INTERNATIONAL BACCALAUREATE ORGANIZATION

CHEMISTRY DATA BOOKLET

August 2001

To be used in the teaching and examination ofDiploma Programme chemistry

Valid for examination sessions from May 2003

Chemistry Data BookletAugust 2001

© International Baccalaureate Organization 2001

International Baccalaureate OrganizationRoute des Morillons 15

1218 Grand - SaconnexGeneva, SWITZERLAND

Notes

This booklet cannot be used for paper 1 of the examination (HLP1 and SLP1), but the periodictable given on page 4 will be available as part of these examination papers. Clean copies of thisbooklet must be made available to candidates for papers 2 and 3 (HLP2, HLP3, SLP2 andSLP3).

Contents

1. Some Relevant Equations 2

2. Physical Constants 2

3. Fundamental Particles 2

4. Names of the First 103 Elements 3

5. The Periodic Table 4

6. Melting Points and Boiling Points of the Elements 5

7. First Ionization Energy, Electron Affinity and Electronegativity of the Elements 6

8. Atomic and Ionic Radii of the Elements 7

9. Covalent Bond Lengths 8

10. Average Bond Enthalpies at 298 K 8

11. Organic Compounds—Thermodynamic Data 9

12. Ellingham Diagram 10

13. Enthalpies of Combustion 11

14. Lattice Enthalpies at 298 K (Experimental and Theoretical Values) 12

15. Standard Electrode Potentials 13

16. Strengths of Organic Acids and Bases 14

17. Acid–base Indicators 15

18. Infrared Data 16

19. 1H NMR Data 17

20. 2-amino Acids 18

21. Structural Formulas of Some Important Medicines and Drugs 20

22. Structural Formulas of Some Important Biological Molecules 22

IB Diploma Programme Chemistry Data Booklet, August 2001 1

1. Some Relevant Equations

or[ ] [ ] ktoA A e−=

[ ][ ]

oln =A

ktA

aERTk Ae

−

= ln lnaE

k ART

= − +

Ilog

Io lc10 = ∈1

2

0.693t

k=

PV PVT T1 1 2 2

1 2

=G H T S∆ = ∆ − ∆0 0 0

E mc2=E hf=

2. Physical Constants

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, 1.01 × 105 Pa = 2.24 × 10-2 m3 mol-1 (22.4 dm3 mol-1)

Speed of light in a vacuum (c) = 3.00 × 108 m s-1

Planck 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 mol2 dm-6 at 298 K

(1 atm = 1.01 × 105 Pa)(1 dm3 = 1 litre = 1 × 10-3 m3 = 1 × 103 cm3)

3. Fundamental Particles

9.109534 × 10-31

1.602189 × 10-19

1.674954 × 10-27

0

1.672648 × 10-27

1.602189 × 10-19

Mass/kg

Charge/C

ElectronNeutronProton

IB Diploma Programme Chemistry Data Booklet, August 2001 2

4. Names of the First 103 Elements

804260109328417

10276846157894841959619188867545374462213414471138167343526581906950227492235470393040

HgMoNdNeNpNiNbN

NoOsOPdPPtPuPoKPrPmPaRaRnReRhRbRuSmScSeSiAgNaSrS

TaTcTeTbTlThTmSnTiWUVXeYbYZnZr

mercurymolybdenumneodymiumneonneptuniumnickelniobiumnitrogennobeliumosmiumoxygenpalladiumphosphorusplatinumplutoniumpoloniumpotassiumpraseodymiumpromethiumprotactiniumradiumradonrheniumrhodiumrubidiumrutheniumsamariumscandiumseleniumsiliconsilversodiumstrontiumsulfurtantalumtechnetiumtelluriumterbiumthalliumthoriumthuliumtintitaniumtungstenuraniumvanadiumxenonytterbiumyttriumzinczirconium

8913955118338556974835354855209865817242729966699686310098764313279722671495377263657103823711225101

AcAlAmSbArAsAtBaBkBeBiBBrCdCsCaCfCCeClCrCoCuCmDyEsErEuFmFFrGdGaGeAuHfHeHoHInIIrFeKrLaLrPbLiLuMgMnMd

actiniumaluminiumamericiumantimonyargonarsenicastatinebariumberkeliumberylliumbismuthboronbrominecadmiumcaesiumcalciumcaliforniumcarbonceriumchlorinechromiumcobaltcoppercuriumdysprosiumeinsteiniumerbiumeuropiumfermiumfluorinefranciumgadoliniumgalliumgermaniumgoldhafniumheliumholmiumhydrogenindiumiodineiridiumironkryptonlanthanumlawrenciumleadlithiumlutetiummagnesiummanganesemendelevium

AtomicNumber

SymbolElementAtomicNumber

SymbolElement

IB Diploma Programme Chemistry Data Booklet, August 2001 3

1 2 3 4 5 6 7 0

5. The Periodic Table

103Lr

(260)

102No

(259)

101Md

(258)

100Fm

(257)

99Es

(254)

98Cf

(251)

97Bk

(247)

96Cm

(247)

95Am

(243)

94Pu

(244)

93Np

(237)

92U

238.03

91Pa

231.04

90Th

232.04

‡

71Lu

174.97

70Yb

173.04

69Tm

168.93

68Er

167.26

67Ho

164.93

66Dy

162.50

65Tb

158.92

64Gd

157.25

63Eu

151.96

62Sm

150.35

61Pm

146.92

60Nd

144.24

59Pr

140.91

58Ce

140.12

†

89 ‡Ac

(227)

88Ra

(226)

87Fr

(223)

86Rn

(222)

85At

(210)

84Po

(210)

83Bi

208.98

82Pb

207.19

81Tl

204.37

80Hg

200.59

79Au

196.97

78Pt

195.09

77Ir

192.22

76Os

190.21

75Re

186.21

74W

183.85

73Ta

180.95

72Hf

178.49

57 †La

138.91

56Ba

137.34

55Cs

132.91

54Xe

131.30

53I

126.90

52Te

127.60

51Sb

121.75

50Sn

118.69

49In

114.82

48Cd

112.40

47Ag

107.87

46Pd

106.42

45Rh

102.91

44Ru

101.07

43Tc

98.91

42Mo

95.94

41Nb

92.91

40Zr

91.22

39Y

88.91

38Sr

87.62

37Rb

85.47

36Kr

83.80

35Br

79.90

34Se

78.96

33As

74.92

32Ge

72.59

31Ga

69.72

30Zn

65.37

29Cu

63.55

28Ni

58.71

27Co

58.93

26Fe

55.85

25Mn

54.94

24Cr

52.00

23V

50.94

22Ti

47.90

21Sc

44.96

20Ca

40.08

19K

39.10

18Ar

39.95

17Cl

35.45

16S

32.06

15P

30.97

14Si

28.09

13Al

26.98

12Mg

24.31

11Na

22.99

10Ne

20.18

9F

19.00

8O

16.00

7N

14.01

6C

12.01

5B

10.81

4Be

9.01

3Li

6.94

2He

4.00

Atomic Number

Element

Atomic Mass

1H

1.01

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4

6. Melting Points and Boiling Points of the Elements

1320

Ac

3470

973

Ra

1413

300 Fr

950

202

Rn

211

575

At

610

527

Po

1235

545

Bi

1833

601

Pb

2013

577

Tl

1730

234

Hg

630

1338

Au

3080

2045

Pt

4100

2683

Ir

4403

3327

Os

5300

3453

Re

5900

3680

W

5930

3269

Ta

5698

2503

Hf

5470

1194

La

3730

983

Ba

2023

302

Cs

952

161 Xe

166

387

I

458

723

Te

1263

904

Sb

2023

505

Sn

2543

429

In

2353

594

Cd

1038

1235

Ag

2485

1825

Pd

3413

2239

Rh

4000

2583

Ru

4173

2445 Tc

5150

2890

Mo

4885

2741 Nb

5015

2125

Zr

4650

1780 Y

3611

1042

Sr

1657

312

Rb

961

117 Kr

121

266

Br

332

490

Se

958

889

As

1211

Ge

3103

303

Ga

2676

693

Zn

1180

1357

Cu

2840

1726

Ni

3005

1768

Co

3143

1808

Fe

3023

1517

Mn

2235

2130

Cr

2755

1973

V

3650

1933

Ti

3560

1814

Sc

3104

1112

Ca

1757

337 K

1047

84

Ar

87

172

Cl

239

392

S

718

317

P

553

1683

Si

2628

936

Al

2740

922

Mg

1363

371

Na

1156

25

Ne

27

54

F

85

55 O

90

63

N

77

4100

C

5100

2573

B

3931

1551

Be

3243

454

Li

1600

1

He

4

M.pt/K

Element

B.pt/K

14

H

20

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7. First Ionization Energy, Electron Affinity and Electronegativity of the Elements

669

Ac

510

Ra

381

Fr

1040

Rn

920

At

2.2

812

Po

2.0

703

Bi

1.9

716

Pb

1.8

590

Tl

1.8

1010

Hg

1.9

891

Au

2.4

866

Pt

2.2

887

Ir

2.2

841

Os

2.2

762

Re

1.9

770

W

1.7

766

Ta

1.5

531

Hf

1.3

540

La

1.1

502

Ba

0.9

376

Cs

0.7

1170

Xe

1010 -314

I

2.5

870

Te

2.1

833

Sb

1.9

707

Sn

1.8

556

In

1.7

866

Cd

1.7

732

Ag

1.9

803

Pd

2.2

745

Rh

2.2

724

Ru

2.2

699

Tc

1.9

694

Mo

1.8

653

Nb

1.6

669

Zr

1.4

636

Y

1.2

548

Sr

1.0

402

Rb

0.8

1350

Kr

1140

-342

Br

2.8

941

Se

2.4

966

As

2.0

762

Ge

1.8

577

Ga

1.6

908

Zn

1.6

745

Cu

1.9

736

Ni

1.8

757

Co

1.8

762

Fe

1.8

716

Mn

1.5

653

Cr

1.6

648

V

1.6

661

Ti

1.5

632

Sc

1.3

590

Ca

1.0

418

K

0.8

1520

Ar

1260 -364

Cl

3.0

1000 -200 (S -

+532)

S2.5

1060 -70

P

2.1

786 -180

Si

1.8

577 -47

Al

1.5

736

Mg

1.2

494 -71

Na

0.9

2080

Ne

1680 -348

F

4.0

1310 -142 (O- +844)

O3.5

1400 -3

N

3.0

1090 -120

C

2.5

799 -29

B

2.0

Element

Electronegativity

900

Be

1.5

519 -52

Li

1.0

2370

He

Electronaffinity /kJ mol -1

First ionization energy / kJ mol -1

1310 -72

H

2.1

IB D

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6

1.10.90.7

760

8. Atomic and Ionic Radii of the Elements

200

220

Ra

270

Fr

Rn

140

At

140

Po

170

Bi

120 (3+)

175

Pb120 (2+) 84 (4+)

171

Tl

95 (3+)

152

Hg127 (1+)110 (2+)

144

Au137 (1+) 85 (3+)

138

Pt

135

Ir

66 (4+)

134

Os

67 (4+)

137

Re

137

W

68 (4+)

143

Ta

73 (5+)

157

Hf

81 (4+)

188

La

115 (3+)

217

Ba

34 (2+)

262

Cs

167 (1+)

Xe

133

I

219 (1-)

137

Te

222 (2-)

141

Sb

245 (3-)

162

Sn112 (2+)71 (4+)

166

In

81 (3+)

149

Cd

97 (2+)

144

Ag

126 (1+)

138

Pd

134

Rh

86 (2+)

133

Ru

65 (4+)

135

Tc

136

Mo

68 (4+)

141

Nb

70 (5+)

157

Zr

80 (4+)

180

Y

93 (3+)

215

Sr

110 (2+)

244

Rb

148 (1+)

Kr

114

Br

196 (1-)

117

Se

202 (2-)

121

As

222(3-)

122

Ge53 (4+)272 (4-)

141

Ga

62 (3+)

133

Zn

74 (2+)

128

Cu 96 (1+) 69 (2+)

124

Ni

72 (2+)

125

Co74 (2+) 63 (3+)

126

Fe76 (2+) 64 (3+)

129

Mn80 (2+) 60 (4+)

125

Cr

63 (3+)

131

V 88 (2+) 59 (5+)

146

Ti90 (2+)68 (4+)

160

Sc

81 (3+)

197

Ca

94 (2+)

231

K

133 (1+)

Ar

99

Cl

181 (1-)

104

S

190 (2-)

110

P

212 (3-)

117

Si42 (4+)271 (4-)

143

Al

45 (3+)

160

Mg

65 (2+)

186

Na

98 (1+)

Ne

58

F

133 (1-)

66

O

146 (2-)

70

N

171 (3-)

77

C

260 (4-)

88

B

16 (3+)

Element

Ionicradius/10-12 m

112

Be

30 (2+)

152

Li

68 (1+)

He

Atomic radius/ 10-12 m

30

H

154(1-)

IB D

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7

Ac

9. Covalent Bond Lengths

0.1090.1460.1010.1420.0960.1350.0920.1280.1410.160

0.1430.1220.1360.1470.1270.1160.1350.1380.1770.1690.1930.214

0.150

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

C–O C=O C–O (in phenol) C–N C=N ChN C–N (in phenylamine) C–F C–Cl C–Cl (in chlorobenzene) C–Br C–I

Si–O

0.0740.1540.1340.1200.1390.2350.1460.1200.1100.2210.1480.1210.2070.1880.1420.1990.2280.267

H–H C–C C=C ChC C–C (in benzene) Si–Si N–N N=N NhN P–P (P4) O–O O=O S–S (S8) S=S F–F Cl–Cl Br–Br I–I

Bond length/nm

BondBond length/nm

Bond

10. Average Bond Enthalpies at 298 K

412318388322463338562431366299

360743305613890484338276238

374

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

C–O C=O C–N C=N ChN C–F C–Cl C–Br C–I

Si–O

436442348612837518226188151163409944172146496264158242193151

H–H D–D C–C C=C ChC C–C (benzene) Si–Si Ge–Ge Sn–Sn N–N N=N NhN P–P O–O O=O S–S F–F Cl–Cl Br–Br I–I

∆H / kJ mol-1 Bond∆H / kJ mol-1 Bond

IB Diploma Programme Chemistry Data Booklet, August 2001 8

11. Organic Compounds—Thermodynamic Data

186230270310348387219267307301296201248279204269173320360345234179203246222163

276

264208314238127282161146219266295129160167

242285105

-51-33-24-16-80686372676420919415227130125122131214-59-63-72-26320

-53

52-8099

-162-166-169-175-51-110-134-152-346-392-245

2837-47

-75-85-104-125-146-16752201-6-10227185112-15683495030148-82-117-132-36-20-8

141-105-85-3131

-16652

-201-239-235-278-163-116-166-216-409-487-385-481-320-28-49-333

gggggggggggggglglggggllgllsgllglgglglsgggllslsggs

CH4C2H6C3H8C4H10C5H12C6H14C2H4C3H6C4H8 C4H8 C4H8C2H2C3H4C4H6 C6H12 C6H6C6H6C6H5CH3C6H5CH2CH3C6H5CHCH2CH3ClCH2Cl2CHCl3CH3BrCHBr3CH3ICHI3C2H5ClC2H5BrC2H5IC2H3ClCH2ClCH2ClC6H5ClCH3OHCH3OHC2H5OHC2H5OHC6H5OHHCHOCH3CHO(CH3)2COHCOOHCH3COOHC6H5COOHCH3COOC2H5CH3CONH2CH3NH2C2H5NH2CO(NH2)2

methaneethanepropanebutanepentanehexaneethenepropenebut-1-enecis-but-2-enetrans-but-2-eneethynepropynebuta-1,3-dienecyclohexanebenzene benzene methylbenzeneethylbenzenephenylethenechloromethanedichloromethanetrichloromethanebromomethanetribromomethaneiodomethanetriiodomethanechloroethanebromoethaneiodoethanechloroethene1,2-dichloroethanechlorobenzenemethanol methanol ethanol ethanol phenolmethanalethanalpropanonemethanoic acidethanoic acidbenzoic acidethyl ethanoateethanamidemethylamineethylamineurea

S0 / J K-1 mol-1∆Gf0 / kJ mol-1∆Hf0 / kJ mol-1State FormulaSubstance

IB Diploma Programme Chemistry Data Booklet, August 2001 9

12. Ellingham Diagram

Standard Gibbs free energy changes of formation, ∆G0f , for oxides given per mole of oxygen gas as afunction of temperature.

0

– 200

– 400

– 600

– 800

– 1000

– 1200

500 1000 1500 2000 2500

Ag

Hg

C

Pb

Fe

CO

Zn

Cr

Ti

Al

Mg

Ca

Pb

4Ag+O 2Ag

Od2 2

2Hg+O

2HgOd2

2Pb+O 2Pb

Od2

2Fe+O 2FeOd 2

2Zn+O

2ZnOd2

Cr+O C

r Od2

232

3–

43–

Al+O A

l Od2

2 323–

43–

2Mg+O

2MgOd2

2Ca+O

2CaOd2

Ti+O

TiOd22

2C+O 2COd 2

2CO+O

2COd2

2

C

Temperature / K

IB Diploma Programme Chemistry Data Booklet, August 2001 10

f /kJmolG−1∆ 0

2 2C O CO+ →C O CO+ →

13. Enthalpies of CombustionThe values of the molar enthalpy of combustion in the following table refer to a temperature of 298 K and a pressure of 1.01 × 105 Pa (1 atm).

-2010-2673-4056-3727-3064-2727-561-1167-3520-1786-3078-4138-6512-263-876-3227-246-2246-1182-3546-1072-1709-3397-3094-634-2816-5644

11ls

lgllllssllsslssggllsss

C3H7OHC4H9OHC6H5CH2OHC6H11OHC6H5OH(C2H5)2OHCHOCH3CHOC6H5CHO(CH3)2CO(C2H5)2COCH3COC6H5(C6H5)2COHCOOHCH3COOHC6H5COOH(COOH)2CH3COOC2H5

CH3CONH2C6H5CONH2CH3NH2C2H5NH2C6H5NH2C6H5NO2CO(NH2)2C6H12O6C12H22O11

propan-1-olbutan-1-olphenylmethanolcyclohexanolphenolethoxyethanemethanalethanalbenzaldehydepropanonepentan-3-onephenylethanonediphenylmethanonemethanoic acidethanoic acidbenzoic acidethanedioic acidethyl ethanoateethanamidebenzamidemethylamineethylaminephenylaminenitrobenzeneureaglucosesucrose

-286-297-394-395-283-890

-1560-2220-2877-3509-4194-5512-3924-1409-2542-1299-3273-3909-5157-7114-1325-1425-1490-3709-373-715

-1371

gssssgggggllllgggllssggllll

H2SCCCOCH4C2H6C3H8C4H10C5H12C6H14C8H18C6H12C2H4C4H6C2H2C6H6C6H5CH3C10H8C14H10C2H5ClC2H5BrC2H5IC6H5CH2ClCHCl3CH3OHC2H5OH

hydrogensulfur carbon (graphite)carbon (diamond)carbon monoxidemethaneethanepropanebutanepentanehexaneoctanecyclohexaneethenebuta-1,3-dieneethynebenzenemethylbenzenenaphthaleneanthracenechloroethanebromoethaneiodoethane(chloromethyl)benzenetrichloromethanemethanolethanol

/ kJ mol-1cH∆0State Formula Substance / kJ mol-1c( )H∆

0State Formula Substance

IB Diploma Programme Chemistry Data Booklet, August 2001 15

IB D

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11

c( )H∆0

14. Lattice Enthalpies at 298 K (Experimental and Theoretical Values)

The lattice enthalpy values given relate to the endothermic process inlattice( )H∆0

which the gaseous ions of a crystal are separated to an infinite distance from each other.

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

744684629609585

800733670647619

846771701675645

1022902801767716

Li Na K Rb Cs

IBrClF

/ kJ mol-1latticeH∆0Alkali metal halides

3238296627792643976955905890876640

MgS CaS SrS BaS CuCl AgF AgCl AgBr AgI NH4Cl

2602300624932237211220183889351333103152

CaF2 BeCl2 MgCl2 CaCl2 SrCl2 BaCl2 MgO CaO SrO BaO

/ kJ mol-1latticeH∆0Other substances/ kJ mol-1latticeH∆

0Other substances

Theoretical Values These two tables contain lattice enthalpies calculated from electrostatic principles on the basis ofa purely ionic model for the crystal.

728686632607582

787732665644611

833766690674636

1004891795761728

Li Na K Rb Cs

IBrClF

/ kJ mol-1latticeH∆0Alkali metal halides

870770758736

AgF AgCl AgBr AgI

26113929347732053042

CaF2 MgO CaO SrO BaO

/ kJ mol-1latticeH∆0Other substances/ kJ mol-1latticeH∆

0Other substances

IB Diploma Programme Chemistry Data Booklet, August 2001 12

MX(s) M (g) X (g)+ −→ +

15. Standard Electrode Potentials

+2.87F-(aq)lF2 (g) + e- +1.51Mn2+(aq) + 4H2O(l)lMnO4-(aq) + 8H+(aq) + 5e-+1.36Cl-(aq)l½Cl2(g) + e-+1.332Cr3+(aq) + 7H2O(l) lCr2O72-(aq) + 14H+(aq) + 6e-+1.23H2O(l)l½O2(g) + 2H+(aq) + 2e-+1.09Br-(aq)l½Br2 (l) + e-

+0.80Ag(s)lAg+(aq) + e-

+0.77Fe2+(aq)lFe3+(aq) + e-

+0.54I-(aq)l½I2(s) + e- +0.52Cu(s)lCu+(aq) + e- +0.402OH-(aq)l½O2(g) + H2O(l) + 2e- +0.34Cu(s)lCu2+(aq) + 2e-+0.17H2SO3(aq) + H2O(l)lSO42-(aq) + 4H+(aq) + 2e-+0.15Cu+(s)lCu2+(aq) + e-

0.00½H2(g)lH+(aq) + e--0.13Pb(s)lPb2+(aq) + 2e- -0.14Sn(s)lSn2+(aq) + 2e-

-0.23Ni(s)lNi2+(aq) + 2e- -0.44Fe(s)lFe2+(aq) + 2e- -0.76Zn(s)lZn2+(aq) + 2e--0.83½H2(g) + OH-(aq)lH2O(l) + e--1.18Mn(s) lMn2+(aq) + 2e--1.66Al(s)lAl3+(aq) + 3e--2.36Mg(s)lMg2+(aq) + 2e--2.71Na(s) lNa+(aq) + e--2.87Ca(s)lCa2+(aq) + 2e--2.92K(s)lK+(aq) + e--3.03Li(s)lLi+(aq) + e-

E0 / VOxidized species l Reduced species

IB Diploma Programme Chemistry Data Booklet, August 2001 13

16. Strengths of Organic Acids and Bases

The acid strengths in the following tables are given in terms of pKa values, where pKa = -log10 Ka.The dissociation constant, Ka, values are for aqueous solutions at 298 K. Base strengths are given in termsof pKb values.

Carboxylic Acids

3.754.764.874.824.854.865.054.204.31

HCOOHCH3COOHCH3CH2COOHCH3(CH2)2COOH(CH3)2CHCOOHCH3(CH2)3COOH(CH3)3CCOOHC6H5COOHC6H5CH2COOH

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

pKa Formula Name

Halogenated Carboxylic Acids

2.861.290.652.662.903.17

CH2ClCOOHCHCl2COOHCCl3COOHCH2FCOOHCH2BrCOOHCH2ICOOH

chloroethanoic dichloroethanoic trichloroethanoic fluoroethanoic bromoethanoic iodoethanoic

pKa Formula Name

Phenols

10.007.218.357.154.010.42

C6H5OHO2NC6H4OHO2NC6H4OHO2NC6H4OH(O2N)2C6H3OH(O2N)3C6H2OH

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

pKaFormula Name

Alcohols

15.516 (approximately)

CH3OHC2H5OH

methanol ethanol

pKaFormula Name

IB Diploma Programme Chemistry Data Booklet, August 2001 14

Amines

4.753.363.273.284.203.073.369.38

NH3CH3NH2CH3CH2NH2(CH3)2NH(CH3)3N(C2H5)2NH(C2H5)3NC6H5NH2

ammonia methylamine ethylamine dimethylamine trimethylamine diethylamine triethylamine phenylamine

pKbFormula Name

17. Acid–base Indicators

yellowblueblueyellowblueredred

redyellowyellowredyellowyellowcolourless

3.1–4.43.0–4.63.8–5.44.2–6.36.0–7.66.8–8.48.3–10.0

3.74.04.75.17.07.99.3

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

AlkaliAcidpH rangepKa Indicator

Colour change

IB Diploma Programme Chemistry Data Booklet, August 2001 15

18. Infrared Data

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

700 to 800

1000 to 1300

1610 to 1680

1680 to 1750

2070 to 2250

2500 to 3300

2840 to 3095

3230 to 3550

3350 to 3500

halogenoalkanes

alcohols, ethers, esters

alkenes

aldehydes, ketones, acids, esters

alkynes

“hydrogen bonded” in acids

alkanes, alkenes, arenes

“hydrogen bonded” in alcohols, phenols

primary amines

C–Cl

C–O

C=C

C=O

ChC

O–H

C–H

O–H

N–H

Wavenumber / cm-1Organic moleculesBond

IB Diploma Programme Chemistry Data Booklet, August 2001 16

19. 1H NMR DataTypical proton chemical shift values (δ ) relative to TMS = 0.(These values can vary slightly in different solvents.)

9.7R C

O

H

7.3H

7OH

4.9–5.9RHC CH2

0.5–6.5 (can vary considerably underdifferent conditions)

R O H

4.0–4.2O C

O

CH3

4.1

R O CH3

R C O CH2R

O

3.8R O CH3

3.2–3.7R CH2 Hal

2.6R C C H

2.3CH3

2.1

O

C

CH3R

2.0CH3 C

O

OR

2 R3CH

1.3R CH2 R

0.9R CH3

Chemical shift/ppmType of proton

IB Diploma Programme Chemistry Data Booklet, August 2001 17

R C

O

O

11.5

H

20. 2-amino Acids

7.6H2N CH COOH

CH2

N

NHHishistidine

6.0H2N CH2 COOHGlyglycine

3.2H2N CH COOH

CH2 CH2 COOH

Gluglutamic acid

5.7H2N CH COOH

CH2 CH2 C NH2

O

Glnglutamine

5.1H2N CH COOH

CH2 SH

Cyscysteine

2.8H2N CH COOH

CH2 COOH

Aspaspartic acid

5.4H2N CH COOH

CH2 C NH2

O

Asnasparagine

10.8H2N CH COOH

CH2 CH2 CH2 NH C NH2

NH

Argarginine

6.0H2N CH COOH

CH3

Alaalanine

pH ofisoelectric

point

Structural formulaSymbolCommon name

6.0H2N CH

CH

COOH

CH3 CH2 CH3

Ileisoleucine

IB Diploma Programme Chemistry Data Booklet, August 2001 23

IB Diploma Programme Chemistry Data Booklet, August 2001 18

6.0H2N CH COOH

CH CH3CH3

Valvaline

5.7H2N CH COOH

CH2 OH

Tyrtyrosine

5.9H2N CH COOH

CH2

NH

Trptryptophan

5.6H2N CH COOH

CH OHCH3

Thrthreonine

5.7H2N CH COOH

CH2 OH

Serserine

6.3N

COOHHProproline

5.5H2N CH COOH

CH2

Phephenylalanine

5.7H2N CH COOH

CH2 CH2 S CH3

Metmethionine

9.7H2N CH

CH2

COOH

CH2 CH2 CH2 NH2

Lyslysine

6.0H2N CH

CH2

COOH

CH CH3CH3

Leuleucine

pH ofisoelectric

point

Structural formulaSymbolCommon name

IB Diploma Programme Chemistry Data Booklet, August 2001 19

21. Structural Formulas of Some Important Medicines and Drugs

aspirin paracetamol (acetaminophen) ibuprofen

morphine codeine heroin

amphetamine adrenaline caffeine nicotine

penicillin diazepam (valium®) nitrazepam (mogadon®)

IB Diploma Programme Chemistry Data Booklet, August 2001 20

O

COH

CCH3

O

O

CH2

C

C

CH3

H

CH3

COOH

H

CH3

OH

NHCOCH 3

OH

N

OH

CH2CH3

O

CH2

N

N

CH3

OCCH3

N

OCCH3

CH2CH3

O

CH2

O

OO

OH

N

OCH3

CH2CH3

O

CH2

R C

O

NH

N

O

S

CH3

CH3

C O

OH

N

N N

N

O

O

H3C

CH3

CH3

Cl N

NO

CH3

HO

HO CH

OH

NH CH3CH2CH2

CH3

NH2CH

O2N N

NO

CH3

cocaine acyclovir

cisplatin Lidocaine lysergic acid diethylamide (LSD)

mescaline

psilocybin

procaine

tetrahydrocannabinol (THC) fluoxetine hydrochloride (prozac®)

indole

IB Diploma Programme Chemistry Data Booklet, August 2001 21

Pt

Cl

NH3

NH3

Cl

O

O

NCH3

OCH3

N

HN

O

N

N

CH2O

H2N

CH2CH2

HO

CH3

NH

CH3

C CH2

N

CH2H2C

CH3CH3

ON

CH2N

CH3

CH3

CH2

O

NH

CH3

CH3O

CH3O

OCH3

CH2CH2

NH2

O

N

CH2CH2

N+

H

CH3

CH3H

P OO-

O

H

NH2 C O CH2CH2 N

CH2CH3

CH2CH3

O

CH3

O CH2CH2

CH2CH2

CH3

OH

H3C

H3C

O

F3C

CH2CH2

NH2 + Cl-

CH2

NH

22. Structural Formulas of Some Important Biological Molecules

lactose sucrose

ascorbic acid

(vitamin C)

oestradiol progesterone testosterone

IB Diploma Programme Chemistry Data Booklet, August 2001 22

C

CC

C

C

C

C

C

C

C

OH

C

H2C

H2C

C

C CH3

CH3

H H H H

H2

CH3 CH3 CH3H H H2

retinol (vitamin A)

O

H

OH

OH

H

H

CH2OH

H

HOO

H

OH

OH

HOH

HH

CH2OH

H

O

H

1

2

1

23

4

OH

H

OH

OH

H

H

CH2OH

HO

H

OH

H

1

2

O

O

HOCH2

1 2

3 4CH2OH

H

H

HO

CH3

CH3

CH

HO

H3C CH2

CH2

CH2

CH

CH3

CH3

CH3

CH

HO

H3C CH2

CH2

CH2

CH

CH3

CH2

CH3

C

O

C

C

C

C

CH2OH

HO

HO

H

HO H

O

CH3 OH

HO O

CH3 OH

CH3

CH3 C

H3C

O

O

CH3

cholesterol

vitamin D

adrenaline thyroxine

adenine guanine cytosine uracil thymine

adenosine triphosphate (ATP)

IB Diploma Programme Chemistry Data Booklet, August 2001 23

HO

HO CH

OH

CH2 NH CH3

I

HO

I

O

I

I

CH2 CH COOH

NH2

N

CN

C

CC

N

CH

N

O

H

H

H2N

N

CN

CH

CHC

H

O

NH2

N

CN

CH

CHC

H

O

H

O

N

CN

CH

CC

H

O

H

O

CH3N

HCN

C

CC

N

CH

N

NH2

H

O

OHOH

CH2OPOPOP

OOO

O–O–O–

N

N N

N

NH2

O–

Fe

N

N N

N

CH3

CH2CH2

C

H3C

CH2 CH3

CH

CH2HOOC

O

H

CH2

CH2 COOH

CH2HO

CH2CH

CCH2

CH2CH

C

CH2

CH2CH

C

CH3

CH3CH3 CH3

The haem group from cytochrome oxidase

IB Diploma Programme Chemistry Data Booklet, August 2001 30