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Organic nitroxyls such as 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) are stable in solution and widely used as catalysts and mediators in chemical and electrochemical redox reactions, such as alcohol oxidation. The three most common species involved in these reactions are illustrated in the figure below. Hydroxylam- monium (RNOH, not shown), the conjugate acid of hydroxylamine (RNOH), is the 4th species involved. OH 2,6,6-tetramethylpiperidine-N-oxyl (TEMPO, noted RNO) Data:: pKa (RNOH/RNOH) = 7.34; E° (RNO+/RNO) = 0.74/SHE ; E (RNO/RNOH) = 0.64 V/SHE The following incomplete diagram¹ is plotted for the 4 species above, all at a concentration of 0.01 mol.L-¹. Hydroxylamine (RNOH) I Oxoammonium (RNO*)

Organic nitroxyls such as 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) are stable in solution and widely used as catalysts and mediators in chemical and electrochemical redox reactions, such as alcohol oxidation. The three most common species involved in these reactions are illustrated in the figure below. Hydroxylam- monium (RNOH, not shown), the conjugate acid of hydroxylamine (RNOH), is the 4th species involved. OH 2,6,6-tetramethylpiperidine-N-oxyl (TEMPO, noted RNO) Data:: pKa (RNOH/RNOH) = 7.34; E° (RNO+/RNO) = 0.74/SHE ; E (RNO/RNOH) = 0.64 V/SHE The following incomplete diagram¹ is plotted for the 4 species above, all at a concentration of 0.01 mol.L-¹. Hydroxylamine (RNOH) I Oxoammonium (RNO*)

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Organic nitroxyls such as 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) are stable in solution and widely used as catalysts and mediators in chemical and electrochemical redox reactions, such as alcohol oxidation. The three most common species involved in these reactions are illustrated in the figure below. Hydroxylam- monium (RNOH, not shown), the conjugate acid of hydroxylamine (RNOH), is the 4th species involved. E/SHE(V) 2,6,6-tetramethylpiperidine-N-oxyl (TEMPO, noted RNO) Data: pKa (RNOH/RNOH) 7.34; E = (RNO+/RNO) 0.74/SHE; E° (RNO/RNOH) The following incomplete diagram¹ is plotted for the 4 species above, all at a concentration of 0.01 mol.L-¹. Hydroxylamine (RNOH) 0.5 OH 0 0 4 III 2 I 6 7.34 8 pH @ IV 1 10 Oxoammonium (RNO+) II 12 0.64 V/SHE 14 1. For each species, RNOH, RNOH, RNO and RNO+, calculate the formal oxidation number of nitrogen. The oxidation number of the R. moiety is always +II. 2. For each domain I, II, III and IV of the diagram, which species is prevalent? Explain briefly.( 3. Write the chemical equations corresponding to lines 1 to 4. 4. Determine the expressions of the corresponding potentials E₁ to E4 in function of pH. 5. Calculate the pH value below which TEMPO is not stable, name the reaction and write its chemical equa- tion.
Transcribed Image Text:Organic nitroxyls such as 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) are stable in solution and widely used as catalysts and mediators in chemical and electrochemical redox reactions, such as alcohol oxidation. The three most common species involved in these reactions are illustrated in the figure below. Hydroxylam- monium (RNOH, not shown), the conjugate acid of hydroxylamine (RNOH), is the 4th species involved. E/SHE(V) 2,6,6-tetramethylpiperidine-N-oxyl (TEMPO, noted RNO) Data: pKa (RNOH/RNOH) 7.34; E = (RNO+/RNO) 0.74/SHE; E° (RNO/RNOH) The following incomplete diagram¹ is plotted for the 4 species above, all at a concentration of 0.01 mol.L-¹. Hydroxylamine (RNOH) 0.5 OH 0 0 4 III 2 I 6 7.34 8 pH @ IV 1 10 Oxoammonium (RNO+) II 12 0.64 V/SHE 14 1. For each species, RNOH, RNOH, RNO and RNO+, calculate the formal oxidation number of nitrogen. The oxidation number of the R. moiety is always +II. 2. For each domain I, II, III and IV of the diagram, which species is prevalent? Explain briefly.( 3. Write the chemical equations corresponding to lines 1 to 4. 4. Determine the expressions of the corresponding potentials E₁ to E4 in function of pH. 5. Calculate the pH value below which TEMPO is not stable, name the reaction and write its chemical equa- tion.
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