Periodic Table. 8/3/2006 MEDC 501 Fall
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1 Periodic Table 8/3/2006 MEDC 501 Fall
2 rbitals Shapes of rbitals s - orbital p -orbital 8/3/2006 MEDC 501 Fall
3 Ionic Bond - acl Electronic Structure 11 a :: 1s 2 2s 2 2p x2 2p y2 2p z2 3s 1 11 a + :: 1s 2 2s 2 2p x2 2p y2 2p z2 3s 0 = 10 e 17 Cl - :: 1s 2 2s 2 2p x2 2p y2 2p z2 3s 1 3p x2 3p y2 3p z 2 = 18 Ar 17 Cl :: 1s 2 2s 2 2p x2 2p y2 2p z2 3s 1 3p x2 3p y2 3p z 1 8/3/2006 MEDC 501 Fall
4 Electronic Structure Can 6 C form ionic bonds? 6 C :: 1s 2 2s 2 2p x1 2p y 1 8/3/2006 MEDC 501 Fall
5 s -orbital ybridization + sp -orbital p -orbital n A give n 8/3/2006 MEDC 501 Fall
6 ybridization in Carbon sp 3 hybridization C 4 6 C :: 1s 2 2s 2 2p x1 2p y 1 6 C :: 1s 2 2s 1 2p x1 2p y1 2p z 1 1 :: 1s 1 6 C :: 1s 2 2sp x2 2sp y2 2sp z 2 8/3/2006 MEDC 501 Fall
7 ybridization in Carbon sp 2 hybridization C 2 =C 2 6 C :: 1s 2 2s 2 2p x1 2p y 1 6 C :: 1s 2 2s 1 2p x1 2p y1 2p z 1 8/3/2006 MEDC 501 Fall
8 ybridization in Carbon sp 2 hybridization C 2 =C 2 8/3/2006 MEDC 501 Fall
9 ybridization in Carbon sp hybridization C=C 6 C :: 1s 2 2s 2 2p x1 2p y 1 6 C :: 1s 2 2s 1 2p x1 2p y1 2p z 1 sp hybrid orbital π orbitals σ orbitals p orbitals 8/3/2006 MEDC 501 Fall
10 ybridization in Carbon sp 2 hybridization benzene C 6 6 8/3/2006 MEDC 501 Fall
11 Are all bonds same? Bond Polarity 3 C C 3 versus 3 C 8/3/2006 MEDC 501 Fall
12 Electronegativity Electronegativity: The ability of certain atoms to draw sigma electrons to themselves 8/3/2006 MEDC 501 Fall
13 Quantitative Measure of Electronegativity Sanderson Scale F 4.000, Cl 3.475, Br 3.219, I , 3.194, S C 2.746, Pauling Scale F 4.0, Cl 3.0, Br 2.8, I , 3.0, S 2.5 C 2.5, 2.1 Kier-all Scale χ = (column # - # of σ bonds) (row #) 2 8/3/2006 MEDC 501 Fall
14 Calculating Kier-all Electronegativity χ = b a (column # - # of σ bonds) (row #) 2 c d Cl e f g h C F 3 15 P 16 S 17 Cl 4 34 Se 35 Br 5 53 I 8/3/2006 MEDC 501 Fall
15 Dipolar Bonding Consequences of Bond Polarity C 3 3 C C 3 3 C 3 C 3 C C 3 3 C 3 C C C 3 2 C C 3 C 3 2 C C 3 MW bp 28 C 80 C 8/3/2006 MEDC 501 Fall
16 Consequences of Bond Polarity ydrogen Bonding 2 2 S MW bp 100 C -60 C χ = (6-2)/4 = 1.0 χ S = (6-2)/9 = /3/2006 MEDC 501 Fall S
17 Consequences of Bond Polarity ydrogen Bonding Each in a hydrogen-bond is shared by two e atoms Linear arrangement of three atoms ( plus 2 e) is strongest Each linear arrangement is ~ 4-5 kcal/mol Typically form -bond = -.F- Typically do not form -bond S- - P- = - Cl- 8/3/2006 MEDC 501 Fall
18 Consequences of Bond Polarity ydrogen Bonding - Alcohols C 3 C 2 C 3 C 3 C 2 C 2 MW bp -45 C 78 C.... 8/3/2006 MEDC 501 Fall
19 Consequences of Bond Polarity ydrogen Bonding - Acids C C C MW mp C /3/2006 MEDC 501 Fall
20 Consequences of Bond Polarity ydrogen Bonding - Structure of Proteins and ucleic Acids R1 R9. R2. R10 R3 R11. R4. R12 R5 R13. R6. R14 R7 R15. R8. R16 ydrogen Bonding in β-strands (3D structure) 8/3/2006 MEDC 501 Fall
21 Inductive Effect Consequences of Bond Polarity the transfer of electronegative effect of polar σ bonds to neighboring σ bonds, causing them to be more or less polarized. 8/3/2006 MEDC 501 Fall
22 Consequences of Bond Polarity Change in Acidity or Basicity of Groups C 3 C 3 a carboxylic acid an alcohol C 3 F 3 C a carboxylic acid a trifluoro-carboxylic acid 8/3/2006 MEDC 501 Fall
23 Consequences of Bond Polarity Inductive Effect - Influence on pka 1.25 C 3 3 C pka /3/2006 MEDC 501 Fall
24 Chemical Equilibrium pk A and Ions in Solution k 1 A + B C + D k 2 At equilibrium, k 1 [A] [B] = k 2 [C] [D] k k 1 2 = [ C][ D] [ A][ B] = K E Le Chatelier s Principle: When a stress is applied on a system at equilibrium, the system will re-adjust to diminish the stress or counteract the change. 8/3/2006 MEDC 501 Fall
25 2 Equilibrium pk A and Ions in Solution k 1 + _ 2 + k 2 + [ ][ [ ] 2 ] = K E [ + ][ ] = KE W log[ [ 2] = KE 55.5 = K = 10 + ][ ] = log log[ + ] + log[ ] = 14 + log[ ] log[ ] = 14 p + p =14 8/3/2006 MEDC 501 Fall
26 pk A and Ions in Solution Acidity, basicity and neutrality and p conditions 8/3/2006 MEDC 501 Fall
27 pk A and Ions in Solution Ionization and Strength of Acids and Bases Property of Ionization: The degree of ionization of a particular compound in water is dependent on its structure and is characteristic for that compound. 8/3/2006 MEDC 501 Fall
28 pk A and Ions in Solution Ionization of a weak acid C 3 C C 3 C - K E log pk A = p [ K A K E 2 [ = [ ] = K 3 ][ C3C ] ][ C C ] 2 A = log[ [ C log [ C 3 + [ = ] + ][ C3C [ C C ] 3 [ C log [ C 3 ] C ] C ] C ] [ conj. base] = p log C ] [ acid] 3 [ conj. base] log [ acid] 3 = p pk A enderson-aselbach Equation 8/3/2006 MEDC 501 Fall
29 Consequences of Bond Polarity Inductive Effect - Influence on pka C 3 F 3 C pka C 3 C ClC 2 C pka /3/2006 MEDC 501 Fall
30 Consequences of Bond Polarity Inductive Effect - Additive Property pka C 3 C 4.5 ClC 2 C 2.9 Cl 2 CC 1.3 Cl 3 CC 0.7 8/3/2006 MEDC 501 Fall
31 Consequences of Bond Polarity Inductive Effect - Distance Dependent Property pka C 3 C 2 C 2 C 4.8 ClC 2 C 2 C 2 C 4.5 C 3 CClC 2 C 4.1 C 3 C 2 ClC 2 C 2.8 8/3/2006 MEDC 501 Fall
32 Consequences of Bond Polarity Inductive Effect - Group Electronegativities Electron-withdrawing groups χ -C= = 1.5 -C = 2.5 -C = = 3.0 pka 2 C 2 C 1.7 ClC 2 C 2.9 CC 2 C 2.8 CC 2 C 3.5 8/3/2006 MEDC 501 Fall
33 Consequences of Bond Polarity Inductive Effect Multiple pk A values A molecule may have more than one pk A value!! pk A = 2.8 pk A = 5.7 _ + pk A = pk A = _ 3 _ 2 8/3/2006 MEDC 501 Fall
34 Consequences of Bond Polarity Influence on pka. through space effect Cl Cl C Cl Cl C pka /3/2006 MEDC 501 Fall
35 Consequences of Bond Polarity atural Amino Acids Structure and pk A R C 2 Structure of Amino Acid Residues All L-configuration or R geometry (except for glycine) on-polar R = -Bonding R = Glycine Serine C 2 Alanine C 3 Threonine C 3 C() Valine (C 3 ) 2 C Cysteine SC 2 Leucine (C 3 ) 2 C 2 C Tyrosine C 6 4 C 2 Isoleucine C 3 C 2 C(C 3 ) Asparagine 2 C()C 2 Phenyalanine PhC 2 Glutamine 2 C()C 2 C 2 Methionine 3 CSC 2 C 2 Tryptophan C 2 8/3/2006 MEDC 501 Fall
36 Consequences of Bond Polarity atural Amino Acids Structure and pk A R C 2 Structure of Amino Acid Residues All L-configuration or R geometry (except for glycine) Acidic R = Basic R = Aspartic Acid CC 2 Lysine 2 (C 2 ) 4 Glutamic Acid CC 2 C 2 Arginine 2 C()(C 2 ) 3 istidine 2 C 8/3/2006 MEDC 501 Fall
37 Consequences of Bond Polarity Residues pk A 1 pk A Side-Chain pk A (group identification) on-polar Glycine Alanine Valine Leucine Isoleucine Phenyalanine Methionine Tryptophan ydrogen-bonding Serine Threonine Cysteine (thiol group) Tyrosine (phenol group) Asparagine Glutamine Acidic Aspartic Acid (γ-c group) Glutamic Acid (γ-c group) Basic Lysine (ε-amino group) Arginine (guanidino group) istidine (imidazole group) 8/3/2006 MEDC 501 Fall
38 pka and bases Consequences of Bond Polarity R R 2 pk A = p - log [R 2 ] [R 3+ ] Rank the following amines according to their pk A values. Use 1 for lowest pk A and 3 for highest. C 3 C 2 2 FC 2 C 2 2 C 3 FC 2 Rank the above amines according to their basicity. Use 1 for least basic and 3 for most basic. 8/3/2006 MEDC 501 Fall
39 Inductive Effect Consequences of Bond Polarity depend on the ew atom or e atom is distance dependent may be re-inforced or cancelled is additive can affect the acidity or basicity of molecules can affect the physical properties of molecules 8/3/2006 MEDC 501 Fall
40 Resonance Effect Consequences of Bond Polarity 2 2 pk A /3/2006 MEDC 501 Fall
41 Consequences of Bond Polarity Resonance Effect C C C 2 Me pka _ _ Me Me 8/3/2006 MEDC 501 Fall
42 Resonance Effect Consequences of Bond Polarity Electron-donating groups., Me,, 2, C 3, Cl, F, Br, I Electron-withdrawing groups. 2, C, C, C, S 3, S 2 2, S 2 Cl 8/3/2006 MEDC 501 Fall
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