqu
eous
met
hyl
cello
solv
e)p
-Met
hoxy
acet
ophe
none
4.94
16p,
p'-D
ichl
oro-
3.13
16Q
uini
ne7.
732
Phen
yl-2
-thi
enyl
ket
one
3.80
16Q
uini
dine
7.95
2E
phed
rine
9.14
2S
emic
arb
azon
es o
f:N
-Met
hyle
phed
rine
8.50
2Se
mic
arba
zid
e3.
66Ep
iqui
nine
8.44
2Fu
rfur
al1.
4414
Epiq
uini
dine
8.32
2B
enza
ldeh
yde
0.96
14ψ
-Eph
edri
ne9.
222
Ace
tone
1.33
14N
-Met
hyl-ψ
-eph
edri
ne8.
812
Ace
tald
ehyd
e1.
1014
Pyru
vic
acid
0.59
14A
ceta
mid
e-0
.51
4U
rea
0.18
4T
hiou
rea
-0.9
64
Am
idox
imes
Ox-
3.02
17B
enz-
4.99
17T
hio
lsα
-Phe
nyla
cet-
5.24
17N
-Dim
ethy
l-cy
stea
min
e7.
95, 1
0.7
7Su
ccin
-3.
11, 5
.97
17N
-Dip
ropy
l-cy
stea
min
e8.
00 1
0.8
5o-
Tol
u-4.
0317
N-β
-Mer
capt
oeth
yl-m
orph
olin
e 6.
65, 9
.8p-
Tol
u-5.
1417
1-D
ieth
ylam
ino-
buta
n- (4
)10
.15
Mal
on-
~4.
7717
Met
hyl-
[β-d
ieth
ylam
ino-
ethy
l]-s
ulfi
de
9.8
5O
ther
Met
hyl t
hiog
lyco
late
7.8
23D
iphe
nylt
hioc
arba
zone
4.5
6M
erca
ptoe
thyl
amin
e8.
6, 1
0.75
23Ph
thal
imid
e8.
3018
N-t
rim
ethy
l cys
tein
e8.
623
Nit
rour
etha
ne3.
2818
Glu
tath
ione
2.12
, 3.5
9, 8
.75,
9.6
523
Ace
tylg
uani
dine
8.33
19N
-Die
thyl
-cys
team
ine
7.8,
10.
755
Ace
tam
idin
e12
.52
19N
-Β-M
erca
ptoe
thyl
-pip
erid
ine
O-M
ethy
lisou
rea
9.80
207.
95, 1
1.05
5D
imed
one
5.23
181-
Die
thyl
amin
o-pr
opan
- (3)
8.0
, 10.
55
Nit
rour
ea4.
5718
1-D
ieth
ylam
ino-
hexa
n- (6
)10
.15
Gua
nidi
ne13
.71
19
p-N
itro
benz
enet
hiol
5.1
58o-
Mer
capt
o-ph
enyl
acet
ic a
cid
Thio
glyc
olic
aci
d3.
67, 1
0.31
234.
28, 7
.67
59M
erca
ptoe
than
ol9.
523
Eth
yl m
erca
ptan
10.5
081
Cys
tein
e1.
8, 8
.3, 1
0.8
23I-
Thi
o-D
-sor
bito
l9.
3591
Cys
tein
ylcy
stei
ne2-
mer
capt
oeth
anes
ulf
onat
e 7.
53 (9
.1)
812.
65, 7
.27,
9.3
5, 1
0.85
23o-
amin
othi
ophe
nol
6.59
81T
hiop
heno
l8.
20a ,
7.8
, 6.5
2
59,
81,
82
Β-M
erca
ptop
ropi
onic
aci
d 1
0.27
81X
=-H
-S–
-SH
Met
hyl c
yste
ine
6.5
(7.5
)81
X(C
H2)
2SH
12.0
13.9
610
.75
X(C
H2)
4SH
12.4
13.2
511
.50
p-C
l-th
ioph
enol
7.50
81X
(CH
2)3S
H13
.24
11.1
4M
erca
pta
ns,
RS
HX
(CH
2)5S
H13
.27
11.8
2R C
H3C
CH
2-7.
8632
C6H
5CH
2-9.
4382
HO
CH
2CH
(OH
)CH
2-9.
5182
CH
2=C
HC
H2-
9.96
82n-
C4H
9-10
.66
82t-
C5H
11-
11.2
182
C2H
5OC
OC
H2-
7.95
82C
2H5O
CH
2CH
2-9.
3882
HO
CH
2CH
(OH
)CH
2-9.
6682
n-C
3H7-
a10.
6582
t-C
4H9-
11.0
582
CA
RB
ON
AC
IDS
Dic
yano
met
hane
122
Ace
toni
trile
c. 2
524
Ace
tone
~20
24B
enzo
ylac
eton
e (a
nol)
8.23
24A
cety
lace
tone
8.95
24D
imet
hyls
ulfo
ne14
24D
iace
tyla
ceto
ne6
24N
itro
etha
ne8.
618
Hyd
rocy
anic
aci
d9.
2125
2-ni
trop
ropa
ne7.
7418
1-ni
trop
ropa
ne9
18T
ricy
anom
etha
nest
rong
24Sa
ccha
rin
1.6
18T
rini
trom
etha
nest
rong
24T
ri-m
ethy
lsu
lfon
yl-m
etha
ne s
tron
g24
Nit
rom
etha
nest
rong
25
Bis
-(-D
iket
ones
):[(R
CO
)(R
'CO
)CH
] 2C
HR
(in
50%
dio
xane
)(r
ef. 2
8)R
R'
R"
pK
pK
CH
3C
H3
(CH
2)5C
H3
11.3
312
.52
CH
3C
H3
C6H
511
.10
12.4
9C
H3
CH
32-
ClC
6H4
11.0
412
.73
CH
3C
H3
2-C
5H4N
9.80
12.4
6C
H3
CH
32-
CH
3OC
6H4
11.4
712
.44
CH
3C
H3
3,4-
CH
2O2C
6H3
11.3
912
.60
CH
3C
H3
3-C
5H4N
10.2
912
.63
CH
3C
H3
4-C
H3O
C6H
411
.62
12.6
1C
H3
CH
34-
(CH
3)2N
C6H
411
.50
12.4
5C
H3
CH
3OC
H2
C6H
511
.54
12.2
7C
H3
CH
3OC
H2
2-C
5H4N
10.9
512
.49
CH
3C
H3O
CH
24-
(CH
3)2N
C6H
412
.13
12.3
1C
H3
CH
3OC
H2
4-C
H3O
C6H
411
.74
12.4
9C
H3O
CH
2CO
CH
2CO
CH
39.
66(C
H3C
O) 2
CH
(CH
2)3C
H3
12.0
7
Bis
-(-D
iket
ones
) (R
CO
)-(R
'CO
)CH
-Y-C
H(C
OR
)(C
OR
') (i
n 50
% d
ioxa
ne)
(ref
. 26)
RR
'Y
pKpK
CH
3C
H3
9.43
13.5
4C
H3
CH
3(C
H2)
411
.99
12.4
8C
H3
CH
3(C
H2)
1012
.01
12.0
7C
H3
CH
31,
4-(C
H3)
2C6H
411
.27
12.1
5
Bis
-(-D
iket
ones
) RC
OC
H2C
O-Y
-CO
CH
2CO
R (i
n 75
% d
ioxa
ne)
(ref
. 26)
RY
pK
pK
C6H
5(C
H2)
412
.47
13.0
9C
6H5
(CH
2)5
12.7
213
.46
C6H
5(C
H2)
612
.60
13.4
6C
6H5
(CH
2)7
13.1
(est
.)C
6H5
(CH
2)3
12.5
813
.69
CH
3(C
H2)
512
.29
13.0
0C
H3=
CH
(CH
3)2
(CH
2)5
12.9
513
.60
CH
3NO
210
.29
74
CO
2Et
O10
.96
74
CH
3CH
ClN
O2
774
CH
3CO
CH
2 N
O2
5.1
74C
H(N
O2)
3st
rong
74
CH
3
OO
7.82
74
CH
3CO
CH
Cl 2
1574
CH
3CO
CH
C2H
5CO
2C2H
512
.774
CH
3CO
CH
CH
3CO
CH
311
74C
H3C
OC
H2C
OC
6H5
9.4
74D
init
rom
etha
ne4
2C
6H5C
OC
H2C
OC
F3
6.82
74Po
tass
ium
cya
nid
e9.
212
CH
3CO
CH
2CH
O5.
9274
CH
(CN
) 3st
rong
74C
H3
CO
CH
2 C
O2C
H3
1074
CH
2(C
O2C
2H5)
213
.374
CH
3SO
2CH
2SO
2CH
314
74C
H3C
O2H
~ 2
474
CH
3SO
2CH
(CO
CH
3)2
4.3
74O
Et
OO
10.5
74
C2H
5NO
28.
674
C2H
5O2C
CH
2 N
O2
5.82
74C
H2(
NO
2)2
3.57
74
O
CH
3
O10
.174
CH
3CO
CH
2Cl
c. 1
6.5
74C
H3C
OC
H2C
O2C
2H5
10.6
874
CH
3CO
CH
2CO
CH
39
74C
H3C
OC
HB
rCO
CH
37
74C
H2(
CH
O) 2
574
CH
3CO
CH
2CO
CF
34.
774
C6H
5CO
CH
2NC
5H5
10.5
174
CH
(CO
CH
3)3
5.85
74In
dic
ator
sC
H3S
O2C
H3
c. 2
374
Tro
peol
ine
OO
2.0
28C
H(S
O2C
H3)
3st
rong
74B
rom
ocre
sol g
reen
4.9
28C
H2(
CN
) 211
.81
74T
hym
ol b
lue
(1)
1.65
28C
2H5O
2CC
H2C
N9
74M
ethy
l ora
nge
3.45
28C
H3C
O2C
2H5
~ 2
4.5
74M
ethy
l yel
low
3.25
28C
HC
2H5(
CO
2C2H
5)2
1574
Neu
tral
red
7.4
28C
H3C
ON
H2
~ 2
574
Bro
mop
heno
l blu
e4.
128
S
OO
CF 3
6.10
74
Bro
mot
hym
ol b
lue
7.3
28T
hym
ol b
lue
(2)
9.2
28M
ethy
l red
(1)
2.3
28M
ethy
l red
(2)
5.0
28
Ref
eren
ces
1.H
all,
H.K
., Jr
. J. A
.m. C
hem
. Soc
.195
7,79
, 544
1.2.
Bro
wn,
H.C
. et
al.,
in
Bra
ude,
E.A
. an
d F
.C.
Nac
hod
Det
erm
inat
ion
of O
rgan
ic S
truc
ture
s by
Phy
sica
l Met
hods
, Aca
dem
ic P
ress
, New
Yor
k, 1
955.
3.H
all,
H.K
., Jr
. J. A
m. C
hem
. Soc
.195
7,79
, 543
9.4.
Han
dbo
ok o
f C
hem
istr
y an
d P
hysi
cs,
Ed
itor
in
Chi
ef,
Cha
rles
D.
hod
gman
, M
.S.;
Che
mic
alR
ubbe
r Pu
blis
hing
Com
pany
, Cle
vela
nd, O
H, 1
951,
p. 1
636-
7.5.
Fran
zen,
V. C
hem
. Ber
.195
7,90
, 623
.6.
Daw
son,
R.M
.C. e
t al.,
Dat
a fo
r B
ioch
emic
al R
esea
rch,
Oxf
ord
, Cla
rend
on P
ress
, 195
9.7.
Buis
t, G
.J.; L
ucas
, H.J.
J. A
m. C
hem
. Soc
.195
7,79
, 615
7.8.
Stev
enso
n, G
.W.;
Will
iam
son,
D. J
. Am
. Che
m. S
oc.1
958,
80, 5
943.
9.So
low
ay, S
.; L
ipsc
hitz
, H. J
. Org
. Che
m.1
958,
23, 6
13.
10.
Bis
sell,
E.R
.; Fi
nger
, M. J
. Org
. Che
m.1
959,
24, 1
256.
11.
Tuc
kerm
an, M
.M.;
May
er, J
.R.;
Nac
hod
, F.C
. J. A
m. C
hem
. Soc
.195
9,81
, 92.
12.
Bis
sot,
T.C
.; Pa
rry,
R.W
.; C
ampb
ell,
D.H
. J. A
m. C
hem
. Soc
.195
7,79
, 796
.13
.H
inm
an, R
.L. J
. Org
. Che
m.1
958,
23, 1
587.
14.
Con
ant,
J.B.;
Bar
tlet
t, P.
D. J
. Am
. Che
m. S
oc.1
932,
54, 2
881.
15.
Lin
deg
ren,
C.R
.; N
iem
ann,
C. J
. Am
. Che
m. S
oc.1
949,
71, 1
504.
16.
Har
nsbe
rger
, H.F
.; C
ochr
an, E
.L.;
Szm
ant,
H.H
. J. A
m. C
hem
. Soc
.195
5,77
, 504
8.17
.Pe
arse
, G.A
., Jr
.; Pf
laum
, R.T
. J. A
m. C
hem
. Soc
.195
9,81
, 650
5.18
.B
ell,
R.P
.; H
iggi
nson
, W.C
.E. P
ro. R
oyal
Soc
.194
9,19
7, 1
41.
19.
Alb
ert,
A.;
Gol
dacr
e, R
.; Ph
illip
s, J.
J. C
hem
. Soc
.194
8, 2
240.
20.
Dip
py, J
.F.J.
; Hug
hes,
S.R
.C.;
Roz
ansk
i, A
. J. C
hem
. Soc
.195
9, 2
492.
21.
Ed
sall,
J.T
.; M
arti
n, R
.B.;
Hol
lingw
orth
, B.R
. PN
'As
1958
,44,
505
.22
.M
arti
n, R
.B.;
Ed
sall,
J.T
.; W
etla
ufer
, D.B
.; H
ollin
gwor
th, B
.R. J
BC
1958
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