Nucleophilic Substitutions. Ionic liquids
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1 ucleophilic Substitutions & Ionic liquids
2 S 2 Reaction S 2 Substitution Reaction ucleophilic (electron rich) Bimolecular The rate depends on the concentration of both of the reactants
3 S 2 Reaction Mechanism Leaving group OH H 3 C I H H δ - δ + δ - HO I H CH 3 OH Transition State nucleophile electrophile
4 S 2 Reaction Transition State OH H b H a H c I H a δ - H δ - HO b I H c δ + The partial negative charges are as far apart as possible Backside attack of the nucleophile HO H b H c H a I - Product has inverted stereochemistry
5 S 1 Reaction S 1 Substitution Reaction Unimolecular or 1st order ucleophilic (electron rich) The rate depends only on the concentration of reactant and not on the nucleophile
6 S 1 Reaction - Mechanism I ionization slow I u fast u I (+) or (-) or ( ) ( )
7 H H C H H C H H C H H H CH 3 + CH 3 CH 2 + (CH 3 ) 2 CH + (CH 3 ) 3 C + Increasing carboca4on stability - increasing S 1 rate
8 Rearrangement occurs if an alkyl group, aryl group or hydrogen shift would lead to a more stable cation A methide shi@ CH 3 CH 3 H 3 C C CHCH 2 CH 3 H 3 C C CHCH 2 CH 3 CH 3 CH 3 2 o 3 o A hydride shi@ H 3 C H C CHCH 2 CH 3 H 3 C C CH 3 CH 3 CCH 2 CH 3 2 o 3 o
9 Pinacol-Pinacolone Rearrangement HO Ph Ph OH Ph Ph H HO Ph Ph OH 2 Ph Ph H 2 O HO Ph Ph Ph Ph O Ph H O Ph HO Ph Ph Ph Ph Ph Ph Ph Ph Ph Ph
10 Allylic chloride in S 1 reac4on Cl Cl - CH 2 H 2 C Resonance structures - structures differing only in the posi4on of π electrons
11 Allylic chloride in S 2 reac4on OH - OH - OH Cl Cl -
12 For increased stabiliza4on to occur either in S 1 or S 2 reac4ons, the π system MUST be adjacent to the reac4ng carbon Br Cl Br Cl
13 ucleophilicity vs Basicity u vs B Substitution vs Elimination S vs E
14 CHARGE DESITY 1. Size of the negative charge 2. Size of the groups around the negative charge 3. Accessibility of the positive charge 4. Solvent interactions 5. Counter ion interactions
15 REACTIO EFFICIECY GREE CHEMISTRY IOIC LIQUIDS
16 Calculation of atom economy Atom economy mass of atoms in desired product mass of atoms in reactants X 100%
17 O 4 1/2 O 2 O 2CO 2 2H 2 O MW 78 MW 144 MW 96 O atom economy 96 (desired product) (reactants) X 100% 43%
18 Reactions can give quantitative yields, but can be very atom inefficient Reaction can be give 100% atom economy, but not quantitative yield O OH heat
19 Click Chemistry Following nature's lead, we endeavor to generate substances by joining small units together with heteroatom links (C-X-C). The goal is to develop an expanding set of powerful, selective, and modular blocks that work reliably in both small- and large-scale applications. The reaction must be modular, wide in scope, give very high yields, generate only inoffensive byproducts that can be removed by nonchromatographic methods, and be stereospecific K. Barry Sharpless, 2001
20 The required process characteristics: Simple reaction conditions (ideally, the process should be insensitive to oxygen and water) Readily available starting materials and reagents The use of no solvent or a solvent that is benign (such as water) or easily removed Purification - crystallization or distillation The product must be stable under physiological conditions.
21 Sharpless, Finn, Kolb, 2001
22 Ionic Liquids Green or Designer Solvents
23 Applications of Ionic Liquids
24 Evolution of ionic liquids Classification Description Examples (m.p.) Molten salts inorganic salts in a liquid-like state acl (801 o C) acl-alcl 3 50/50 (151 o C) Ionic liquids salts composed of an organic cation and an inorganic / organic anion or an inorganic cation and a polyoxometalate anion Cl (70 o C) Roomtemperature ionic liquids ionic liquids that possess phase transitions at or below room temperature H 3 O 3 (5 o C) K. R. Seddon, J. Chem. Tech. Biotech. 1997, 68, 351. J. S. Wilkes, Green Chem., 2002, 4, 73.
25 Room-Temperature Ionic Liquids Are Green(er) Alternatives to Volatile, Hazardous, asty Molecular Solvents Molecular Organic Solvents Volatile Low thermal stability Difficult to recycle Limited structural variations Inexpensive Ionic Liquids on-volatile High thermal stability Easy to recycle and reuse Endless structural variations Expensive ACS Symposium Series 818, 2002; ACS Symposium Series 856, 2003
26 Ionic Liquids R R 1 P R R A R A 1 A R imidazolium pyridinium phosphonium R R 1 A ammonium R R R R A guanidinium R 1 A R pyrrolidinium
27 Imidazolium-based ionic liquids H R 1 R R 2 1 imidazole alkyl imidazole dialkyl imidazolium ah R 2 R 1 Br Br R 1 R 1 and R 2 = H, alkyl, aralkyl, allyl, etc.
28 C 4 H 9 X conditions X Conditions MR yield, % X = Cl, 70 o C, 48h 95 X = Br, 70 o C, 2h 99 X = Br, 110 o C, 1h 100 X = Br, 140 o C, 0.5h 100 J. Heterocyclic Chem. 2001, 38, 265.
29 Imidazolium BROMIDES (or halides) R Br R' apple apple apple Hygroscopic Solids or oils ot quite thermally stable
30 Metathesis Reactions Br C n H 2n+1 [C n -mim]br HPF 6 or KPF 6 H 2 O, r.t., 30 min PF 6 C n H 2n+1 [C n -mim]pf % Br n Li(SO 2 CF 3 ) 2 [LiTf 2 ] H 2 O, r.t., 30 min Tf 2 n % [PhCH 2 -mim]br [PhCH 2 -mim]tf 2
31 Designer Solvent Interplay STRUCTURE identity of anion and cation
32 Exotic, Task-Specific and House-Hold Ionic Liquids Cl Cl Cl O 1) RI, heat 2) apf 6 Cl Cl Cl O PF 6 R Miconazole (antifungal drug) Cl R = CH 3, C 2 H 3, C 3 H 7, (CH 2 ) 2 (CF 2 ) 5 CF 3 Cl JH Davis Jr, KJ Forrester, T Merrigan, Tetrahedron Lett., 1998, 39, 8955 O PF 6 O Cl Cl Ru PCy 3 H Q. Yao, Y. Zhang, Angew. Chem. Int. Ed. 2003, 42, 3395 EB Carter et al., Chem. Commun. 2004, 630
33 aturally-occurring Ionic Liquids X OH X = Cl, CF 3 COO, etc. Fishkin, Y-P Jang, Y Itagaki, JR Sparrow, K akanishi, Org. Biomol. Chem. 2003, 1, 1101.
34 DESIGER SOLVETS It is possible to design a solvent to optimize a reaction with control over both yield and selectivity (rather than to let the solvent dictate the course of the reaction) by fine-tuning such phenomena as the relative solubilities of the reactants and products, the reaction kinetics, the liquid range of the solvent, the cost of the solvent, the intrinsic behavior of the media, and the air stability of the system. K. R. Seddon M. Freemantle, Chem. Eng. ews, 1998, March 30, 32
35 Designer Solvent Interplay STRUCTURE identity of anion and cation PROPERTY phase transitions density, polarity
36 Phase transitions - measured by Differential Scanning Calorimetry PF 6 C n H 2n+1 50 T, o C n [C n -mim]pf 6
![Densities of Room-Temperature Ionic Liquids X 1.5 [C n -mim]pf 6 Cn H 2n+1 d, g/ml 1.](/docs-images/89/98919039/images/37-2.jpg "4 [C n -mim]tf 2 X = PF 6, (SO 2 CF 3 ) 2 1.3 1.")
37 Densities of Room-Temperature Ionic Liquids X 1.5 [C n -mim]pf 6 Cn H 2n+1 d, g/ml 1.4 [C n -mim]tf 2 X = PF 6, (SO 2 CF 3 ) n ChemPhysChem, 2002, 3, 161.
38 Viscosity of Room-Temperature Ionic Liquids [C 4 -mim]pf 6 η / cp 500 η / cp [C n -mim]pf T / oc n X Cn H 2n+1 ChemPhysChem, 2002, 3, 161.
39 Designer Solvent Interplay STRUCTURE identity of anion and cation PROPERTY phase transitions density, polarity FUCTIO efficiency, selectivity diversity
40 Confirming designer solvent paradigm CH 3 OSO 2 CF 3 HO 3 Cl CH 3 OSO 2 CH 3 CH 3 O 2 COOH Cl M. J. Earle, S. P. Katdare, K. R. Seddon, Org. Lett., 2004, 6, 707
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