Chemistry data booklet First assessment 2016 Edited in 2014 (version 2)
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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 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. 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Email: sales@ibo.org International Baccalaureate, Baccalauréat International and Bachillerato Internacional are registered trademarks of the International Baccalaureate Organization. 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 ๐๐๐๐ = ๐๐๐๐๐๐ 5.1 ๐๐ = ๐๐๐๐โ๐๐ 2.2 and C.4 8.3 12.1 15.2 16.2 ๐๐ = ๐ฃ๐ฃ๐ฃ๐ฃ ๐๐๐๐ = − log10 [H3 O+ ] or ๐๐๐๐ = −log10 [H + ] ๐ธ๐ธ = โ๐ฃ๐ฃ โ๐บ๐บ แด = โ๐ป๐ป แด − ๐๐โ๐๐ แด −๐ธ๐ธ๐๐ ๐๐ = ๐ด๐ด๐๐ ๐ ๐ ๐ ๐ 16.2 16.2 17.1 19.1 A.5 A.8 B.7 B.7 Chemistry data booklet ln ๐๐ = ln −๐ธ๐ธ๐๐ + ln ๐ด๐ด ๐ ๐ ๐ ๐ ๐๐1 ๐ธ๐ธ๐๐ 1 1 = ๏ฟฝ − ๏ฟฝ ๐๐2 ๐ ๐ ๐๐2 ๐๐1 โ๐บ๐บ แด = −๐ ๐ ๐ ๐ ln ๐พ๐พ % atom economy = โ๐บ๐บ แด = −๐๐๐๐๐๐ แด molar mass of desired product × 100 molar mass of all reactants ๐๐๐๐ = 2๐๐sin๐๐ ๐๐๐๐ = ๐๐๐พ๐พ๐๐ + log ๏ฟฝ log10 [๐ด๐ด− ] ๏ฟฝ [๐ป๐ป๐ป๐ป] ๐ผ๐ผ0 = ๐๐๐๐๐๐ ๐ผ๐ผ 1 Topic Equation C.1 Energy density = C.1 Speci๏ฟฝic energy = C.3 energy released from fuel mass of fuel consumed ๐๐ = ๐๐0 ๐๐ −๐๐๐๐ C.3 and D.8 C.6 energy released from fuel volume of fuel consumed ๐ก๐ก1 = 2 ln 2 ๐๐ ๐ธ๐ธ = ๐ธ๐ธ 0 − ๏ฟฝ C.7 D.8 ๐ ๐ ๐ ๐ ๏ฟฝ ln ๐๐ ๐๐๐๐ Rate1 ๐๐2 =๏ฟฝ Rate2 ๐๐1 ๐ก๐ก ๐๐๐ก๐ก = ๐๐0 (0.5) ๏ฟฝ๐๐ 2. Physical constants and unit conversions Avogadro’s constant (๐ฟ๐ฟ or ๐๐๐ด๐ด ) = 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) = 6.63 × 10−34 J s Faraday’s constant (๐น๐น) = 9.65 × 104 C mol−1 Ionic product constant for water (๐พ๐พw ) = 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 1312 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 (๐๐๐๐−๐๐๐๐ ๐ฆ๐ฆ = ๐ฉ๐ฉ๐ฉ๐ฉ) 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 (๐๐๐๐−๐๐๐๐ ๐ฆ๐ฆ = ๐ฉ๐ฉ๐ฉ๐ฉ) 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 (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) 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 (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) 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 โ๐ฏ๐ฏแด๐๐ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) −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 โ๐ฎ๐ฎแด๐๐ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) ๐บ๐บแด (๐๐ ๐๐ −๐๐ ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) +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(โ๐ป๐ป๐๐แด ) 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 โ๐ฏ๐ฏแด๐๐ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) −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 โ๐ฏ๐ฏแด๐๐ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) −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) แด The lattice enthalpy values (โ๐ป๐ปlattice ) 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 โ๐ฏ๐ฏแด๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) Other substances โ๐ฏ๐ฏแด๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) BeCl2 3033 BaO 3054 CaF2 MgCl2 CaCl2 SrCl2 BaCl2 MgO CaO 16 F โ๐ฏ๐ฏแด๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ๐ฅ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) 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 โ๐ฏ๐ฏแด๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) Solute โ๐ฏ๐ฏแด๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ๐ฌ (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) 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 โ๐ฏ๐ฏแด๐ก๐ก๐ก๐ก๐ก๐ก (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) Anions โ๐ฏ๐ฏแด๐ก๐ก๐ก๐ก๐ก๐ก (๐ค๐ค๐ค๐ค ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ๐ฆ−๐๐ ) 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 p๐พ๐พa values, where p๐พ๐พa = −log10 ๐พ๐พa . The dissociation constant ๐พ๐พa values are for aqueous solutions at 298 K . Base strengths are given in terms of p๐พ๐พb 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 ๐ฉ๐ฉ๐ฒ๐ฒ๐๐ 2.87 CCl3 COOH 0.66 CH2 FCOOH iodoethanoic CH2 ICOOH Chemistry data booklet 4.76 CH2 ClCOOH fluoroethanoic bromoethanoic ๐ฉ๐ฉ๐ฒ๐ฒ๐๐ 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 ๐ฉ๐ฉ๐ฒ๐ฒ๐๐ 7.23 7.15 4.07 0.42 ๐ฉ๐ฉ๐ฒ๐ฒ๐๐ CH3 OH 15.5 Name Formula ๐ฉ๐ฉ๐ฒ๐ฒ๐๐ 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 ๐ฉ๐ฉ๐ฒ๐ฒ๐๐ 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 (°๐๐) 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 ๐ฒ๐ฒ๐ฐ๐ฐ 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 ๐ฌ๐ฌแด (๐๐) 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 ๐ฌ๐ฌแด (๐๐) 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 (๐๐๐๐−๐๐ ) 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 (๐ ๐ ) relative to tetramethylsilane (TMS) = ๐๐ . 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 ๐ซ๐ซ๐ซ๐ซ = |๐๐๐๐ − ๐๐๐๐ | 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 ∑ ๐๐ = 28 % covalent % ionic 3.5 (๐๐๐๐ +๐๐๐๐ ) ๐๐ 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 โ 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 ๐ฒ๐ฒ๐ฌ๐ฌ๐ฌ๐ฌ 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
