Chemistry data booklet First assessment 2016 Edited in 2014 (version 2)

Diploma Programme Chemistry data booklet

Published June 2014 Published on behalf of the International Baccalaureate Organization, a not-for-profit educational foundation of 15 Route des Morillons, 1218 Le Grand-Saconnex, Geneva, Switzerland by the International Baccalaureate Organization (UK) Ltd Peterson House, Malthouse Avenue, Cardiff Gate Cardiff, Wales CF23 8GL United Kingdom Website: www.ibo.org © International Baccalaureate Organization 2014 The International Baccalaureate Organization (known as the IB) offers four high-quality and challenging educational programmes for a worldwide community of schools, aiming to create a better, more peaceful world. This publication is one of a range of materials produced to support these programmes. The IB may use a variety of sources in its work and checks information to verify accuracy and authenticity, particularly when using community-based knowledge sources such as Wikipedia. The IB respects the principles of intellectual property and makes strenuous efforts to identify and obtain permission before publication from rights holders of all copyright material used. The IB is grateful for permissions received for material used in this publication and will be pleased to correct any errors or omissions at the earliest opportunity. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, without the prior written permission of the IB, or as expressly permitted by law or by the IB’s own rules and policy. See http://www.ibo.org/copyright. IB merchandise and publications can be purchased through the IB store at http://store.ibo.org. Email: [email protected]

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4073

Contents

1. Some relevant equations......................................................................................................................................................... 1 2. Physical constants and unit conversions ......................................................................................................................... 2 3. The electromagnetic spectrum............................................................................................................................................. 3 4. Fundamental particles ............................................................................................................................................................. 3

5. Names of the elements ............................................................................................................................................................. 4 6. The periodic table ...................................................................................................................................................................... 6 7. Melting points and boiling points of the elements (at 101.325 kPa) .................................................................. 7 8. First ionization energy, electron affinity and electronegativity of the elements ........................................... 8 9. Atomic and ionic radii of the elements ............................................................................................................................. 9

10. Covalent bond lengths ........................................................................................................................................................ 10 11. Bond enthalpies and average bond enthalpies at 298 K ..................................................................................... 11

12. Selected compounds—thermodynamic data ........................................................................................................... 12 13. Enthalpies of combustion ................................................................................................................................................. 13 14. Common oxidation numbers of the 3d ions .............................................................................................................. 14 15. Spectrochemical series ...................................................................................................................................................... 14

16. Ligands ...................................................................................................................................................................................... 15 17. Colour wheel ........................................................................................................................................................................... 15 18. Lattice enthalpies at 298 K (experimental values) ................................................................................................ 16 19. Enthalpies of aqueous solutions .................................................................................................................................... 17 20. Enthalpies of hydration ..................................................................................................................................................... 18 21. Strengths of organic acids and bases ........................................................................................................................... 19

22. Acid-base indicators ............................................................................................................................................................ 21 23. Values of ionization constant .......................................................................................................................................... 22 24. Standard electrode potentials at 298 K ...................................................................................................................... 23

25. Activity series ......................................................................................................................................................................... 24 26. Infrared data ........................................................................................................................................................................... 25

27. 1H NMR data .......................................................................................................................................................................... 26 28. Mass spectral fragments lost ........................................................................................................................................... 27 29. Triangular bonding diagram ........................................................................................................................................... 28 30. Resin identification codes ................................................................................................................................................. 29

Chemistry data booklet

31. Representations of some materials molecules ........................................................................................................ 29

32. Solubility product constants at 298 K ......................................................................................................................... 30

33. 2-amino acids ......................................................................................................................................................................... 31

34. Lipids, carbohydrates and nucleotide components............................................................................................... 33 35. Vitamins and pigments ...................................................................................................................................................... 35 36. Binding energy curve .......................................................................................................................................................... 37 37. Representations of some medicinal molecules ....................................................................................................... 38 38. References ............................................................................................................................................................................... 40 Notes

This booklet cannot be used for paper 1 of the examination (SLP1 and HLP1), but the periodic table given in section 6 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, HLP2, SLP3 and HLP3).

Chemistry data booklet

1. Some relevant equations Topic

Equation

1.3

𝑃𝑃𝑃𝑃 = 𝑛𝑛𝑛𝑛𝑛𝑛

5.1

𝑞𝑞 = 𝑚𝑚𝑚𝑚∆𝑇𝑇

2.2 and C.4

8.3 12.1 15.2 16.2

𝑐𝑐 = 𝑣𝑣𝑣𝑣

𝑝𝑝𝑝𝑝 = − log10 [H3 O+ ] or

𝑝𝑝𝑝𝑝 = −log10 [H + ] 𝐸𝐸 = ℎ𝑣𝑣

∆𝐺𝐺 ᴏ = ∆𝐻𝐻 ᴏ − 𝑇𝑇∆𝑆𝑆 ᴏ −𝐸𝐸𝑎𝑎

𝑘𝑘 = 𝐴𝐴𝑒𝑒 𝑅𝑅𝑅𝑅

16.2 16.2 17.1 19.1 A.5 A.8 B.7 B.7

Chemistry data booklet

ln 𝑘𝑘 = ln

−𝐸𝐸𝑎𝑎 + ln 𝐴𝐴 𝑅𝑅𝑅𝑅

𝑘𝑘1 𝐸𝐸𝑎𝑎 1 1 = � − � 𝑘𝑘2 𝑅𝑅 𝑇𝑇2 𝑇𝑇1

∆𝐺𝐺 ᴏ = −𝑅𝑅𝑅𝑅 ln 𝐾𝐾

% atom economy =

∆𝐺𝐺 ᴏ = −𝑛𝑛𝑛𝑛𝑛𝑛 ᴏ

molar mass of desired product × 100 molar mass of all reactants 𝑛𝑛𝑛𝑛 = 2𝑑𝑑sin𝜃𝜃

𝑝𝑝𝑝𝑝 = 𝑝𝑝𝐾𝐾𝑎𝑎 + log � log10

[𝐴𝐴− ] � [𝐻𝐻𝐻𝐻]

𝐼𝐼0 = 𝜀𝜀𝜀𝜀𝜀𝜀 𝐼𝐼

1

Topic

Equation

C.1

Energy density =

C.1

Speci�ic energy =

C.3

energy released from fuel mass of fuel consumed

𝑁𝑁 = 𝑁𝑁0 𝑒𝑒 −𝜆𝜆𝜆𝜆

C.3 and D.8 C.6

energy released from fuel volume of fuel consumed

𝑡𝑡1 = 2

ln 2 𝜆𝜆

𝐸𝐸 = 𝐸𝐸 0 − �

C.7 D.8

𝑅𝑅𝑅𝑅 � ln 𝑄𝑄 𝑛𝑛𝑛𝑛

Rate1 𝑀𝑀2 =� Rate2 𝑀𝑀1 𝑡𝑡

𝑁𝑁𝑡𝑡 = 𝑁𝑁0 (0.5) �𝑘𝑘

2. Physical constants and unit conversions Avogadro’s constant (𝐿𝐿 or 𝑁𝑁𝐴𝐴 ) = 6.02 × 1023 mol−1

Gas constant (𝑅𝑅) = 8.31 J K −1 mol−1

Molar volume of an ideal gas at STP = 2.27 × 10−2 m3 mol−1 = 22.7 dm3 mol−1

1 dm3 = 1 litre = 1 × 10−3 m3 = 1 × 103 cm3 STP conditions = 273 K and 100 kPa

SATP conditions = 298 K and 100 kPa Speed of light = 3.00 × 108 ms −1

Specific heat capacity of water = 4.18 kJ kg −1 K −1 = 4.18 J g −1 K −1

Planck’s constant (ℎ) = 6.63 × 10−34 J s

Faraday’s constant (𝐹𝐹) = 9.65 × 104 C mol−1

Ionic product constant for water (𝐾𝐾w ) = 1.00 × 10−14 mol2 dm−6 at 298 K

1 amu = 1.66 × 10−27 kg

2

Chemistry data booklet

3. The electromagnetic spectrum energy

−16 −14 −10 −8 −12 10 10−14 10 10−12 10 10−10 10 10−8 10−16 10

γ rays

X-rays

UV

−6 10 10−6

IR

−4 10 10−4

−2 10 10−2

2 10 102

0 10 100

microwaves

4 10 104

6 10 106

radio waves

108

wavelength / nm 108

V I B G Y O R

700

400

wavelength / nm

4. Fundamental particles Mass (kg)

Charge (C)

Chemistry data booklet

Proton

Neutron

Electron

1.602189 × 10−19

0

−1.602189 × 10−19

1.672622 × 10−27

1.674927 × 10−27

9.109383 × 10−31

3

4

5. Names of the elements Element

Chemistry data booklet

actinium aluminium americium antimony argon arsenic astatine barium berkelium beryllium bismuth bohrium boron bromine cadmium caesium calcium californium carbon cerium chlorine chromium cobalt copernicium copper curium darmstadtium dubnium

Symbol Ac Al Am Sb Ar As At Ba Bk Be Bi Bh B Br Cd Cs Ca Cf C Ce Cl Cr Co Cn Cu Cm Ds Db

Atomic number 89 13 95 51 18 33 85 56 97 4 83 107 5 35 48 55 20 98 6 58 17 24 27 112 29 96 110 105

Element

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

Symbol 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

Atomic number 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

Chemistry data booklet

Element

meitnerium 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 roentgenium rubidium

Symbol Mt 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 Rg Rb

Atomic number 109 101 80 42 60 10 93 28 41 7 102 76 8 46 15 78 94 84 19 59 61 91 88 86 75 45 111 37

Element

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 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

Atomic number 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

5

6

6. The periodic table 1 2 3 4 5 6 7

1

2

1.01 3

4

1

H

Li

6.94 11

Na

Mg

Rb

Sr

85.47 55

Cs

132.91 87

Fr

(223)

5

6

7

Ca

40.08 38 87.62 56

Ba

137.33 88

Ra

(226)

8

Atomic number

9

10

11

12

Element

Be

24.31 20

39.10 37

4

21

Sc

44.96 39

Y

88.91 57 †

La

22

Ti

47.87 40

Zr

91.22 72

Hf

Chemistry data booklet

138.91 89 ‡

178.49 104

†

Ce

Ac

(227)

‡

Rf

(267) 58

140.12 90

Th

232.04

23

V

50.94 41

Nb

92.91 73

Ta

180.95 105

Db

(268) 59

Pr

140.91 91

Pa

231.04

24

Cr

52.00 42

Mo

95.96 74

W

183.84 106

Sg

(269) 60

Nd

144.24 92

U

238.03

25

Mn

54.94 43

Tc

(98) 75

Re

186.21 107

Bh

(270) 61

Pm

(145) 93

Np

(237)

26

Fe

27

Co

58.93

101.07 76

102.91 77

Os

190.23 108

Hs

(269) 62

Sm

150.36 94

Pu

(244)

14

15

16

17

5

6

7

8

9

10.81 13

55.85

44 Ru

13

B

Relative atomic mass

9.01 12

22.99 19

K

3

45 Rh Ir

192.22 109

Mt

(278) 63

Eu

151.96 95

Am

(243)

28

Ni

58.69 46

Pd

106.42 78

Pt

195.08 110

Ds

(281) 64

Gd

157.25 96

Cm

(247)

29

Cu

63.55 47

Ag

107.87 79

Au

196.97 111

Rg

(281) 65

Tb

158.93 97

Bk

(247)

30

Zn

65.38 48

Cd

112.41 80

Hg

200.59 112

Cn

(285) 66

Dy

162.50 98

Cf

(251)

Al

26.98 31

Ga

69.72 49

In

114.82 81

Tl

204.38 113

Uut

(286) 67

Ho

164.93 99

Es

(252)

C

N

12.01

14.01

28.09 32

30.97 33

14 Si Ge

72.63 50

Sn

118.71 82

Pb

207.20 114

Uuq

(289) 68

Er

167.26 100

Fm

(257)

15 P As

74.92 51

Sb

121.76 83

Bi

208.98 115

Uup

(288) 69

Tm

168.93 101

Md

(258)

O

16.00 16

S

32.07 34

Se

78.96 52

Te

127.60 84

Po

(209) 116

Uuh

(293) 70

Yb

173.05 102

No

(259)

F

19.00 17

Cl

35.45 35

Br

79.90 53

I

126.90 85

At

(210) 117

Uus

(294) 71

Lu

174.97 103

Lr

(262)

18 2

He

4.00 10

Ne

20.18 18

Ar

39.95 36

Kr

83.90 54

Xe

131.29 86

Rn

(222) 118

Uuo

(294)

Chemistry data booklet

7. Melting points and boiling points of the elements (at 101.325 kPa) −259.2

H

−252.9 180.5

Li

Melting point (°C) 1287

Be

1342 97.79

2468 650.0

K

Ca

Na

882.9 63.38

Element

Mg

2077

B

Boiling point (°C)

4000 660.3

1090 842.0

1541

1670

1910

1907

1246

1538

1495

1455

1085

39.30

768.8

1522

1854

2477

2622

2157

2333

1963

1555

961.8

28.44

725.0

1768

1064

758.8

Rb

687.8

Cs

670.8 27.00

Fr

676.8

1484

Sr

1377

Ba

1845 699.8

Ra

1140

Sc

2836

Y

3345

920.0

La

3464 1050

Ac

3200

Ti

3287

Zr

4406 2233

Hf

4600

V

3407

Nb

4741 3017

Ta

5455

Cr

2671

Mo

4639 3414

W

5555

Mn

2061

Tc

4262 3453

Re

5900

Fe

2861

Ru

4147 3033

Os

5008

Co

2927

Rh

3695 2446

Ir

4428

Ni

2913

Pd

2963

Pt

3825

Cu

2560

Ag

2162

Au

2836

Al

3500

C

4827 1414

Si

419.5

2519 29.77

3265 938.2

321.1

156.6

231.9

−38.83

303.8

327.5

Zn

907.0

Cd

766.8

Hg

356.6

Ga

2229

In

2027

Tl

1473

Ge

2833

Sn

2586

Pb

1749

−210.0

N

−195.8 44.15

P

280.5 816.8

As

613.0

630.6

Sb

1587

271.4

Bi

1564

−218.8

O

−183.0 115.2

S

444.6 220.8

Se

684.8

449.5

Te

987.8

253.8

Po

962.0

−219.7

F

−188.1 −101.5

Cl

−34.04 −7.050

Br

58.78

113.7

I

184.4 301.8

At

336.8

He

−268.9 −248.6

Ne

−246.0 −189.3

Ar

−185.8 −157.4

Kr

−153.4 −111.8

Xe

−108.1 −71.15

Rn

−61.85

7

8

8. First ionization energy, electron affinity and electronegativity of the elements 131

H

−73

2.2

520

−60

Li

1.0

496

−53

Na 0.9

419

K

−48

0.8

403

−47

Rb 0.8

376

−46

Cs

0.8

393

−47

Fr

0.7

900

738

First ionization energy (kJ mol−1)

Be

1.3

590

Ca

1.0

549

Sr

−2

−5

1.0

503

−14

Ba

0.9

509

−10

Ra

0.9

801

Element

Electronegativity

1.6

Mg

Electron affinity (kJ mol−1) (2nd EA / kJ mol−1)

633

−18

Sc

1.4

600

Y

−30

1.2

538

−45

La

1.1

499

−34

Ac

1.1

659

Ti

−8

1.5

640

−41

Zr

1.3

659

Hf

1.3

−1

651

V

−51

1.6

652

−88

Nb 1.6

728

−31

Ta

1.5

653

−64

Cr

1.7

684

−72

Mo 2.2

759

−79

W

1.7

717

Mn 1.6

702

−53

Tc

2.1

756

−14

Re 1.9

B

−27

2.0

578

762

−15

Fe

1.8

710

−101

Ru 2.2

814

−106

Os

2.2

760

−64

Co

1.9

720

−110

Rh 2.3

865

−151

Ir

2.2

737

−112

Ni

1.9

804

−54

Pd 2.2

864

−205

Pt

2.2

745

−119

Cu 1.9

731

−126

Ag 1.9

890

−223

Au 2.4

906

868

Zn

1.6

Cd 1.7

1007

Hg 1.9

−42

Al

1.6

579

−41

Ga

1.8

558

−29

In

1.8

589

−36

Tl

1.8

1086 −122

C

2.6

787

−134

Si

1.9

762

−119

Ge

2.0

709

−107

Sn

2.0

716

−35

Pb 1.8

1402

N

3.0

1012

P

−72

2.2

944

−78

As

2.2

831

−101

Sb

2.0

703

−91

Bi

1.9

2372

He

1314 −141 (+753)

1681 −328

2081

3.4

1000 −200 (+545)

4.0

1251 −349

1520

2.6

3.2

1140 −325

1351

2.6

3.0

1008 −295

1170

2.1

2.7

2.0

2.2

O

941

869

S

−195

Se

−190

Te

812

−183

Po

F

Cl

Br I

−270

At

Ne Ar

Kr

Xe

2.6

1037

Rn

Chemistry data booklet

Chemistry data booklet

9. Atomic and ionic radii of the elements 32

H

130

Li

Atomic radius (10−12 m)

Na

Mg

140

102 (1+)

72 (2+)

K

138 (1+)

Ca

100 (2+)

75 (3+)

Rb

152 (1+)

Sr

118 (2+)

Y

90 (3+)

Cs

167 (1+)

Ba

135 (2+)

La

103 (3+)

Fr

Ra

Ac

200 215 238 242

174 190 206 211

84

Ionic radius (10−12 m)

Be

45 (2+)

160

Element

99

76 (1+)

37

159

Sc

148

Ti

176

86 (2+) 61 (4+) 164

194

164

201

Zr

72 (4+)

Hf

71 (4+)

144

V

79 (2+) 54 (5+) 156

Nb

72 (3+) 64 (5+) 158

Ta

64 (5+)

130

Cr

129

Mn

62 (3+) 44 (6+) 146

83 (2+) 53 (4+) 138

150

141

Mo

65 (4+)

W

66 (4+) 60(6+)

Tc

65(4+)

Re

63(4+) 53(7+)

124

Fe

B

Co

117

Ni

122

Cu

120

Zn

16 (4+)

146 (3−)

140 (2−)

133 (1−)

Al

Si

P

S

Cl

196 (1−)

Sb

76 (3+) 150

Te

221 (2−)

220(1−)

Bi

142

I

Po

At

Ir

Pt

Au

Hg

Tl

80(2+) 63(4+)

62(3+)

130

Cd

132

In

137 (1+)

85 (3+)

119 (1+) 102 (2+)

146

198 (2−)

Br

Os

68(+3) 63 (+4)

148

58 (3+) 46 (5+) 140

Se

80(3+)

63 (4+) 55(6+)

136

As

95 (2+)

86(2+) 62(4+) 130

136

Ge

115 (1+)

67 (+3) 60 (+4) 132

116

Ga

Pd

68(3+) 62 (4+) 136

117

181 (1−)

74 (2+) 140

101

184 (2−)

123 142

120

53 (4+) 272(4−) 140

Sn

144

118(2+) 69 (4+) 145

89 (3)

78 (4+)

150 (1+)

Pb

119 (2+)

120

103 (3+)

76(5+)

118 137

97(4+)

62

Ne

100

38 (5+)

77 (1+) 73 (2+) 136

Ag

104

40 (4+)

69 (2+) 130

109

F

54 (3+)

65(+2) 55 (+3) 134

Rh

60

27 (3+)

114

O

64

N

61 (2+) 55 (3+) 136

Ru

71

C

124

118

75

He

Ar

Kr

Xe

Rn

9

10. Covalent bond lengths Single bonds (𝟏𝟏𝟏𝟏−𝟏𝟏𝟏𝟏 𝐦𝐦 = 𝐩𝐩𝐩𝐩) Br

C

Cl

H

I

N

O

147

143

136

142

Br

228

194

214

176

141

247

214

Cl

214

177

199

163

128

232

197

C F

H I

N O

194 176 141 247 214

P

220

Si

216

S

227

154 138 108 214 147 143 184 182 185

177 163 128

138 142 92

108 92 74

232

257

160

170

142

97

197 203 199 202

Multiple bonds (𝟏𝟏𝟏𝟏−𝟏𝟏𝟏𝟏 𝐦𝐦 = 𝐩𝐩𝐩𝐩)

136

101

214 257 160 267

154

142

247

156

148

243

158

134

101 146 136 175 174

170 97

136

P

227

216

203

199

202

184 154 142 247 154

161

210

163

221

182 158 134 175 161 210 205 215

C≡N 116

N≡N 110

C C 140 (in benzene)

C=S 156

O=O 121

C=N 130

C=O 122

N=N 125

Si

220

148 154

S

C=C 134 C≡C 120

10

F

185 156 148 243 174 163 215 232

N=O 114

S=S 189

Chemistry data booklet

11. Bond enthalpies and average bond enthalpies at 298 K Single bonds (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 ) Br

C

Cl

F

H

I

N

228

286

280

278

Br

193

285

219

249

366

178

Cl

219

324

242

255

431

211

C F

H I

N

285 249 366 178

O

201

S

218

P

Si

264 330

346 492 414 228 286 358 264 289 307

324 255 431 211 192 206 322 271 400

Multiple bonds (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

492 159 567 280 278 191 490 327 597

414 567 436 298 391 463 322 364 323

298 151 201 184 234

192 391 158 214

O

P

S

201

264

218

330

206

322

271

400

358 191 463 201 214 144 363 466

264 490 322 184

289 327 364

363 198

266 293

C≡N 890

N≡N 945

C C 507 (in benzene)

C=S 536

O=O 498

C=N 615

Chemistry data booklet

C=O 804

N=N 470

307 597 323 234 466

C=C 614 C≡C 839

Si

293 226

N=O 587

S=S 429

11

12. Selected compounds—thermodynamic data Substance

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 water steam carbon monoxide carbon dioxide hydrogen bromide hydrogen chloride hydrogen fluoride hydrogen iodide

12

Formula

CH4 C2 H6 C3 H8 C4 H10 C5 H12 C6 H14 C2 H4 C3 H6 C4 H8 C4 H8 C4 H8 C2 H2 C3 H4 C4 H6 C6 H12 C6 H6 C6 H5 CH3 C6 H5 CH2 CH3 C6 H5 CHCH2 CH3 Cl CH2 Cl2 CHCl3 CH3 Br CH3 I C2 H5 Cl C2 H5 Br C6 H5 Cl CH3 OH C2 H5 OH C6 H5 OH HCHO CH3 CHO (CH3 )2 CO HCOOH CH3 COOH C6 H5 COOH CH3 NH2 H2 O H2 O CO CO2 HBr HCl HF HI

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 l g g g g g g g

∆𝑯𝑯ᴏ𝐟𝐟 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 ) −74.0 −84.0 −105 −126 −173 −199 +52.0 +20.0 +0.10 −7.0 −11.0 +228 +185 +110 −156 +49.0 +12.0 −12.0 +104 −82.0 −124 −134 −36.0 −14.0 −137 −90.0 +11.0 −239 −278 −165 −109 −166 −248 −425 −484 −385 −23 −285.8 −241.8 −110.5 −393.5 −36.3 −92.3 −273.3 +26.5

∆𝑮𝑮ᴏ𝐟𝐟 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

𝑺𝑺ᴏ (𝐉𝐉 𝐊𝐊 −𝟏𝟏 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

+68.0 +62.0 +71.0 +66.0 +63.0 +211 +194 +151

+220 +267 +306 +301 +297 +201 +248 +279

−58.0

+235 +178 +202 +246 +163

−50.0 −32.0 −24.0 −17.0

+125

−74.0 −26.0 −53.0 −26.0 −167 −175 −102 −133 −361 −390

+32.0 −237.1 −228.6 −137.2 −394.4 −53.4 −95.3 −275.4 +1.7

+186 +230 +270 +310

+173

+199

+127 +161 +144 +219 +264 +200 +129 +160 +168 +243 +70.0 +188.8 +197.7 +213.8 +198.7 +186.9 +173.8 +206.6

Chemistry data booklet

Chemistry data booklet

13. Enthalpies of combustion

The values of the molar enthalpy of combustion(∆𝐻𝐻𝑐𝑐ᴏ ) in the following table refer to a temperature of 298 K and a pressure of 1.00 × 105 Pa . Substance

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

Formula

H2 S C CO CH4 C2 H6 C3 H8 C4 H10 C5 H12 C6 H14 C8 H18 C6 H12 C2 H4 C4 H6 C2 H2 C6 H6 C6 H5 CH3 C10 H8 C2 H5 Cl C2 H5 I CHCl3 CH3 OH C2 H5 OH

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

∆𝑯𝑯ᴏ𝐜𝐜 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 ) −286 −297 −394 −283 −891 −1561 −2219 −2878 −3509 −4163 −5470 −3920 −1411 −2541 −1301 −3268 −3910 −5156 −1413 −1463 −473 −726 −1367

Substance

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 phenylamine nitrobenzene urea glucose sucrose

Formula

C3 H7 OH C4 H9 OH C6 H11 OH C6 H5 OH (C2 H5 )2 O HCHO CH3 CHO C6 H5 CHO (CH3 )2 CO (C2 H5 )2 CO CH3 COC6 H5 HCOOH CH3 COOH C6 H5 COOH (COOH)2 CH3 COOC2 H5 CH3 CONH2 CH3 NH2 C6 H5 NH2 C6 H5 NO2 CO(NH2 )2 C6 H12 O6 C12 H22 O11

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

∆𝑯𝑯ᴏ𝐜𝐜 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 ) −2021 −2676 −3728 −3053 −2724 −571 −1167 −3525 −1790 −3100 −4149 −255 −874 −3228 −243 −2238 −1186 −1086 −3393 −3088 −633 −2803 −5640

13

14. Common oxidation numbers of the 3d ions Sc

+3

Ti

V

Cr

Mn

Fe

Co

Ni

+2

+2

+2

+2

+2

+2

+2

+4

+4

+3

+3 +5

+3

+6

+3 +4

+3

+3

Cu

Zn

+2

+2

+1

+6 +7

15. Spectrochemical series

Ligands can be arranged in a spectrochemical series according to the energy difference they produce between the two sets of d-orbitals in an octahedral complex. I − < Br − < S2− < Cl− < F − < OH− < H2 O < SCN− < NH3 < CN− ≈ CO

14

Chemistry data booklet

16. Ligands

NH2

NH2

1,2-ethanediamine

HO N

O

O O

O HO N

O–

O

O HO

O–

ethanedioate

OH

EDTA

17. Colour wheel 647 nm

700 nm 400 nm

585 nm

Red

Yellow

Violet

Green

424 nm

Chemistry data booklet

Orange

Blue

575 nm

491 nm

15

18. Lattice enthalpies at 298 K (experimental values)

ᴏ The lattice enthalpy values (∆𝐻𝐻lattice ) given relate to the endothermic process Ma Xb (s) → aMb+ (g) + bX a− (g) in which the gaseous ions of a crystal are separated to an infinite distance from each other.

Experimental values

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

Cl

Br

I

Li

1049

864

820

764

K

829

720

691

650

Na Rb Cs

930

790

795

754

695

759

668

670

647

705 632 613

Other substances

∆𝑯𝑯ᴏ𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

Other substances

∆𝑯𝑯ᴏ𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

BeCl2

3033

BaO

3054

CaF2

MgCl2 CaCl2 SrCl2

BaCl2 MgO CaO

16

F

∆𝑯𝑯ᴏ𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥𝐥 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

2651

SrO

2540

CuCl2

2170

AgCl

2271 2069 3791 3401

AgF

AgBr AgI

3223 2824 974 918 905 892

Chemistry data booklet

19. Enthalpies of aqueous solutions Solute

∆𝑯𝑯ᴏ𝐬𝐬𝐬𝐬𝐬𝐬 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

Solute

∆𝑯𝑯ᴏ𝐬𝐬𝐬𝐬𝐬𝐬 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

NH4 NO3

+25.69

KBr

+19.87

LiCl

−37.03

RbF

LiI

−63.30

RbBr

+3.88

CsF

NH4 Cl LiF

LiBr NaF

NaCl

NaBr NaI KF

Chemistry data booklet

+14.78 +4.73

−48.83 +0.91 −0.60 −7.53

−17.73

KCl KI

RbCl RbI

CsCl

CsBr CsI

+17.22 +20.33 −26.11 +17.28 +21.88 +25.10 −36.86 +17.78 +25.98 +33.35

17

20. Enthalpies of hydration Cations

∆𝑯𝑯ᴏ𝐡𝐡𝐡𝐡𝐡𝐡 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

Anions

∆𝑯𝑯ᴏ𝐡𝐡𝐡𝐡𝐡𝐡 (𝐤𝐤𝐤𝐤 𝐦𝐦𝐦𝐦𝐦𝐦−𝟏𝟏 )

Na+

−424

Cl−

−359

Li+ K+

Rb+ Cs +

F−

−340

Br −

−291

ClO− 3

−315

I−

Be2+

−2524

BrO− 3

Ca2+

−1616

ClO− 4

−1346

CN−

Mg 2+ Sr 2+

Ba2+

Ra2+ Al3+

Ga3+ In3+ Tl3+ Tl+

Sn2+

Pb2+

18

−538

−1963 −1483 −1335

IO− 3

OH− NO− 3

−4741

HCO− 3

−4171

HSO− 4

−346

PO3− 4

−4745 −4163 −1587

−504 −328 −287 −331 −358 −446 −205 −519 −341 −316 −383

CO2− 3

−1486

SO2− 4

−1099

−362

−2921

−1523

Chemistry data booklet

21. Strengths of organic acids and bases

The acid strengths in the following tables are given in terms of p𝐾𝐾a values, where p𝐾𝐾a = −log10 𝐾𝐾a .

The dissociation constant 𝐾𝐾a values are for aqueous solutions at 298 K . Base strengths are given in terms of p𝐾𝐾b values.

Carboxylic acids Name

Formula

ethanoic

CH3 COOH

methanoic propanoic butanoic

HCOOH

3.75

CH3 CH2 COOH

4.87

CH3 (CH2 )2 COOH

2-methylpropanoic

(CH3 )2 CHCOOH

2,2-dimethylpropanoic

(CH3 )3 CCOOH

phenylethanoic

C6 H5 CH2 COOH

Name

Formula

dichloroethanoic

CHCl2 COOH

pentanoic benzoic

Halogenated carboxylic acids chloroethanoic

trichloroethanoic

CH3 (CH2 )3 COOH C6 H5 COOH

4.83 4.84 4.83 5.03 4.20 4.31

𝐩𝐩𝑲𝑲𝐚𝐚

2.87

CCl3 COOH

0.66

CH2 FCOOH

iodoethanoic

CH2 ICOOH

Chemistry data booklet

4.76

CH2 ClCOOH

fluoroethanoic

bromoethanoic

𝐩𝐩𝑲𝑲𝐚𝐚

CH2 BrCOOH

1.35 2.59 2.90 3.18

19

Phenols Name

Formula

2-nitrophenol

O2 NC6 H4 OH

phenol

3-nitrophenol 4-nitrophenol

2,4-dinitrophenol

C6 H5 OH

9.99

O2 NC6 H4 OH

8.36

O2 NC6 H4 OH

(O2 N)2 C6 H3 OH

2,4,6-trinitrophenol

(O2 N)3 C6 H2 OH

Name

Formula

ethanol

C2 H5 OH

Alcohols methanol

𝐩𝐩𝑲𝑲𝐚𝐚

7.23 7.15 4.07 0.42

𝐩𝐩𝑲𝑲𝐚𝐚

CH3 OH

15.5

Name

Formula

𝐩𝐩𝑲𝑲𝐛𝐛

methylamine

CH3 NH2

Amines ammonia

ethylamine

dimethylamine

NH3

4.75

CH3 CH2 NH2

3.35

(CH3 )2 NH

trimethylamine

(CH3 )3 N

triethylamine

(C2 H5 )3 N

diethylamine phenylamine

20

15.5

(C2 H5 )2 NH C6 H5 NH2

3.34 3.27 4.20 3.16 3.25 9.13

Chemistry data booklet

22. Acid-base indicators

Colour change

Indicator

𝐩𝐩𝑲𝑲𝐚𝐚

pH range

Acid

bromophenol blue

4.2

3.0–4.6

yellow

4.4–6.2

red

yellow

yellow

red

methyl orange

bromocresol green methyl red

bromothymol blue phenol red

phenolphthalein

Chemistry data booklet

3.7 4.7 5.1 7.0 7.9 9.6

3.1–4.4

3.8–5.4

red

yellow

yellow

blue

6.0–7.6

yellow

8.3–10.0

colourless

6.8–8.4

Alkali blue

blue

pink

21

23. Values of the ionization constant of water Temperature (°𝐂𝐂) 0

0.113 × 10−14

10

0.292 × 10−14

20

0.684 × 10−14

5

15 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95

100

22

𝑲𝑲𝐰𝐰 value

0.185 × 10−14

0.453 × 10−14 1.00 × 10−14 1.47 × 10−14 2.09 × 10−14 2.92 × 10−14 4.02 × 10−14 5.43 × 10−14 7.24 × 10−14 9.55 × 10−14 12.4 × 10−14 15.9 × 10−14 20.1 × 10−14 25.2 × 10−14 31.3 × 10−14 38.3 × 10−14 46.6 × 10−14

56.0 × 10−14

Chemistry data booklet

Chemistry data booklet

24. Standard electrode potentials at 298 K Oxidized species Li+ (aq) + e− K + (aq) + e−

Ca2+ (aq) + 2e− Na+ (aq) + e−

Mg 2+ (aq) + 2e− Al3+ (aq) + 3e−

Mn2+ (aq) + 2e− H2 O(l) + e−

Zn2+ (aq) + 2e− Fe2+ (aq) + 2e− Ni2+ (aq) + 2e−

Sn2+ (aq) + 2e−

Pb2+ (aq) + 2e− H + (aq) + e−

Reduced species

𝑬𝑬ᴏ (𝐕𝐕)

Oxidized species

K(s)

−2.93

+ − SO2− 4 (aq) + 4H (aq) + 2e

Li(s)

Ca(s)

−2.87

Na(s)

−2.71

Mg(s)

−2.37

Al(s)

Mn(s)

1 H (g) 2 2

Zn(s) Fe(s) Ni(s)

Sn(s)

Pb(s)

1 H (g) 2 2

−3.04

Cu2+ (aq) + e−

1 O (g) 2 2

+ e−

Ag + (aq) + e−

−0.83 −0.45

Cu+ (aq) + e−

Fe3+ (aq) + e−

−1.18 −0.76

+ H2 O(l) + 2e− 1 I (s) 2 2

−1.66 + OH − (aq)

Cu2+ (aq) + 2e−

1 O (g) 2 2

1 Br (l) 2 2

+ e−

+ 2H2 (aq) + 2e−

−0.26

+ − Cr2 O2− 7 (aq) + 14H (aq) + 6e

−0.13

+ − MnO− 4 (aq) + 8H (aq) + 5e

−0.14 0.00

1 Cl (g) 2 2

+ e−

1 F (g) 2 2

+ e−

Reduced species

𝑬𝑬ᴏ (𝐕𝐕)

H2 SO3 (aq) + H2 O(l)

+0.17

Cu+ (aq) Cu(s)

2OH − (aq) Cu(s)

I − (aq)

Fe2+ (aq) Ag(s)

Br − (aq) H2 O(l)

2Cr 3+ (aq) + 7H2 O(l) Cl− (aq)

Mn2+ + 4H2 O(l) F − (aq)

+0.15 +0.34 +0.40 +0.52 +0.54 +0.77 +0.80 +1.09 +1.23 +1.36 +1.36 +1.51 +2.87

23

25. Activity series

Increasing activity

Li Cs Rb K Ba Sr Ca Na Mg Be Al C

Zn Cr Fe Cd Co Ni Sn Pb H

Sb As Bi Cu Ag Pd Hg Pt Au

24

Chemistry data booklet

26. Infrared data

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

Organic molecules

C–Br

bromoalkanes

C–I

C–Cl C–F

C–O

C=C

iodoalkanes

chloroalkanes

600–800

1620–1680

hydrogen bonding in carboxylic acids

N–H

strong

alkenes

alcohols, esters, ethers

O–H O–H

500–600

490–620

1000–1400

aldehydes, ketones, carboxylic acids and esters

C–H

Intensity

fluoroalkanes

C=O C≡C

Wavenumber (𝐜𝐜𝐜𝐜−𝟏𝟏 )

alkynes

alkanes, alkenes, arenes

hydrogen bonding in alcohols and phenols primary amines

Chemistry data booklet

1050–1410

1700–1750 2100–2260

strong strong strong strong

medium-weak; multiple bands strong

variable

2500–3000

strong, very broad

3200–3600

strong, broad

2850–3090 3300–3500

strong

medium, two bands

25

27. 1H NMR data

Typical proton chemical shift values (𝛅𝛅) relative to tetramethylsilane (TMS) = 𝟎𝟎 .

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 CH3

CH2 R R2CH

C

0.9–1.0 1.3–1.4 1.5

O RO

Chemical shift (ppm)

CH2

2.0–2.5

O C

R

2.2–2.7

CH2

CH3

C C H

CH2 Hal

R O CH2 O R

C

O CH2

2.5–3.5 1.8–3.1 3.5–4.4 3.3–3.7 3.7–4.8

O R

C

O H

R O H

HC CH2

26

9.0–13.0 1.0–6.0 4.5–6.0

Chemistry data booklet

Type of proton

Chemical shift (ppm)

OH

4.0–12.0

H

6.9–9.0

O R

C

9.4–10.0

H

28. Mass spectral fragments lost Mass lost

Fragment lost

17

OH

15 18

H2 O

28

CH2 =CH2 , C=O

31

CH3 O

29 45

Chemistry data booklet

CH3

CH3 CH2 , CHO COOH

27

29. Triangular bonding diagram

van Arkel-Ketelaar Triangle of Bonding

Electronegativity difference 3.0

2.5

Electronegativity difference 𝚫𝚫𝚫𝚫 = |𝛘𝛘𝐚𝐚 − 𝛘𝛘𝐛𝐛 |

Ionic

2.0 1.5

Polar covalent

1.0 0.5 0

Metallic 0.79 1.0

1.5

Covalent 2.0

2.5

3.0

Average electronegativity ∑ 𝛘𝛘 =

28

% covalent % ionic

3.5

(𝛘𝛘𝐚𝐚 +𝛘𝛘𝐛𝐛 ) 𝟐𝟐

8

92

25

75

50

50

75

25

100

0

4.0

Chemistry data booklet

30. Resin identification codes Resin Identification Code (RIC)

Plastic types

Resin Identification Code (RIC)

Plastic types

polyethylene terephthalate

polypropylene

high-density polyethylene

polystyrene

polyvinyl chloride

other

low-density polyethylene

31. Representations of some materials molecules O

Clm

polychlorinated biphenyls

Cl

O O

1,4-dioxin

Clm

polychlorinated dibenzofuran O

Cl Cl

2,3,7,8-tetrachlorodibenzodioxin

Chemistry data booklet

O

O

Cln

Cl

Cln

Cln

Clm O

polychlorinated dibenzo-p-dioxin

29

32. Solubility product constants at 298 K Compound BaCO3

Ba(OH)2 ∙ 8H2 O

2.58 × 10−9

2.55 × 10−4

BaSO4

1.08 × 10−10

Cd(OH)2

7.2 × 10−15

CdCO3

1.0 × 10−12

PbCO3

7.40 × 10−14

PbSO4

2.53 × 10−8

Pb(OH)2 Hg 2 CO3 Hg 2 SO4 NiCO3

1.43 × 10−20 3.6 × 10−17 6.5 × 10−7

1.42 × 10−7

Ni(OH)2

5.48 × 10−16

Ag 2 SO4

1.20 × 10−5

Ag 2 CO3 ZnCO3

Zn(OH)2

30

𝑲𝑲𝐬𝐬𝐬𝐬

8.46 × 10−12 1.46 × 10−10 3.0 × 10−17

Chemistry data booklet

33. 2-amino acids Common name alanine

Symbol Ala

H2N CH COOH

H2N CH COOH

Arg

asparagine

Asn

H2N CH COOH

aspartic acid

Asp

H2N CH COOH

cysteine

Cys

H2N CH COOH

glutamic acid

Glu

H2N CH COOH

glutamine

Gln

H2N CH COOH

glycine

Gly

His

6.0

CH3

arginine

histidine

pH of isoelectric point

Structural formula

CH2 CH2 CH2 NH C NH2 NH

CH2 C NH2 O

CH2 COOH

CH2 SH

CH2 CH2 COOH CH2 CH2 C NH2 O H2N CH2 COOH

H2N CH COOH CH2

10.8 5.4 2.8 5.1 3.2 5.7 6.0 7.6

N N

isoleucine

Ile

leucine

Leu

Chemistry data booklet

H

H2N CH COOH H3C CH CH2 CH3

H2N CH COOH CH2 H3C CH CH3

6.0 6.0

31

Common name lysine

Symbol Lys

methionine

Met

phenylalanine

Phe

proline

Pro

serine

Ser

threonine

Thr

tryptophan

Trp

Structural formula

H2N CH COOH

CH2 CH2 CH2 CH2 NH2 H2N CH COOH CH2 CH2 S CH3 H2N CH COOH CH2

COOH HN

H2N CH COOH CH2 OH

H2N CH COOH H3C CH OH H2N CH COOH CH2

pH of isoelectric point 9.7 5.7 5.5

6.3 5.7 5.6 5.9

NH

tyrosine

Tyr

H2N CH COOH CH2

5.7

OH

valine

32

Val

H2N CH COOH H3C CH CH3

6.0

Chemistry data booklet

34. Lipids, carbohydrates and nucleotide components Lipids

Octanoic acid

CH3 (CH2 )6 COOH

Palmitic acid

CH3 (CH2 )14 COOH

CH3 (CH2 )10 COOH

Lauric acid

CH3 (CH2 )16 COOH

Stearic acid

CH3 (CH2 )7 CH=CH(CH2 )7 COOH

Oleic acid

CH3 (CH2 )4 (CH=CHCH2 )2 (CH2 )6 COOH

Linoleic acid

CH3 CH2 (CH=CHCH2 )3 (CH2 )6 COOH

α-Linolenic acid

CH3

H3C H CH2 CH3 CH2 C CH2 CH CH3 CH3

HO

Carbohydrates

cholesterol

H C O

CH2OH

H C OH

C O

HO C H

HO C H

H C OH

H C OH

H C OH

H C OH

CH2OH

CH2OH

straight chain glucose

Chemistry data booklet

α-glucose

straight chain fructose

33

CH2OH

CH2OH

O

H

OH

OH

H

H

OH

CH2OH H

H

OH

OH

H

H

fructose

ribose

Nitrogenous bases HC

C N

C

N

C N

NH

CH H

NH2

adenine

C

O

N C

C N H

uracil

34

C N

OH

O

H

H

OH

H

H

H

deoxyribose NH2

N

C

C N

CH H

guanine

O H

CH2OH

O

NH2

N

OH

O

N O

C

C N

CH CH

H

cytosine

O CH CH

H O

N C

C N

C

CH3

CH

H

thymine

Chemistry data booklet

35. Vitamins and pigments Vitamins

CH3

H C

CH3 CH

C

O O

CH3

CH

CH

CH

C

CH

CH2

HO

OH

CH3 CH3

CH HO

OH CH2

ascorbic acid (vitamin C)

retinol (vitamin A) CH3 CH3

CH2

OH

CH

CH2

CH2

CH2

CH CH3 CH3

CH CH2

HO

vitamin D (D3)

Chemistry data booklet

35

Pigments

CH2

R

CH

CH2

H 3C

N CH CH3

Mg

N

2+

CH2 C

CH2 O

O

CH

CH3

N

CH2 CH

CH

N CH3

CH3

CH3

CH3

N Fe2+

HC

C H O O

CH2 CH2

N

CH3

C20H39

O

CH2 CH2

CH3

N

H

H

O

N

OH HO

O

chlorophyll

CH2

CH

heme B R

R

OH O

O

OH O+

OH

R O glucose

O glucose

OH

OH

quinoidal base (blue) CH3

CH3

CH3 CH

CH

R

C

CH

flavylium cation (red) CH3

CH3 CH

CH

C

CH

CH

CH

CH

C

CH

CH3

CH3

CH

CH

C

CH

CH3

CH CH3

CH3

α-carotene

36

Chemistry data booklet

CH3

CH3

CH3

CH

C

CH

CH3

CH3

CH

CH

C

CH

CH

CH

CH

CH

C

CH

CH

CH

CH3

CH3

C

CH

CH3

CH CH3

CH3

β-carotene CH3

CH3 CH

CH

C

CH

CH3

CH H 3C

CH3

CH3 CH3 CH

CH C

CH

CH

CH

Average binding energy per nucleon (MeV) 7 6

5

CH

He

CH

C

CH

CH

O

all-trans-retinal

U235

Fe56

4

CH

O

36. Binding energy curve O16 8 C12

C

CH3

11-cis-retinal

9

CH3

CH3

U238

Li7 Li6

4

3

2

1

H3 He3 H2

1 0 H 0

30

Chemistry data booklet

60

90

120

150

180

210

240

270

Number of nucleons in nucleus

37

37. Representations of some medicinal molecules O C

R

OH

O

O C

CH3

C

CH2

CH3

NH

S N

O

O

CH3

H

N

C

O

CH3

ibuprofen

paracetamol (acetaminophen) OH

OH

CH2 CH2

H 3C N

O

CH2 CH2 O

OH

O

morphine O CH3

N

C

CH3

O

diamorphine (heroin)

38

NH CH3

O C

CH3

codeine

O

O

O

OH

H

C COOH

CH2 CH2

C

penicillin (general structure)

H

CH3 N

CH3 CH3

HO

aspirin CH3

C

O

N

O S

N CH3 CH3

CH3

O CH3

omeprazole

Chemistry data booklet

CH3

O

N

O–

NH

S

CH3

H 3C

N+

NH

O

ranitidine

O CH3

OH

O

NH2

O

NH

CH3

NH

O

O NH

O

CH3

OH

OH

CH3

NH

CH3

oseltamivir

OH NH2

O

zanamivir O CH3 O CH3 OH

O

O

NH

CH3 O O

OH

CH3 CH3 OH

O O

O

O

CH3 O

taxol

Chemistry data booklet

39

38. References

Data in sections 9, 10, 11, 12, 13, 22, 26 and 27 was taken fully or in part from:

Aylward, G and Findlay, T. 2008. SI chemical data. (5th edition). Queensland, Australia. John Wiley & Sons. Data in section 20 reproduced by permission of The Royal Society of Chemistry.

Barret, J. 2003. Inorganic chemistry in aqueous solution. London, UK. Royal Society of Chemistry.

Data in section 13 was taken in part from:

Burgess, DR. 2012. "Thermochemical Data". NIST Chemistry WebBook, NIST Standard Reference Database. Number 69. http://webbook.nist.gov.

Data in sections 7, 8, 9, 12, 13, 18, 19, 21, 23, 24, 28, 32, 33 was taken fully or in part from:

Haynes, WM, (ed). 2012. CRC Handbook of chemistry and physics. (93rd edition). Boca Raton, US. CRC Press.

Data in section 29 can be found in the following source:

Leach, MR. 2013. Timeline of structural theory. 04 January 2013. http://www.meta-synthesis.com/webbook/30_timeline/timeline.html.

40

Chemistry data booklet