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data booklet 2016

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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
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United Kingdom
Website: www.ibo.org
© International Baccalaureate Organization 2014
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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
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).
1. Some relevant equations
Topic
Equation
1.3
๐‘ƒ๐‘ƒ๐‘ƒ๐‘ƒ = ๐‘›๐‘›๐‘›๐‘›๐‘›๐‘›
5.1
๐‘ž๐‘ž = ๐‘š๐‘š๐‘š๐‘šโˆ†๐‘‡๐‘‡
2.2 and C.4
8.3
12.1
15.2
16.2
๐‘๐‘ = ๐‘ฃ๐‘ฃ๐‘ฃ๐‘ฃ
๐‘๐‘๐‘๐‘ = − log10 [H3 O+ ]
or
๐‘๐‘๐‘๐‘ = −log10 [H + ]
๐ธ๐ธ = โ„Ž๐‘ฃ๐‘ฃ
โˆ†๐บ๐บ แด = โˆ†๐ป๐ป แด − ๐‘‡๐‘‡โˆ†๐‘†๐‘† แด
−๐ธ๐ธ๐‘Ž๐‘Ž
๐‘˜๐‘˜ = ๐ด๐ด๐‘’๐‘’ ๐‘…๐‘…๐‘…๐‘…
16.2
16.2
17.1
19.1
A.5
A.8
B.7
B.7
ln ๐‘˜๐‘˜ =
ln
−๐ธ๐ธ๐‘Ž๐‘Ž
+ ln ๐ด๐ด
๐‘…๐‘…๐‘…๐‘…
๐‘˜๐‘˜1
๐ธ๐ธ๐‘Ž๐‘Ž 1
1
=
๏ฟฝ − ๏ฟฝ
๐‘˜๐‘˜2
๐‘…๐‘… ๐‘‡๐‘‡2 ๐‘‡๐‘‡1
โˆ†๐บ๐บ แด = −๐‘…๐‘…๐‘…๐‘… ln ๐พ๐พ
% atom economy =
โˆ†๐บ๐บ แด = −๐‘›๐‘›๐‘›๐‘›๐‘›๐‘› แด
molar mass of desired product
× 100
molar mass of all reactants
๐‘›๐‘›๐‘›๐‘› = 2๐‘‘๐‘‘sin๐œƒ๐œƒ
๐‘๐‘๐‘๐‘ = ๐‘๐‘๐พ๐พ๐‘Ž๐‘Ž + log ๏ฟฝ
log10
[๐ด๐ด− ]
๏ฟฝ
[๐ป๐ป๐ป๐ป]
๐ผ๐ผ0
= ๐œ€๐œ€๐œ€๐œ€๐œ€๐œ€
๐ผ๐ผ
Topic
Equation
C.1
Energy density =
C.1
Speci๏ฟฝic energy =
C.3
energy released from fuel
mass of fuel consumed
๐‘๐‘ = ๐‘๐‘0 ๐‘’๐‘’ −๐œ†๐œ†๐œ†๐œ†
C.3 and D.8
C.6
energy released from fuel
volume of fuel consumed
๐‘ก๐‘ก1 =
2
ln 2
๐œ†๐œ†
๐ธ๐ธ = ๐ธ๐ธ 0 − ๏ฟฝ
C.7
D.8
๐‘…๐‘…๐‘…๐‘…
๏ฟฝ ln ๐‘„๐‘„
๐‘›๐‘›๐‘›๐‘›
Rate1
๐‘€๐‘€2
=๏ฟฝ
Rate2
๐‘€๐‘€1
2. Physical constants and unit conversions
Avogadro’s constant (๐ฟ๐ฟ or ๐‘๐‘๐ด๐ด ) = 6.02 × 1023 mol−1
Gas constant (๐‘…๐‘…) = 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 (โ„Ž) = 6.63 × 10−34 J s
Faraday’s constant (๐น๐น) = 9.65 × 104 C mol−1
Ionic product constant for water (๐พ๐พw ) = 1.00 × 10−14 mol2 dm−6 at 298 K
1 amu = 1.66 × 10−27 kg
๐‘ก๐‘ก
๐‘๐‘๐‘ก๐‘ก = ๐‘๐‘0 (0.5) ๏ฟฝ๐‘˜๐‘˜
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)
Proton
Neutron
Electron
1.602189 × 10−19
0
−1.602189 × 10−19
1.672622 × 10−27
1.674927 × 10−27
9.109383 × 10−31
5. Names of the elements
Element
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
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
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
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)
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
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
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
10. Covalent bond lengths
Single bonds (๐Ÿ๐Ÿ๐Ÿ๐Ÿ−๐Ÿ๐Ÿ๐Ÿ๐Ÿ ๐ฆ๐ฆ = ๐ฉ๐ฉ๐ฉ๐ฉ)
Br
C
Cl
F
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 (๐Ÿ๐Ÿ๐Ÿ๐Ÿ−๐Ÿ๐Ÿ๐Ÿ๐Ÿ ๐ฆ๐ฆ = ๐ฉ๐ฉ๐ฉ๐ฉ)
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=C 134
C≡N 116
N≡N 110
C C
140
(in benzene)
C=S 156
O=O 121
C≡C 120
C=N 130
C=O 122
N=N 125
Si
220
148
154
S
N=O 114
S=S 189
185
156
148
243
174
163
215
232
11. Bond enthalpies and average bond enthalpies at 298 K
Single bonds (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
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 (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
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
C=O 804
N=N 470
307
597
323
234
466
C=C 614
C≡C 839
Si
N=O 587
S=S 429
293
226
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
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
โˆ†๐‘ฏ๐‘ฏแด๐Ÿ๐Ÿ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
−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
โˆ†๐‘ฎ๐‘ฎแด๐Ÿ๐Ÿ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
๐‘บ๐‘บแด (๐‰๐‰ ๐Š๐Š −๐Ÿ๐Ÿ ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
+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
13. Enthalpies of combustion
The values of the molar enthalpy of combustion(โˆ†๐ป๐ป๐‘๐‘แด ) 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
โˆ†๐‘ฏ๐‘ฏแด๐œ๐œ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
−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
โˆ†๐‘ฏ๐‘ฏแด๐œ๐œ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
−2021
−2676
−3728
−3053
−2724
−571
−1167
−3525
−1790
−3100
−4149
−255
−874
−3228
−243
−2238
−1186
−1086
−3393
−3088
−633
−2803
−5640
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
16. Ligands
NH2
NH2
1,2-ethanediamine
HO
N
O
O
O
O
HO
N
O–
HO
O–
ethanedioate
OH
EDTA
17. Colour wheel
647 nm
700 nm
400 nm
O
O
Orange
585 nm
Red
Yellow
Violet
Green
424 nm
Blue
491 nm
575 nm
18. Lattice enthalpies at 298 K (experimental values)
แด
The lattice enthalpy values (โˆ†๐ป๐ปlattice
) 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
F
Cl
โˆ†๐‘ฏ๐‘ฏแด๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
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
โˆ†๐‘ฏ๐‘ฏแด๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
Other substances
โˆ†๐‘ฏ๐‘ฏแด๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
BeCl2
3033
BaO
3054
CaF2
MgCl2
CaCl2
SrCl2
BaCl2
MgO
CaO
2651
SrO
2540
CuCl2
2170
AgCl
2271
2069
3791
3401
AgF
AgBr
AgI
3223
2824
974
918
905
892
19. Enthalpies of aqueous solutions
Solute
โˆ†๐‘ฏ๐‘ฏแด๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
Solute
โˆ†๐‘ฏ๐‘ฏแด๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
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
+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
20. Enthalpies of hydration
Cations
โˆ†๐‘ฏ๐‘ฏแด๐ก๐ก๐ก๐ก๐ก๐ก (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
Anions
โˆ†๐‘ฏ๐‘ฏแด๐ก๐ก๐ก๐ก๐ก๐ก (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐Ÿ๐Ÿ )
Na+
−424
Cl−
−359
Li+
K+
Rb+
Cs +
−538
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+
−1963
−1483
−1335
IO−
3
OH−
NO−
3
−4741
HCO−
3
−4171
HSO−
4
−346
PO3−
4
−4745
−4163
−1587
−1523
−504
−328
−287
−331
−358
−446
−205
−519
−341
−316
−383
CO2−
3
−1486
SO2−
4
−1099
−362
−2921
21. Strengths of organic acids and bases
The acid strengths in the following tables are given in terms of p๐พ๐พa values, where p๐พ๐พa = −log10 ๐พ๐พa .
The dissociation constant ๐พ๐พa values are for aqueous solutions at 298 K . Base strengths are given in terms of p๐พ๐พb
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
4.76
4.83
4.84
4.83
5.03
4.20
4.31
๐ฉ๐ฉ๐‘ฒ๐‘ฒ๐š๐š
CH2 ClCOOH
2.87
CCl3 COOH
0.66
fluoroethanoic
CH2 FCOOH
iodoethanoic
CH2 ICOOH
bromoethanoic
๐ฉ๐ฉ๐‘ฒ๐‘ฒ๐š๐š
CH2 BrCOOH
1.35
2.59
2.90
3.18
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
๐ฉ๐ฉ๐‘ฒ๐‘ฒ๐š๐š
7.23
7.15
4.07
0.42
๐ฉ๐ฉ๐‘ฒ๐‘ฒ๐š๐š
CH3 OH
15.5
Name
Formula
๐ฉ๐ฉ๐‘ฒ๐‘ฒ๐›๐›
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
15.5
(C2 H5 )2 NH
C6 H5 NH2
3.34
3.27
4.20
3.16
3.25
9.13
22. Acid-base indicators
Colour change
Indicator
๐ฉ๐ฉ๐‘ฒ๐‘ฒ๐š๐š
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
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
23. Values of the ionization constant of water
Temperature (°๐‚๐‚)
๐‘ฒ๐‘ฒ๐ฐ๐ฐ value
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
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
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
๐‘ฌ๐‘ฌแด (๐•๐•)
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
๐‘ฌ๐‘ฌแด (๐•๐•)
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
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
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 (๐œ๐œ๐œ๐œ−๐Ÿ๐Ÿ )
alkynes
alkanes, alkenes, arenes
hydrogen bonding in alcohols and phenols
primary amines
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
27. 1H NMR data
Typical proton chemical shift values (๐›…๐›…) relative to tetramethylsilane (TMS) = ๐ŸŽ๐ŸŽ .
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
9.0–13.0
1.0–6.0
4.5–6.0
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
CH3
H2 O
28
CH2 =CH2 , C=O
31
CH3 O
29
45
CH3 CH2 , CHO
COOH
29. Triangular bonding diagram
van Arkel-Ketelaar
Triangle of Bonding
Electronegativity
difference
3.0
2.5
Electronegativity
difference
๐šซ๐šซ๐šซ๐šซ = |๐›˜๐›˜๐š๐š − ๐›˜๐›˜๐›๐› |
Ionic
2.0
1.5
Polar
covalent
1.0
0.5
0
% covalent
% ionic
Metallic
0.79 1.0
1.5
Covalent
2.0
2.5
3.0
Average electronegativity ∑ ๐›˜๐›˜ =
3.5
(๐›˜๐›˜๐š๐š +๐›˜๐›˜๐›๐› )
๐Ÿ๐Ÿ
8
92
25
75
50
50
75
25
100
0
4.0
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
Clm
O
Cln
Cl
Cln
O
O
1,4-dioxin
polychlorinated dibenzofuran
O
Cl
Cl
2,3,7,8-tetrachlorodibenzodioxin
Cln
Clm
O
polychlorinated dibenzo-p-dioxin
32. Solubility product constants at 298 K
Compound
BaCO3
Ba(OH)2 โˆ™ 8H2 O
๐‘ฒ๐‘ฒ๐ฌ๐ฌ๐ฌ๐ฌ
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
8.46 × 10−12
1.46 × 10−10
3.0 × 10−17
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
H
H2N CH COOH
H3C CH CH2 CH3
H2N CH COOH
CH2
H3C CH CH3
6.0
6.0
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
Val
H2N CH COOH
H3C CH CH3
6.0
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
α-glucose
straight chain fructose
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
C
N
H
H
OH
H
H
H
NH2
N
C
C N
CH
H
CH
CH
O
N
C
C
N
C
N
O
C
C
N
CH
CH
H
cytosine
O
H
OH
O
deoxyribose
guanine
O
H
CH2OH
O
NH2
N
OH
O
CH3
CH
H
thymine
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)
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
α-carotene
CH
CH
C
CH
CH3
CH
CH3
CH3
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
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
60
90
120
150
180
Number of nucleons in nucleus
210
240
270
C
CH
CH
O
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)
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
omeprazole
O CH3
CH3
O
N
O–
NH
S
CH3
H 3C
N+
NH
O
ranitidine
O
CH3
OH
O
NH2
O
NH
CH3
NH
CH3
OH
OH
CH3
O
O
NH
O
NH
CH3
oseltamivir
OH
NH2
zanamivir
O
CH3
O
CH3 OH
O
O
NH
CH3
O
O
OH
CH3
CH3
OH
O
O
taxol
O
O
CH3
O
O
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.
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