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Chemistry

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Diploma Programme

Chemistry data booklet
First examinations 2009

Diploma Programme
Chemistry data booklet

First published March 2007
Revised edition published September 2008
International Baccalaureate
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4019a

Contents

1. Some relevant equations

1

2. Physical constants and unit conversions

1

3. The electromagnetic spectrum

1

4. Names of the elements

2

5. The periodic table

3

6. Melting points and boiling points of the elements

4

7. First ionization energy, electron affinity and electronegativity of the elements

5

8. Atomic and ionic radii of the elements

6

9. Covalent bond lengths

7

10. Bond enthalpies and average bond enthalpies at 298 K

7

11. Organic compounds—thermodynamic data

8

12. Enthalpies of combustion

9

13. Lattice enthalpies at 298 K (experimental and theoretical values)

10

14. Standard electrode potentials

12

15. Strengths of organic acids and bases

13

16. Acid–base indicators

14

17. Infrared data

15

18. 1H NMR data

16

19. 2-Amino acids

17

20. Structural formulas of some medicines and drugs

19

21. Structural formulas of some biological molecules

21

22. Structural formulas of some food chemistry molecules

22

23. References

24

Notes
This booklet cannot be used for paper 1 of the examination (SLP1 and HLP1), but the periodic table given on page 3 will be available as part of these examination papers. Clean copies of this booklet must be made available to candidates for papers 2 and 3 (SLP2, SLP3, HLP2 and HLP3).

Chemistry data booklet

Chemistry data booklet

1. Some relevant equations log10 ln k = –

I0
= εlc
I

k = Ae

Ea
= ln A
RT

− Ea
RT

c=f λ

PV = nRT

∆G Ö = ∆H Ö − T ∆S Ö

q=mcΔT

E=hf

2. Physical constants and unit conversions
Avogadro’s constant (L) = 6.02 × 1023 mol–1
Gas constant (R) = 8.31 J K–1 mol–1
Molar volume of an ideal gas at 273 K and 1.01 × 105 Pa = 2.24 × 10 –2 m3 mol–1 (= 22.4 dm3 mol–1)
Planck’s constant (h) = 6.63 × 10 –34 J s
Specific heat capacity of water = 4.18 kJ kg–1 K–1 (= 4.18 J g–1 K–1)
Ionic product constant for water (Kw) = 1.00 × 10 –14 at 298 K
1 atm = 1.01 × 105 Pa
1 dm3 = 1 litre = 1 × 10 –3 m3 = 1 × 103 cm3

3. The electromagnetic spectrum
Energy
10 –16

10 –14

10 –12

γ rays

10 –10

10 –8

X rays

UV

10 –6

10 –4

IR

10 –2

microwaves

10 0

102

104

106

108

wavelength / m

radio waves

V I B G Y O R
400
700 wavelength / nm

Chemistry data booklet

1

Chemistry data booklet

4. Names of the elements
Element

Atomic number actinium aluminium americium antimony argon arsenic astatine barium berkelium beryllium bismuth bohrium boron bromine cadmium caesium calcium californium carbon cerium chlorine chromium cobalt copper curium dubnium dysprosium einsteinium erbium europium fermium fluorine francium gadolinium gallium germanium gold hafnium hassium helium holmium hydrogen indium iodine iridium iron krypton lanthanum lawrencium lead lithium lutetium magnesium manganese meitnerium

2

Symbol
Ac
Al
Am
Sb
Ar
As
At
Ba
Bk
Be
Bi
Bh
B
Br
Cd
Cs
Ca
Cf
C
Ce
Cl
Cr
Co
Cu
Cm
Db
Dy
Es
Er
Eu
Fm
F
Fr
Gd
Ga
Ge
Au
Hf
Hs
He
Ho
H
In
I
Ir
Fe
Kr
La
Lr
Pb
Li
Lu
Mg
Mn
Mt

89
13
95
51
18
33
85
56
97
4
83
107
5
35
48
55
20
98
6
58
17
24
27
29
96
105
66
99
68
63
100
9
87
64
31
32
79
72
108
2
67
1
49
53
77
26
36
57
103
82
3
71
12
25
109

Element mendelevium mercury molybdenum neodymium neon neptunium nickel niobium nitrogen nobelium osmium oxygen palladium phosphorus platinum plutonium polonium potassium praseodymium promethium protactinium radium radon rhenium rhodium rubidium ruthenium rutherfordium samarium scandium seaborgium selenium silicon silver sodium strontium sulfur tantalum technetium tellurium terbium thallium thorium thulium tin titanium tungsten uranium vanadium xenon ytterbium yttrium zinc zirconium

Symbol

Atomic number Md
Hg
Mo
Nd
Ne
Np
Ni
Nb
N
No
Os
O
Pd
P
Pt
Pu
Po
K
Pr
Pm
Pa
Ra
Rn
Re
Rh
Rb
Ru
Rf
Sm
Sc
Sg
Se
Si
Ag
Na
Sr
S
Ta
Tc
Te
Tb
Tl
Th
Tm
Sn
Ti
W
U
V
Xe
Yb
Y
Zn
Zr

101
80
42
60
10
93
28
41
7
102
76
8
46
15
78
94
84
19
59
61
91
88
86
75
45
37
44
104
62
21
106
34
14
47
11
38
16
73
43
52
65
81
90
69
50
22
74
92
23
54
70
39
30
40

Chemistry data booklet

Chemistry data booklet

7

6

5

4

3

2

1

12

39

38

37

223.02

226.03

Ra

88

87

Fr

137.33

132.91

Ba

56

Cs

87.62

55

Sr

85.47

Rb



Ac







227.03

89

138.91

La

57

88.91

Y

44.96

40.08

39.10

21

Sc

20

Ca

19

K

24.31

22.99

Mg

11

Na

9.01

4

Be

2

6.94

Li

3

1.01

H

1

1

Sg

232.04

231.04

238.03

U

92

91

Pa

90

Th

144.24

140.91

60

Nd

266.12

106

183.85

W

74

95.94

Mo

42

52.00

24

Cr

140.12

Pr

59

Ce

58

Db

262.11

260

Rf

105

180.95

Ta

73

92.91

Nb

41

50.94

V

23

Element

Atomic number

Bh

239.05

93

Np

144.91

61

Pm

264.12

107

186.21

Re

75

98.91

Tc

43

54.94

25

Mn

Relative atomic mass

104

178.49

Hf

72

91.22

Zr

40

47.90

22

Ti

5. The periodic table

Hs

239.05

94

Pu

150.35

62

Sm

269.13

108

190.23

Os

76

101.07

Ru

44

55.85

26

Fe

Mt

243.06

95

Am

151.96

63

Eu

268.13

109

192.22

Ir

77

102.91

Rh

45

58.93

27

Co

247.07

96

Cm

157.25

64

Gd

195.09

Pt

78

106.42

Pd

46

58.71

28

Ni

247.07

97

Bk

158.93

65

Tb

196.97

Au

79

107.87

Ag

47

63.55

29

Cu

252.08

98

Cf

162.50

66

Dy

200.59

Hg

80

112.41

Cd

48

65.38

30

Zn

254.09

99

Es

164.93

67

Ho

204.37

Tl

81

114.82

In

49

69.74

31

Ga

26.92

13

Al

10.81

5

B

3

253.09

100

Fm

167.26

68

Er

207.19

Pb

82

118.69

Sn

50

72.59

32

Ge

28.09

14

Si

12.01

6

C

4

257.10

101

Md

168.93

69

Tm

208.98

Bi

83

121.75

Sb

51

74.92

33

As

30.97

P

15

14.01

7

N

5

255.09

102

No

173.04

70

Yb

210

Po

84

127.60

Te

52

78.96

34

Se

32.06

S

16

16.00

8

O

6

Lr

257

103

174.97

71

Lu

209.99

At

85

126.90

I

53

79.91

35

Br

35.45

17

Cl

19.00

9

F

7

222.02

86

Rn

131.30

54

Xe

83.80

36

Kr

39.95

18

Ar

20.18

10

Ne

4.00

2

He

0

Chemistry data booklet

3

4

371

1795

1042

1323

1913

973

1413

300

950

Fr

Ra

Ac

3473

4875

5700

Ta

3269

Hf

2500

La

1194

942

Ba

5015

Nb

2740

3653

V

2163

4650

Zr

2125

3560

Ti

1933

3611

998

Cs

1657

302

959

3730

Sr

Rb

312

Y

3104

1757

Sc

1814

1033

Ca

1112

336

K

1380

Mg

1156

Na

922

3243

1615

Be

1551

Li

454

20

H

14

5933

W

3683

5833

Mo

2883

2943

Cr

2130

5900

Re

3453

5150

Tc

2445

2235

Mn

1517

5570

Os

2973

4173

Ru

2583

3023

Fe

1808

4403

Ir

2683

4000

Rh

2239

3143

Co

1768

Boiling point / K

Element

Melting point / K

4100

Pt

2045

3243

Pd

1827

3003

Ni

1728

3353

Au

1337

2485

Ag

1235

2840

Cu

1356

6. Melting points and boiling points of the elements

630

234

Hg

1038

594

Cd

1180

693

Zn

1730

Tl

577

2353

In

429

2676

303

Ga

2740

Al

933

2823

B

2573

2013

Pb

601

2543

Sn

505

3103

Ge

1210

2628

Si

1683

5100

C

3925

718

S

392

90

O

55

1833

Bi

544

2023

Sb

904

886

1235

Po

527

1263

Te

723

958

Se

1090

As

490

553

P

317

77

N

63

610

At

575

457

I

387

332

Br

266

238

Cl

172

85

F

53

Xe

211

202

Rn

166

161

121

116

Kr

87

84

Ar

27

25

Ne

4

1

He

Chemistry data booklet

Chemistry data booklet

Chemistry data booklet

550

0.8

–5

Ra

0.9

Fr

0.7

–10

0.9

509

0.8

–44

Ba

Cs

503

1.0

Rb

–46

Sr

47

1.0

0.8

393

376

Ca

K

–2

–14

1.3

–48 590

Mg

0.9

–53

1.6

738

Be

Li

900

1.0

–60

Na

403

419

496

520

–73

2.2

H

1312

Y

-30

1.1

1.1

Ac

499 –34

1.5

Ti

1.3

Hf

680

1.3

Zr

660

–18 658

–45

1.2

La

538

616

1.4

Sc

631

–41

–8

1.6

V

1.5

Ta

761

1.6
–31

–86

–51

Nb

664

650

1.7

W

770

2.2

Mo

1.7

Cr
685

653

–79

1.9

Re

760

2.1

Tc
–14

–53

1.6

Mn

717

–72 702

–64

Element

–101

2.2

Os

–106

2.2

Ru
840

711

1.8

Fe

759

–15

–64

880

2.2

Ir

–151

2.3

Rh

–110

1.9

Co
720

758

2.2

Pt

870 – 205 890

2.2

Pd

–54

1.9
731

–112 746

Ni
805

737

Electron affinity / kJ mol –1
2nd EA / kJ mol –1

Electronegativity

First ionization energy / kJ mol–1

1.7

Cd

1.7

Zn

2.4

Au

1.9

Hg

–223 1007

1.9

Ag

–126 868

1.9

Cu

–119 906

589

558

579

578

801

–41 762

–42 789

1.8

Tl

1.8

In

1.8

–19 716

–29 709

Ga

1.6

Al

2.0

B

3.0

N

1.8

Pb

2.0

Sn
–35 703

–107 834

2.0

Ge

–119 947

1.9

Si

1.9

Bi

2.1

Sb

F

–79 941

–91 812

Cl

2.6

3.0

Br

2.0

Po

–183

2.1

Te

2.2

At

–270

2.7

I

–190 1008 –295

2.6

Se

–195 1140 –325

3.2

S

–72 1000 –200 1251 –349
+640

4.0

O

3.4

1314 –141 1681 –328
+798

–101 869

2.2

As

2.2

P

–134 1012

2.6

C

–27 1086 –122 1402

7. First ionization energy, electron affinity and electronegativity of the elements

Rn

1037

Xe

1170

Kr

1351

Ar

1521

Ne

2081

He

2372

Chemistry data booklet

5

6

Ra

148 (2+)

Fr

180 (1+)

220

134 (2+)

167 (1+)

270

Ba

Cs

217

110 (2+)

148 (1+)

262

Sr

215

94 (2+)

Ca

Rb

244

133 (1+)

K

197

65 (2+)

98 (1+)

231

Mg

Na

160

30 (2+)

68 (1+)

186

Be

112

Li

152

154 (1–)

H

30

112 (3+)

Ac

188

115 (3+)

La

188

93 (3+)

Y

180

81 (3+)

Sc

160

76 (4+)

Hf

157

80 (4+)

Zr

157

Ti

90 (2+)
68 (4+)

146

64 (5+)
72 (6+)

Ta

143

72 (3+)
64 (5+)

Nb

141

88 (2+)

V

131

125

W

66 (4+)
42 (6+)

137

68 (4+)

Mo

136

63 (3+)

Cr

Ionic radius /
10–12 m

Re

63 (4+)
38 (7+)

137

Tc

65 (4+)
37 (7+)

135

Mn

80 (2+)
60 (4+)

129

Element

Os

63 (4+)
39 (8+)

134

68 (3+)
62 (4+)

Ru

133

Fe

76 (2+)
64 (3+)

126

Atomic radius /
10–12 m

Ir

68 (3+)
63 (4+)

135

Rh

67 (3+)
60 (4+)

134

Co

74 (2+)
63 (3+)

125

8. Atomic and ionic radii of the elements

80 (2+)
63 (4+)

Pt

138

Pd

86 (2+)
62 (4+)

138

72 (2+)

Ni

124

Au

137 (1+)
85 (3+)

144

126 (1+)

Ag

144

Cu

96 (1+)
69 (2+)

128

Hg

127 (1+)
110 (2+)

152

97 (2+)

Cd

149

74 (2+)

Zn

133

Tl

150 (1+)
93 (3+)

171

81 (3+)

In

166

62 (3+)

Ga

141

45 (3+)

Al

143

16 (3+)

B

88

Si

Pb

120 (2+)
84 (4+)

175

Sn

112 (2+)
71 (4+)

162

Ge

53 (4+)
272 (4–)

122

42 (4+)
271 (4–)

117

260 (4–)

C

77

Bi

120 (3+)
76 (5+)

170

245 (3–)

Sb

141

222 (3–)

As

121

212 (3–)

P

110

171 (3–)

N

70

Po

94 (4+)
67 (6+)

140

222 (2–)

Te

137

202 (2–)

Se

117

190 (2–)

S

104

146 (2–)

O

66

62 (7+)

At

140

219 (1–)

I

133

196 (1–)

Br

114

181 (1–)

Cl

99

133 (1–)

F

64

Rn

Xe

Kr

Ar

Ne

He

Chemistry data booklet

Chemistry data booklet

Chemistry data booklet

9. Covalent bond lengths
Bond

Bond

Bond length / nm

0.074
0.154
0.134
0.120
0.140
0.235
0.145
0.120
0.110
0.221
0.148
0.121
0.205
0.189
0.142
0.199
0.228
0.267

C–H
Si–H
N–H
P–H
O–H
S–H
F–H
Cl–H
Br–H
I–H

0.108
0.148
0.101
0.144
0.096
0.134
0.092
0.127
0.141
0.161

C–O
C=O
C–N
C=N
C≡N
C–F
C–Cl
C–Br
C–I

0.143
0.120
0.147
0.130
0.116
0.138
0.177
0.194
0.214

Si–O

H–H
C–C
C=C
C≡C
C C (in benzene)
Si–Si
N–N
N=N
N≡N
P–P
O–O
O=O
S–S
S=S
F–F
Cl–Cl
Br–Br
I–I

Bond length / nm

0.161

10. Bond enthalpies and average bond enthalpies at 298 K
Bond

ΔH / kJ mol –1

Bond

ΔH / kJ mol –1

Chemistry data booklet

436
347
612
838
505
226
158
410
945
198
144
498
266
158
243
193
151

C–H
Si–H
N–H
P–H
O–H
S–H
F–H
Cl–H
Br–H
I–H

413
318
391
321
464
364
568
432
366
298

C–O
C=O
C–N
C=N
C≡N
C–F
C–Cl
C–Br
C–I

358
746
286
615
887
467
346
290
228

Si–O

H–H
C–C
C=C
C≡C
C C (benzene)
Si–Si
N–N
N=N
N≡N
P–P
O–O
O=O
S–S
F–F
Cl–Cl
Br–Br
I–I

466
7

Chemistry data booklet

11. Organic compounds—thermodynamic data
Substance

Formula

methane ethane propane butane pentane hexane ethene propene but-1-ene cis-but-2-ene trans-but-2-ene ethyne propyne buta-1,3-diene cyclohexane benzene methylbenzene ethylbenzene phenylethene chloromethane dichloromethane trichloromethane bromomethane iodomethane chloroethane bromoethane chlorobenzene methanol ethanol phenol methanal ethanal propanone methanoic acid ethanoic acid benzoic acid methylamine CH4
C2H6
C3H8
C4H10
C5H12
C6H14
C2H4
C3H6
C4H8
C4H8
C4H8
C2H2
C3H4
C4H6
C6H12
C6H6
C6H5CH3
C6H5CH2CH3
C6H5CHCH2
CH3Cl
CH2Cl2
CHCl3
CH3Br
CH3I
C2H5Cl
C2H5Br
C6H5Cl
CH3OH
C2H5OH
C6H5OH
HCHO
CH3CHO
(CH3)2CO
HCOOH
CH3COOH
C6H5COOH
CH3NH2

State g g g g l l g g g g g g g g l l l l l g l l g l g l l l l s g g l l l s g ∆H Ö / f kJ mol–1
–75
–85
–105
–127
–173
–199
52
20
0*
–8
–12
228
187
110
–156
49
12
–13
104
–82
–124
–135
–37
–16
–137
–91
11
–239
–277
–165
–109
–191
–248
–425
–485
–385
–23

∆G Ö / f kJ mol–1
–51
–33
–23
–16
–9
–4
68
75
72
66
63
209
194
152
27
125
111
120
203
–57
–63
–71
–26
13
–53
94
–166
–175
–48
–113
–128
–155
–361
–390
–245
32

SÖ /

J K–1 mol–1
186
230
270
310
261
296
220
267
306
301
296
201
248
279
204
173
320
255
345
235
178
202
246
163

240
161
219
160
129
160
243

* (–0.4)

8

Chemistry data booklet

State g s s g g g g g l l l l g g g l l s g l l l l l l Formula

H2
S
C
CO
CH4
C2H6
C3H8
C4H10
C5H12
C6H14
C8H18
C6H12
C2H4
C4H6
C2H2
C6H6
C6H5CH3
C10H8
C2H5Cl
C2H5Br
C2H5I
C6H5CH2Cl
CHCl3
CH3OH
C2H5OH

hydrogen sulfur carbon (graphite) carbon monoxide methane ethane propane butane pentane hexane octane cyclohexane ethene buta-1,3-diene ethyne benzene methylbenzene naphthalene chloroethane bromoethane iodoethane (chloromethyl)benzene trichloromethane methanol ethanol (∆H  ) c Substance

The values of the molar enthalpy of combustion

12. Enthalpies of combustion

–286
–297
–394
–283
–890
–1560
–2219
–2877
–3509
–4163
–5470
–3920
–1411
–2541
–1301
–3267
–3910
–5156
–1413
–1425
–1467
–3709
–474
–726
–1367

∆H  / kJ mol–1 c propan-1-ol butan-1-ol cyclohexanol phenol ethoxyethane methanal ethanal benzaldehyde propanone pentan-3-one phenylethanone methanoic acid ethanoic acid benzoic acid ethanedioic acid ethyl ethanoate ethanamide methylamine ethylamine phenylamine nitrobenzene urea glucose sucrose

Substance
C3H7OH
C4H9OH
C6H11OH
C6H5OH
(C2H5)2O
HCHO
CH3CHO
C6H5CHO
(CH3)2CO
(C2H5)2CO
CH3COC6H5
HCOOH
CH3COOH
C6H5COOH
(COOH)2
CH3COOC2H5
CH3CONH2
CH3NH2
C2H5NH2
C6H5NH2
C6H5NO2
CO(NH2)2
C6H12O6
C12H22O11

Formula
1
1 s s l g g l l l l l l s s l s g g l l s s s

State

–2021
–2676
–3727
–3053
–2724
–571
–1167
–3525
–1817
–3100
–4149
–254
–874
–3227
–243
–2238
–1185
–1085
–1740
–3393
–3088
–632
–2803
–5640

∆H  / kJ mol–1 c in the following table refer to a temperature of 298 K and a pressure of 1.01 × 105 Pa (1 atm).

Chemistry data booklet

Chemistry data booklet

9

Chemistry data booklet

13. Lattice enthalpies at 298 K (experimental and theoretical values)
Ö

The lattice enthalpy values ( ∆H lattice ) given relate to the endothermic process for a solid crystal breaking into gaseous ions.
For example, for an alkali metal halide:
MX(s) → M+(g) + X– (g)

Experimental values
The data in these two tables are experimental values obtained by means of a suitable Born–Haber cycle. Alkali metal halides

F

Cl

Br

I

Li
Na
K
Rb
Cs

1049
930
829
795
759

864
790
720
695
670

820
754
691
668
647

764
705
650
632
613

Other substances CaF2
BeCl2
MgCl2
CaCl2
SrCl2
BaCl2
MgO
CaO
SrO
BaO

10

Ö
∆H lattice / kJ mol–1

Ö
∆H lattice / kJ mol–1

2651
3033
2540
2271
2170
2069
3791
3401
3223
3054

Other substances
CuCl2
AgF
AgCl
AgBr
AgI

Ö
∆H lattice / kJ mol–1

2824
974
918
905
892

Chemistry data booklet

Chemistry data booklet

Theoretical values
These two tables contain lattice enthalpies calculated from electrostatic principles on the basis of a purely ionic model for the crystal.
Ö
∆H lattice / kJ mol –1

Alkali metal halides Li
Na
K
Rb
Cs

F

Cl

Br

I

1030
910
808
774
744

834
769
701
680
657

788
732
671
651
632

730
682
632
617
600

Other substances CaF2
MgO
CaO
SrO
BaO

Chemistry data booklet

Ö
∆H lattice / kJ mol–1

2640
3795
3414
3217
3029

Other substances
AgF
AgCl
AgBr
AgI

Ö
∆H lattice / kJ mol–1

953
910
897
881

11

Chemistry data booklet

14. Standard electrode potentials
Oxidized species

Reduced species

EÖ / V

Li+(aq) + e –

Li(s)

–3.04

K+(aq) + e –

K(s)

–2.93

Ca2+(aq) + 2e –

Ca(s)

–2.87

Na+(aq) + e –

Na(s)

–2.71

Mg2+(aq) + 2e –

Mg(s)

–2.37

Al3+(aq) + 3e –

Al(s)

–1.66

Mn2+(aq) + 2e –

Mn(s)

–1.19

½H2(g) + OH– (aq)

–0.83

Zn2+(aq) + 2e –

Zn(s)

–0.76

Fe2+(aq) + 2e –

H2O(l) + e –

Fe(s)

–0.45



Ni(s)

–0.26

Sn2+(aq) + 2e –

Sn(s)

–0.14

Pb2+(aq) + 2e –

Pb(s)

–0.13

2+

Ni (aq) + 2e

H+(aq) + e –

½H2(g)

0.00

Cu2+(aq) + e –

Cu+(aq)

+0.15

H2SO3(aq) + H2O(l)

+0.17

Cu(s)

+0.34

2OH– (aq)

+0.40

Cu(s)

+0.52

SO42– (aq) + 4H+(aq) + 2e –
Cu2+(aq) + 2e –
½O2(g) + H2O(l) + 2e –
Cu+(aq) + e –
½I2(s) + e



I (aq)

+0.54

3+



2+

Fe (aq)

+0.77

+

Ag (aq) + e



Ag(s)

+0.80

½Br2(l) + e





Br (aq)

+1.07

H2O(l)

+1.23

2Cr3+(aq) + 7H2O(l)

+1.33

Cl– (aq)

+1.36

Mn2+(aq) + 4H2O(l)

+1.51

F– (aq)

+2.87

Fe (aq) + e

½O2(g) + 2H+(aq) + 2e –
Cr2O72– (aq) + 14H+(aq) + 6e –
½Cl2(g) + e –
MnO4 – (aq) + 8H+(aq) + 5e –
½F2(g) + e –

12



Chemistry data booklet

Chemistry data booklet

15. Strengths of organic acids and bases
The acid strengths in the following tables are given in terms of pKa values, where pKa = –log10 Ka.
The dissociation constant Ka values are for aqueous solutions at 298 K.
Base strengths are given in terms of pKb values.

Carboxylic acids
Name

Formula

pKa

methanoic ethanoic propanoic butanoic 2-methylpropanoic pentanoic 2,2-dimethylpropanoic benzoic phenylethanoic

HCOOH
CH3COOH
CH3CH2COOH
CH3(CH2)2COOH
(CH3)2CHCOOH
CH3(CH2)3COOH
(CH3)3CCOOH
C6H5COOH
C6H5CH2COOH

3.75
4.76
4.87
4.83
4.84
4.83
5.03
4.20
4.31

Halogenated carboxylic acids
Name

Formula

pKa

chloroethanoic dichloroethanoic trichloroethanoic fluoroethanoic bromoethanoic iodoethanoic CH2ClCOOH
CHCl2COOH
CCl3COOH
CH2FCOOH
CH2BrCOOH
CH2ICOOH

2.87
1.35
0.66
2.59
2.90
3.18

Name

Formula

pKa

phenol
2-nitrophenol
3-nitrophenol
4-nitrophenol
2,4-dinitrophenol
2,4,6-trinitrophenol

C6H5OH
O2NC6H4OH
O2NC6H4OH
O2NC6H4OH
(O2N)2C6H3OH
(O2N)3C6H2OH

9.99
7.23
8.36
7.15
4.07
0.42

Phenols

Chemistry data booklet

13

Chemistry data booklet

Alcohols
Name

Formula

pKa

methanol ethanol CH3OH
C2H5OH

15.5
15.5

Name

Formula

pKb

ammonia methylamine ethylamine dimethylamine trimethylamine diethylamine triethylamine phenylamine NH3
CH3NH2
CH3CH2NH2
(CH3)2NH
(CH3)3N
(C2H5)2NH
(C2H5)3N
C6H5NH2

4.75
3.34
3.35
3.27
4.20
3.16
3.25
9.13

Amines

16. Acid–base indicators
Indicator

pKa

pH range

Colour change
Acid

methyl orange bromophenol blue bromocresol green methyl red bromothymol blue phenol red phenolphthalein 14

3.46
4.10
4.90
5.00
7.30
8.00
9.50

3.2–4.4
3.0–4.6
3.8–5.4
4.8–6.0
6.0–7.6
6.6–8.0
8.2–10.0

Alkali

red yellow yellow red yellow yellow colourless

yellow blue blue yellow blue red pink

Chemistry data booklet

Chemistry data booklet

17. Infrared data
Characteristic ranges for infrared absorption due to stretching vibrations in organic molecules. Bond

Organic molecules

Wavenumber / cm–1

iodoalkanes

490–620

C–Br

bromoalkanes

500–600

C–Cl

chloroalkanes

600–800

C–F

fluoroalkanes

1000–1400

C–O

alcohols, esters, ethers

1050–1410

C=C

alkenes

1610–1680

C=O

aldehydes, ketones, carboxylic acids and esters

1700–1750

C≡C

alkynes

2100–2260

O–H

hydrogen bonding in carboxylic acids

2500–3300

C–H

alkanes, alkenes, arenes

2850–3100

O–H

hydrogen bonding in alcohols and phenols 3200–3600

N–H

primary amines

3300–3500

C–I

Chemistry data booklet

15

Chemistry data booklet

18. 1H NMR data
Typical proton chemical shift values (δ) relative to tetramethylsilane (TMS) = 0.
R represents an alkyl group, and Hal represents F, Cl, Br, or I.
These values may vary in different solvents and conditions.
Type of proton

Chemical shift / ppm

CH3

0.9–1.0

CH2 R

1.3–1.4

CHR2

1.4–1.6

O
C

RO

2.0–2.5

CH2

O
C

R

2.2–2.7

CH2
CH3

2.5–3.5

H

1.8–3.1

CH2 Hal

3.5–4.4

O

3.3–3.7

C

R

C

CH 2

O
R

C

3.8–4.1

CH2

O
O
C

R
R

O
HC

9.0–13.0

H

O

H

4.0–12.0

CH2

4.5–6.0

OH

H
O
R

16

C

H

4.0–12.0
6.9–9.0

9.4–10.0

Chemistry data booklet

Chemistry data booklet

19. 2-Amino acids
Common name

Symbol

alanine

Ala

H 2N

CH

COOH

6.0

CH 3
H 2N

arginine

pH of isoelectric point Structural formula

CH

COOH

CH2 CH 2 CH2 NH

Arg

C

NH 2

10.8

NH
H 2N

asparagine

CH

Asn

COOH

CH 2 C

NH 2

5.4

O

aspartic acid cysteine Cys

glutamic acid

H 2N

Asp

Glu

COOH

CH 2 COOH
H 2N

CH

COOH

CH2 SH
H2N

CH

COOH

CH 2 CH2 COOH
H 2N

glutamine

CH

Gln

CH

2.8
5.1
3.2

COOH

CH2 CH 2 C

NH2

5.7

O
H 2N

Gly

CH2 COOH

H2N

glycine

CH

6.0

COOH

CH 2

histidine

His

7.6

N
N
H

isoleucine

H 2N

CH

COOH

H3C

Ile

CH

CH 2 CH3

H 2N

leucine

H2N

Chemistry data booklet

Lys

COOH

CH 2

Leu
H3C

lysine

CH

CH

CH

6.0

6.0
CH 3

COOH

CH 2 CH2 CH 2 CH 2 NH2

9.7

17

Chemistry data booklet

Common name

Symbol

methionine

Met

phenylalanine

Structural formula

Phe

H 2N

CH

COOH

CH2 CH 2 S CH3
H 2N CH COOH
H 2N CH COOH
CH2 CH 2 S CH3
CH2

pH of isoelectric point 5.7

5.5

COOH

proline

Pro

serine

Ser

threonine

Thr

HN

H 2N

6.3
CH

COOH

CH 2 OH
H 2N

CH

COOH

H 3C

CH

OH

H 2N

CH

5.7

COOH

5.6

CH2

tryptophan

5.9

Trp
N
H
H 2N

CH

COOH

CH2

tyrosine

5.7

Tyr

OH

valine

18

Val

H 2N

CH

COOH

H 3C

CH

CH 3

6.0

Chemistry data booklet

Chemistry data booklet

20. Structural formulas of some medicines and drugs
C

CH3

OH

O

H 2C

OH

C

CH3

H

O
H 3C

C

O

N

H

O

C

H 3C

CH 3

aspirin

H 3C

H2
C

N

CH 2

H 3C

H2
C

N

COOH

H

paracetamol (acetaminophen)

OH

C

ibuprofen

OH
CH 2

H 3C

O

O

H2
C

N

CH 2

C

CH3

O
O

O

O
OH

O

morphine

CH2

CH 3

codeine

CH
CH3

H

CH

HO

C

CH3

diamorphine (heroin)

OH

NH 2

O

N

CH2

O
CH 3

H3C
O

HO

CH 3
N

N

N

N
CH3

amphetamine

epinephrine (adrenaline)
R

N
CH3

N

C

H
N

O
O

H 3C
S
N

Chemistry data booklet

O

penicillin
(general structure)

O

N

CH 3
CH 3

C
HO

nicotine

caffeine

Cl

N

diazepam (Valium®)

19

Chemistry data booklet

H

O

O

N
N

O 2N

N

N
H 2N

N
H

N

N
H

O
H 2C

nitrazepam (Mogadon®)

indole

CH 2

CH2

OH

acyclovir
O

H 3C
O

O

CH 3
H 3C

O
N

H 3C

CH 3

cocaine

N

CH 2

CH 2

N

NH

C
O

lysergic acid diethylamide (LSD)

F 3C
O

CH 2

CH2

NH2+ Cl

_

CH3

fluoxetine hydrochloride (Prozac®)
CH 3

O
OH

N

O
NH

H 3C

O
CH 3

CH2

CH2

CH2

CH 2

O
CH3

O

thalidomide

tetrahydrocannabinol (THC)
H
O
O

P

H 3C
_

O

CH 2

N
H

CH 3

N+ H
CH2

H 3CO

CH 2

CH2

NH 2

Cl
Cl

H 3CO
OCH 3

Pt

NH3
NH3

cisplatin

mescaline

psilocybin
20

Chemistry data booklet

Chemistry data booklet

21. Structural formulas of some biological molecules
CH2OH
CH 2OH
O
O
HO
H
H
H
H
H
OH
OH H
O
H
H
OH
H

OH

H

CH2OH
O H HO CH 2
H
O
H
OH H
H HO
O
HO
CH 2OH
H

H

OH

lactose

H

sucrose

CH 3

CH3
CH

OH

OH

CH

C

CH

O

CH3
CH

CH

C

CH

CH2

OH

OH

O

CH 3
CH 3

HO

HC

OH
CH 2

retinol (vitamin A)

HO

ascorbic acid (vitamin C)
H3C

CH 3
CH 2
H CH 2
CH2
CH
C

CH 3

H3C

CH 2
CH 3
H CH 2
CH2
CH
C

CH 3

CH3

CH3

CH3

HC

HO

CH
CH 2

cholesterol
HO

vitamin D
CH 3 OH

H 3C

CH 3 C

CH 3 OH

O
CH 3

CH 3
HO

O
O

estradiol

Chemistry data booklet

progesterone

testosterone

21

Chemistry data booklet

OH

I

H

CH

CH2

N

I

O

HO

HO

I

CH 3

HO

NH 2
C
OH
CH 2 H C

I

O

epinephrine (adrenaline)

thyroxine
O

NH2
N
HC

C
N

C
C

H

N
CH
N

H2N

H

adenine

N
C

C
N

NH2
C
C

N

N

CH
N

O

H

O

N
C

C
N

N

CH
CH

H

guanine

cytosine

O
H

C

C

O
H

CH
CH

O

H

N
C

C
N

CH 3

C
CH

H

uracil

thymine

22. Structural formulas of some food chemistry molecules Natural pigments
Anthocyanins
R

R
OH

O

O

R
O

O+

HO

glucose

OH

quinoidal base (blue)

22

OH
R
O

glucose

OH

flavylium cation (red)

Chemistry data booklet

Chemistry data booklet

Carotenes

H 3C

CH3
CH

CH3
C

CH

H3C

CH3

CH

CH

CH

C

CH

CH

CH

CH

C

CH

CH

CH

CH3

CH3

CH

C

CH 3

CH
H 3C

CH 3

α-carotene

H 3C

CH 3
CH

CH3
C

CH

H 3C

CH 3

CH

CH

CH

C

CH

CH

CH

CH

C

CH

CH

CH

CH 3

CH3

CH

C

CH3

CH
H3C

CH3

β-carotene
Porphyrins
OH

O
H 2C

CH 2

H 3C

H 2C

N

O
H 3C

C
H

CH 3
H 3C

H2C

CH

H
H2C
O

CH
N

H 3C

N

CH 3

Mg

HC

R=CH3 (Chlorophyll a)
R=CHO (Chlorophyll b)

CH 2

N

N

CH

N

R

N

CH3

N

CH 2

HC

CH 2

Fe

HC
H 2C

HO

CH3

H

CH 2 H C
O
O
O
C
O

CH 3

C20H39

heme B

chlorophyll

Preservatives
OH

OH

CH 3
C

CH3

CH3
C
O

CH3
CH3

CH 3

2-tert-butyl-4-hydroxyanisole
(2-BHA)

Chemistry data booklet

CH3

O

CH3

3-tert-butyl-4hydroxyanisole (3-BHA)

H 3C
H 3C

CH3

OH

C

CH3
CH 3
C
CH 3

CH 3

3,5-di-tert-butyl-4hydroxytoluene (BHT)

23

Chemistry data booklet

Fatty acids
Fatty acid

Formula

Octanoic acid

CH3(CH2)6COOH

Lauric acid

CH3(CH2)10COOH

Stearic acid

CH3(CH2)16COOH

Oleic acid

CH3(CH2)7CH═CH(CH2)7COOH

Linoleic acid

CH3(CH2)4(CH═CHCH2)2(CH2)6COOH

Linolenic acid

CH3CH2(CH═CHCH2)3(CH2)6COOH

23. References
The data in tables 4–16 can be found in the following three sources.
Lide, DR. 2008. CRC Handbook of Chemistry and Physics. Boca Raton, USA. CRC Press.
Copyright 2008 by CRC Handbook of Chemistry and Physics. David R Lide. Reproduced by permission from Taylor and Francis Group, LLC, a division of Informa plc.
NVON. 2007. Binas. English Edition. Groningen, The Netherlands. Wolters–Noordhoff.
Royal Society of Chemistry. 2002. Royal Society of Chemistry Electronic Data Book CD-Rom.
London, UK. Reproduced by permission of The Royal Society of Chemistry.
For tables 17 and 18, in addition to the sources above, the data were informed by the following.
Aylward, G and Findlay, T. 2002. SI Chemical Data. 5th Edition. Queensland, Australia. John
Wiley & Sons.
Clugston, M and Flemming, R. 2000. Advanced Chemistry. Oxford, UK. Oxford University
Press.
Morrison, RT and Boyd, RN. 1987. Organic Chemistry. 5th Edition. Boston, Massachusetts,
USA. Allyn and Bacon, Inc.

24

Chemistry data booklet

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...The chemistry of perming & rebonding Some of us have naturally curly hair but want it straightened; others have it naturally straight but want it curly. But whatever the style you like to wear, there's chemistry involved in it! The structure of hair Hair is made mostly of a protein called keratin, which is also present in nails. In hair, keratin molecules are arranged in straight bundles. These bundles are held together by disulphide bonds (-S-S-), which give strength to the hair. Disulphide bonds are made by the amino acid called cysteine. The cysteine of one keratin molecule forms a disulphide bond with the cysteine of the neighbouring keratin molecule. The more disulphide bonds there are in a strand of hair, the straighter it is. Ammonium thioglycolate: the perm salt Ammonium thioglycolate (HSCH2CO2NH4) is a compound that can break disulphide bonds. This is because it contains a thiol group (-SH). The thiol group replaces one of the sulphur atoms in the disulphide bond, like this: Keratin-S-S-keratin + 2HS-CH2CO2NH4 --> -HO2CH2CS-SCH2CO2H + 2NH3 + 2HS-keratin When the disulphide bond is broken, the keratin bundles come apart, and hair is weakened. Ammonium thioglycolate is therefore used widely in beauty parlours when customers want their hair re-styled. However, if you use too much of it, or if the reaction is left for too long, you could end up going bald. So do not, ever, try it at home! If you have watched the film Legally Blonde, you'll have seen Reese Witherspoon......

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