Diploma Programme
Chemistry data booklet First examinations 2009
Diploma Programme Chemistry data booklet
First published March 2007 Revised edition published September 2008 International Baccalaureate Peterson House, Malthouse Avenue, Cardiff Gate Cardiff, Wales GB CF23 8GL United Kingdom Phone: +44 29 2054 7777 Fax: +44 29 2054 7778 Website: http://www.ibo.org © International Baccalaureate Organization 2008 The International Baccalaureate (IB) offers three high quality and challenging educational programmes for a worldwide community of schools, aiming to create a better, more peaceful world. The IB is grateful for permission to reproduce and/or translate any copyright material used in this publication. Acknowledgments are included, where appropriate, and, if notified, the IB will be pleased to rectify 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. General ordering queries should be directed to the sales and marketing department in Cardiff. Phone: +44 29 2054 7746 Fax: +44 29 2054 7779 Email:
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Printed in the United Kingdom by Antony Rowe Ltd, Chippenham, Wiltshire
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 = –
0 =
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
2
Element
Symbol
Atomic number
actinium aluminium americium antimony argon arsenic astatine barium berkelium beryllium bismuth bohrium boron bromine cium 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
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
5. The periodic table 1 1
2
3
3 4 5 6 7
5
6
7
1
0 2
H
He
Atomic number
1.01
2
4
3
4
Li
Be
6.94
9.01
4.00
Element Relative atomic mass
5
6
7
8
9
10
B
C
N
O
F
Ne
10.81
12.01
14.01
16.00
19.00
20.18
11
12
13
14
15
16
17
18
Na
Mg
Al
Si
P
S
Cl
Ar
22.99
24.31
26.92
28.09
30.97
32.06
35.45
39.95
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
K
Ca
Sc
Ti
V
Cr
Mn
Fe
Co
Ni
Cu
Zn
Ga
Ge
As
Se
Br
Kr
39.10
40.08
44.96
47.90
50.94
52.00
54.94
55.85
58.93
58.71
63.55
65.38
69.74
72.59
74.92
78.96
79.91
83.80
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
Rb
Sr
Y
Zr
Nb
Mo
Tc
Ru
Rh
Pd
Ag
Cd
In
Sn
Sb
Te
I
Xe
85.47
87.62
88.91
91.22
92.91
95.94
98.91
101.07
102.91
106.42
107.87
112.41
114.82
118.69
121.75
127.60
126.90
131.30
†
55
56
57
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
Cs
Ba
La
Hf
Ta
W
Re
Os
Ir
Pt
Au
Hg
Tl
Pb
Bi
Po
At
Rn
132.91
137.33
138.91
178.49
180.95
183.85
186.21
190.23
192.22
195.09
196.97
200.59
204.37
207.19
208.98
210
209.99
222.02
104
105
106
107
108
109
Rf
Db
Sg
Bh
Hs
Mt
262.11
266.12
264.12
269.13
268.13
‡
88
89
Ra
Ac
223.02
226.03
227.03
260 58
59
60
61
62
63
64
65
66
67
68
69
70
71
†
Ce
Pr
Nd
Pm
Sm
Eu
Gd
Tb
Dy
Ho
Er
Tm
Yb
Lu
140.12
140.91
144.24
144.91
150.35
151.96
157.25
158.93
162.50
164.93
167.26
168.93
173.04
174.97 103
‡
90
91
92
93
94
95
96
97
98
99
100
101
102
Th
Pa
U
Np
Pu
Am
Cm
Bk
Cf
Es
Fm
Md
No
Lr
232.04
231.04
238.03
239.05
239.05
243.06
247.07
247.07
252.08
254.09
253.09
257.10
255.09
257
3
Chemistry data booklet
87
Fr
14
1
H
He
Melting point / K
20 454
1551
Li
Be
1615
4
Element
2573
3925
63
55
53
25
B
C
N
O
F
Ne
3243
2823
5100
77
90
85
27
Boiling point / K
371
922
933
1683
317
392
172
84
Na
Mg
Si
P
S
Cl
Ar
1156
1380
Al 2740
2628
553
718
238
87
336
1112
1814
1933
2163
2130
1517
1808
1768
1728
1356
693
303
1210
1090
490
266
116
K
Sc
Ti
V
Cr
Mn
Fe
Co
Cu
Ga
Ge
As
Se
Br
Kr
1757
3104
3560
3653
2943
2235
3023
3143
Ni
Zn
1033
Ca
3003
2840
1180
2676
3103
886
958
332
121 161
312
1042
1795
2125
2740
2883
2445
2583
2239
1827
1235
594
429
505
904
723
387
Rb
Sr
Y
Zr
Ru
Rh
Cd
In
Te
I
Xe
4650
5015
5833
5150
4173
4000
3243
2485
1038
2353
Sn
Sb
3611
Pd
Ag
1657
Mo
Tc
959
Nb
2543
2023
1263
457
166
302
998
1194
2500
3269
3683
3453
2973
2683
2045
1337
234
577
601
544
527
575
202
Cs
Ba
La
Hf
Ta
Re
Pt
Au
Tl
Bi
Po
At
Rn
1913
5700
Ir
Pb
4875
Os
Hg
3730
W
5570
4403
4100
3353
1833
1235
610
211
300
973
1323
Fr
Ra
950
1413
942
Ac 3473
5933
5900
630
1730
2013
Chemistry data booklet
4
6. Melting points and boiling points of the elements
Chemistry data booklet
Chemistry data booklet
7. First ionization energy, electron affinity and electronegativity of the elements 1312
First ionization energy / Electron affinity / kJ mol –1 kJ mol–1 2nd EA / kJ mol –1
–73
H 2.2 520
900
801
Li
Be
1.0
1.6
–53
Na
Electronegativity
–27 1086 –122 1402
B 578
Mg
1.6 –2
631
–18 658
–8
650
–51
653
–64
717
759
–15
758
–64
737
–112 746
–119 906
579
N
2.6 –42 789
Al
1.3 –48 590
C
2.0
738
0.9 419
He
Element
–60
496
2372
–41 762
1314 –141 1681 –328 +798
3.0
–134 1012
Si
P
1.9
2.2
–119 947
O
F
3.4
4.0
–72 1000 –200 1251 –349 +640
Cl
S 2.6 –79 941
Ca
Sc
Ti
V
Cr
Mn
Fe
Co
Ni
Cu
Zn
Ga
Ge
As
Se
Br
0.8
1.0
1.4
1.5
1.6
1.7
1.6
1.8
1.9
1.9
1.9
1.7
1.8
2.0
2.2
2.6
3.0
47
550
–5
616
-30
660
–41
664
–86
685
–72 702
–53
711
–101
720
–110
805
–54
731
–126 868
558
–29 709
–107 834
–101 869
–190 1008 –295
Rb
Sr
Y
Zr
Nb
Mo
Tc
Ru
Rh
Pd
Ag
Cd
In
Sn
Sb
Te
I
0.8
1.0
1.2
1.3
1.6
2.2
2.1
2.2
2.3
2.2
1.9
1.7
1.8
2.0
2.1
2.1
2.7
376
–46
Cs
–14
Ba
0.8
0.9 –44
509
–10
538
–45
680
761
La
Hf
1.1
1.3
499 –34
Fr
Ra
Ac
0.7
0.9
1.1
–31
Ta 1.5
770
–79
W 1.7
760
–14
840
–106
880
–151
870 – 205 890
–223 1007
589
–19 716
–35 703
–91 812
–183
1521
Ar 1351
Kr 1170
Xe –270
Re
Os
Ir
Pt
Au
Hg
Tl
Pb
Bi
Po
At
1.9
2.2
2.2
2.2
2.4
1.9
1.8
1.8
1.9
2.0
2.2
1037
Rn
5
Chemistry data booklet
393
503
Ne
3.2
–195 1140 –325
K 403
2081
30
Atomic radius / 10–12 m
H 154 (1–) 152
Li 68 (1+) 186
Element 112
30 (2+)
98 (1+)
65 (2+)
244
94 (2+)
Sr
148 (1+)
110 (2+)
262
217
16 (3+)
45 (3+) 160
Sc 81 (3+) 180
Y 93 (3+) 188
Chemistry data booklet
Ba
La
167 (1+)
134 (2+)
115 (3+)
220
146
Ti 90 (2+) 68 (4+) 157
Zr
Cs 270
C
Al
215
Rb
77
260 (4–)
188
Fr
Ra
Ac
180 (1+)
148 (2+)
112 (3+)
80 (4+) 157
Hf 76 (4+)
131
V
125
Cr
88 (2+) 141
Nb 72 (3+) 64 (5+) 143
Ta 64 (5+) 72 (6+)
63 (3+) 136
Mo 68 (4+) 137
W 66 (4+) 42 (6+)
129
Mn 80 (2+) 60 (4+) 135
Tc 65 (4+) 37 (7+) 137
126
Fe 76 (2+) 64 (3+) 133
125
Co 74 (2+) 63 (3+) 134
124
Ni 72 (2+) 138
Ru
Rh
Pd
68 (3+) 62 (4+)
67 (3+) 60 (4+)
86 (2+) 62 (4+)
134
Re
Os
63 (4+) 38 (7+)
63 (4+) 39 (8+)
135
Ir 68 (3+) 63 (4+)
138
Pt 80 (2+) 63 (4+)
128
Cu 96 (1+) 69 (2+) 144
Ag 126 (1+) 144
133
141
Zn
Ga
74 (2+)
62 (3+)
149
Cd 97 (2+) 152
166
In 81 (3+) 171
70
N
Si 42 (4+) 271 (4–) 122
Ge 53 (4+) 272 (4–) 162
Sn 112 (2+) 71 (4+) 175
66
O
171 (3–)
117
143
197
Ca
133 (1+)
B
160
Mg
K
88
Ionic radius / 10–12 m
Be
Na 231
He
146 (2–)
S
212 (3–) 121
As 222 (3–) 141
Sb 245 (3–) 170
Au
Hg
Tl
Pb
Bi
137 (1+) 85 (3+)
127 (1+) 110 (2+)
150 (1+) 93 (3+)
120 (2+) 84 (4+)
120 (3+) 76 (5+)
F
Ne
133 (1–)
104
110
P
64
99
Cl
190 (2–)
181 (1–)
117
Se 202 (2–)
114
Br
222 (2–) 140
Po 94 (4+) 67 (6+)
Kr
196 (1–)
137
Te
Ar
133
I
Xe
219 (1–) 140
At 62 (7+)
Rn
Chemistry data booklet
6
8. Atomic and ionic radii of the elements
Chemistry data booklet
9. Covalent bond lengths Bond H–H C–C C=C CC C C (in benzene) Si–Si N–N N=N NN P–P O–O O=O S–S S=S F–F Cl–Cl Br–Br I–I
Bond length / nm
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 CN 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
0.161
10. Bond enthalpies and average bond enthalpies at 298 K Bond H–H C–C C=C CC C C (benzene) Si–Si N–N N=N NN P–P O–O O=O S–S F–F Cl–Cl Br–Br I–I
Chemistry data booklet
ΔH / kJ mol –1 436 347 612 838 505 226 158 410 945 198 144 498 266 158 243 193 151
Bond
ΔH / kJ mol –1
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 CN C–F C–Cl C–Br C–I
358 746 286 615 887 467 346 290 228
Si–O
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 Öf /
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 Öf /
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
Chemistry data booklet
12. Enthalpies of combustion The values of the molar enthalpy of combustion Formula
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
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
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
in the following table refer to a temperature of 298 K and a pressure of 1.01 × 105 Pa (1 atm).
H c / kJ mol–1 –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
Substance
Formula
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
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
State
H c / kJ mol–1
1 1 s s l g g l l l l l l s s l s g g l l s s s
–2021 –2676 –3727 –3053 –2724 –571 –1167 –3525 –1817 –3100 –4149 –254 –874 –3227 –243 –2238 –1185 –1085 –1740 –3393 –3088 –632 –2803 –5640
9
Chemistry data booklet
Substance
(H c )
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 / kJ mol–1 H lattice
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 / kJ mol–1 H lattice
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 of pKa values, where pKa = –log10 Ka. The dissociation constant Ka values are for aqueous solutions at 298 K. Base strengths are given in 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
methyl orange bromophenol blue bromocresol green methyl red bromothymol blue phenol red phenolphthalein
14
pKa
3.46 4.10 4.90 5.00 7.30 8.00 9.50
pH range
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
Colour change Acid
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
C–I
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
CC
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
primary amines
3300–3500
N–H
Chemistry data booklet
15
Chemistry data booklet
18. 1H NMR data Typical proton chemical shift values () 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 H
1.8–3.1
CH2 Hal
3.5–4.4
O
3.3–3.7
C
R
2.5–3.5
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
4.0–12.0
H
6.9–9.0
O R
16
C
H
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
COOH
CH 2 C
Asn
NH 2
5.4
O
aspartic acid
Asp
cysteine
Cys
glutamic acid
Glu
H 2N
COOH
CH 2 COOH H 2N
CH
COOH
CH2 SH H2N
CH
COOH
CH 2 CH2 COOH H 2N
glutamine
CH
CH
5.1 3.2
COOH
CH2 CH 2 C
Gln
2.8
NH2
5.7
O
glycine
Gly
H 2N
CH2 COOH
H2N
CH
6.0
COOH
CH 2
histidine
His
7.6
N N H
isoleucine
Ile
H 2N
CH
COOH
H3C
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
Phe
Structural formula 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
COOH
5.7 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
NH 2
CH3
HO
O
C
CH3
diamorphine (heroin)
OH
H
CH
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 HO
CH
I
H CH2
N
I
O
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