Advanced Analytical Chemistry Lecture 19. Chem 4631
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1 Advanced Analytical Chemistry Lecture 19 Chem 4631
2
3 Organic Electrochemistry is a multidisciplinary science overlapping the fields of organic chemistry, biochemistry, physical chemistry and electrochemistry. The first electroorganic synthesis was performed by Michael Faraday (1843), the anodic decarboxylation of acetic acid, and the formation of ethane via creation of a new carboncarbon bond: 2 CH 3 COO CH 3 CH 3 + 2CO 2-2e- Pt
4 Organic electrosynthesis Pharmaceuticals (Chiral products) Agrochemicals (fluorinated compounds) Fine chemicals (free base of cysteine) Organic electrosynthesis Complex natural products (b-hydroxyalkonates) Precursors intermediates
5 Many organic reactions are Lewis acid-base processes that involve the interaction of a nucleophilic center with an electrophilic center. Nucleophile (Lewis base) donates electrons and electrophile (Lewis acid) accepts electrons Electrochemistry provides the electrons needed for these reactions.
6 Electrochemistry provides the electrons needed for these reactions. The cathode acts as the ultimate nucleophile and the anode as the electrophile.
7 Carbon centers (saturated hydrocarbons) are resistant to electrochemical reduction or oxidation. Organic molecules with electrophilic components (alkyl-, aryl-, acyl-halides; carbonyl groups, unsaturated and aromatic hydrocarbons, nitro groups) react with the solvated electron (nucleophile).
8 The reduction potential, E red, is a measure of the molecules electron affinity. EP + e- EP- E red More positive the potential the more electrophilic the molecule.
9 Organic molecules with nucleophilic components (catechols, hydroquinones, phenols, alcohols, thiols, aromatic hydrocarbons, and amines) can be oxidized. NP: - e- Nu+ E ox The more negative the potential the more nucleophilic the molecule.
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11 Example of electrophilic reaction (halo-groups)
12 Example of nucleophilic reaction (ring can delocalize the charge).
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14 Non-aqueous Solvents Solvents other than water are generally organic solvents (although recently ionic liquids have been introduced).
15 Non-aqueous Solvents Properties to consider: Boiling point Toxicity Viscosity (influences rate of mass transfer) Relative permittivity, e r (influences electrostatic interactions between electric charges) e r >15 are polar Acidity (ability to accept electrons and donate protons) Basicity (ability to donate electrons and accept protons)
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17 DN basicity scale AN acidity scale
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19 Non-aqueous Solvents Potential window (electrochemical window) are convenient to predict the usefulness of solvents for redox reactions.
20 Non-aqueous Solvents
21 Since there is no reliable reference electrode for non-aqueous solutions, IUPAC has developed a method for reporting electrode potentials.
22 IUPAC method Ferrocene Fc + /Fc or bis(biphenyl)chromium BCr + /BCr are used as reference redox system. Potential of the reference redox system cannot overlap with the system under study. A quasi (typically Pt) or designed reference is used as a reference electrode. System under study is run first then reference redox system is added which cannot affect potential of test redox.
23 Non-aqueous Solvents
24 The potentials of Fc + /Fc and BCr + /BCr couples are almost solvent-independent, making comparison of potentials easy
25 Non-aqueous Solvents
26 The cell for organic reactions is a regular three electrode cell. Working electrode can be Pt, Au, GC, boron-doped diamond with a Pt wire quasi-reference situated close to the WE. The electroactive species must dissolve in the solvent, A polar solvent of weak acidity is suitable for reactions at negative potentials (DMF, DMSO) A polar solvent of weak basicity is suitable for reactions at positive potentials (AN)
27 Non-Aqueous Electrolytes CH 3 CN, DMF, DMSO, THF, Methylene chloride and Ethanol (distillation + storage over 3Å molecular sieves. Storage over activated carbon also)
28 The supporting electrolyte is often Tetraalkylammonium salts Tetrafluoroborates, hexafluorophosphates, and trifluoromethanesulfonates (R 4 NBF 4, R 4 NPF 6, R 4 NOSO 2 CF 3 ) are most popular. Tetrabutylammonium hexafluorophosphate (Bu 4 NPF 6 ) Tetrabutylammonium tetrafluoroborate (Bu 4 NBF 4 ) LiClO 4 Still must be ultrapure.
29 Supporting electrolytes needs to be Soluble in the solvent Dissociate into ions for conductivity Resistant to oxidation and reduction (wide potential window) Does not react with analyte Available in reasonable purity and cost Not toxic or dangerous
30
31 Organometallic complexes are best studied in organic solutions since most are insoluble in aqueous solutions. Example: cobalticinium
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33 Porphyrins and Metalloporphyrins Class of cyclic compounds in which the parent macrocycle consists of four pyrrole-type units linked together by single carbon bridges which carry out vital biochemical processes in living organisms.
34 Metalloporphyrins can have up to three electroactive sites: Metal-free porphyrin can form radical anion and dianion and can form radical cation and dication Metal center can be oxidized and reduced Axial ligands can be electroactive
35
36 CV established that each porphyrin underwent two reversible one-electron oxidations at 492 and 725 mv (vs Fc/Fc + (ferrocene reference)) for the freebase porphyrin and at 329 and 589 mv (vs Fc/Fc + ) for the Znmetalloporphyrin. Electron-transfer rates were also determined to fall between and cm s 1.
37 Reduction of organic compounds Outer sphere type Dissociation type Outer sphere reductions usually are a oneelectron process producing a radical anion, Q - Q + e - Q -
38 Q -, is generally reactive, but its lifetime varies depending on the environment. Aprotic solvents, i.e. tetraalkylammonium salts, help stabilize the radical, and study using CV.
39
40 Outer sphere type Example: Buckminsterfullerene (C 60 ) in AN/toluene at -10 o C Has six one-electron reversible steps in CV, can accept up to six 6 electrons to form diamagnetic, C 60, because its LUMO is triply degenerate.
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42 Test 3 Due today
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