Enhanced Redox Reactivity of a Nonheme Iron(V)–Oxo Complex Binding Proton
Acid effects on the chemical properties of metal–oxygen intermediates have attracted much attention recently, such as the enhanced reactivity of high-valent metal(IV)–oxo species by binding proton(s) or Lewis acidic metal ion(s) in redox reactions. Herein, we report for the first time the proton ef...
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Published in | Journal of the American Chemical Society Vol. 142; no. 36; pp. 15305 - 15319 |
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Main Authors | , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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United States
American Chemical Society
09.09.2020
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Abstract | Acid effects on the chemical properties of metal–oxygen intermediates have attracted much attention recently, such as the enhanced reactivity of high-valent metal(IV)–oxo species by binding proton(s) or Lewis acidic metal ion(s) in redox reactions. Herein, we report for the first time the proton effects of an iron(V)–oxo complex bearing a negatively charged tetraamido macrocyclic ligand (TAML) in oxygen atom transfer (OAT) and electron-transfer (ET) reactions. First, we synthesized and characterized a mononuclear nonheme Fe(V)–oxo TAML complex (1) and its protonated iron(V)–oxo complexes binding two and three protons, which are denoted as 2 and 3, respectively. The protons were found to bind to the TAML ligand of the Fe(V)–oxo species based on spectroscopic characterization, such as resonance Raman, extended X-ray absorption fine structure (EXAFS), and electron paramagnetic resonance (EPR) measurements, along with density functional theory (DFT) calculations. The two-protons binding constant of 1 to produce 2 and the third protonation constant of 2 to produce 3 were determined to be 8.0(7) × 108 M–2 and 10(1) M–1, respectively. The reactivities of the proton-bound iron(V)–oxo complexes were investigated in OAT and ET reactions, showing a dramatic increase in the rate of sulfoxidation of thioanisole derivatives, such as 107 times increase in reactivity when the oxidation of p-CN-thioanisole by 1 was performed in the presence of HOTf (i.e., 200 mM). The one-electron reduction potential of 2 (E red vs SCE = 0.97 V) was significantly shifted to the positive direction, compared to that of 1 (E red vs SCE = 0.33 V). Upon further addition of a proton to a solution of 2, a more positive shift of the E red value was observed with a slope of 47 mV/log([HOTf]). The sulfoxidation of thioanisole derivatives by 2 was shown to proceed via ET from thioanisoles to 2 or direct OAT from 2 to thioanisoles, depending on the ET driving force. |
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AbstractList | Acid effects on the chemical properties of metal–oxygen intermediates have attracted much attention recently, such as the enhanced reactivity of high-valent metal(IV)–oxo species by binding proton(s) or Lewis acidic metal ion(s) in redox reactions. Herein, we report for the first time the proton effects of an iron(V)–oxo complex bearing a negatively charged tetraamido macrocyclic ligand (TAML) in oxygen atom transfer (OAT) and electron-transfer (ET) reactions. First, we synthesized and characterized a mononuclear nonheme Fe(V)–oxo TAML complex (1) and its protonated iron(V)–oxo complexes binding two and three protons, which are denoted as 2 and 3, respectively. The protons were found to bind to the TAML ligand of the Fe(V)–oxo species based on spectroscopic characterization, such as resonance Raman, extended X-ray absorption fine structure (EXAFS), and electron paramagnetic resonance (EPR) measurements, along with density functional theory (DFT) calculations. The two-protons binding constant of 1 to produce 2 and the third protonation constant of 2 to produce 3 were determined to be 8.0(7) × 108 M–2 and 10(1) M–1, respectively. The reactivities of the proton-bound iron(V)–oxo complexes were investigated in OAT and ET reactions, showing a dramatic increase in the rate of sulfoxidation of thioanisole derivatives, such as 107 times increase in reactivity when the oxidation of p-CN-thioanisole by 1 was performed in the presence of HOTf (i.e., 200 mM). The one-electron reduction potential of 2 (E red vs SCE = 0.97 V) was significantly shifted to the positive direction, compared to that of 1 (E red vs SCE = 0.33 V). Upon further addition of a proton to a solution of 2, a more positive shift of the E red value was observed with a slope of 47 mV/log([HOTf]). The sulfoxidation of thioanisole derivatives by 2 was shown to proceed via ET from thioanisoles to 2 or direct OAT from 2 to thioanisoles, depending on the ET driving force. Acid effects on the chemical properties of metal-oxygen intermediates have attracted much attention recently, such as the enhanced reactivity of high-valent metal(IV)-oxo species by binding proton(s) or Lewis acidic metal ion(s) in redox reactions. Herein, we report for the first time the proton effects of an iron(V)-oxo complex bearing a negatively charged tetraamido macrocyclic ligand (TAML) in oxygen atom transfer (OAT) and electron-transfer (ET) reactions. First, we synthesized and characterized a mononuclear nonheme Fe(V)-oxo TAML complex ( ) and its protonated iron(V)-oxo complexes binding two and three protons, which are denoted as and , respectively. The protons were found to bind to the TAML ligand of the Fe(V)-oxo species based on spectroscopic characterization, such as resonance Raman, extended X-ray absorption fine structure (EXAFS), and electron paramagnetic resonance (EPR) measurements, along with density functional theory (DFT) calculations. The two-protons binding constant of to produce and the third protonation constant of to produce were determined to be 8.0(7) × 10 M and 10(1) M , respectively. The reactivities of the proton-bound iron(V)-oxo complexes were investigated in OAT and ET reactions, showing a dramatic increase in the rate of sulfoxidation of thioanisole derivatives, such as 10 times increase in reactivity when the oxidation of -CN-thioanisole by was performed in the presence of HOTf (i.e., 200 mM). The one-electron reduction potential of ( vs SCE = 0.97 V) was significantly shifted to the positive direction, compared to that of ( vs SCE = 0.33 V). Upon further addition of a proton to a solution of , a more positive shift of the value was observed with a slope of 47 mV/log([HOTf]). The sulfoxidation of thioanisole derivatives by was shown to proceed via ET from thioanisoles to or direct OAT from to thioanisoles, depending on the ET driving force. |
Author | Seo, Mi Sook Sarangi, Ritimukta Kim, Sun Hee Lee, Yong-Min Li, Xiao-Xi Nam, Wonwoo Fukuzumi, Shunichi Kim, Yujeong Jeon, Young-Kyo Yanagisawa, Sachiko Kubo, Minoru Kim, Won-Suk Xue, Shan-Shan |
AuthorAffiliation | Graduate School of Life Science Department of Chemistry and Nano Science Stanford Synchrotron Radiation Lightsource School of Chemistry and Chemical Engineering Western Seoul Center University of Jinan |
AuthorAffiliation_xml | – name: Stanford Synchrotron Radiation Lightsource – name: School of Chemistry and Chemical Engineering – name: University of Jinan – name: Department of Chemistry and Nano Science – name: Western Seoul Center – name: Graduate School of Life Science |
Author_xml | – sequence: 1 givenname: Shan-Shan orcidid: 0000-0001-7093-7825 surname: Xue fullname: Xue, Shan-Shan organization: Department of Chemistry and Nano Science – sequence: 2 givenname: Xiao-Xi orcidid: 0000-0002-3593-7536 surname: Li fullname: Li, Xiao-Xi organization: Department of Chemistry and Nano Science – sequence: 3 givenname: Yong-Min orcidid: 0000-0002-5553-1453 surname: Lee fullname: Lee, Yong-Min organization: Department of Chemistry and Nano Science – sequence: 4 givenname: Mi Sook orcidid: 0000-0003-3302-2508 surname: Seo fullname: Seo, Mi Sook organization: Department of Chemistry and Nano Science – sequence: 5 givenname: Yujeong orcidid: 0000-0001-7667-996X surname: Kim fullname: Kim, Yujeong organization: Western Seoul Center – sequence: 6 givenname: Sachiko surname: Yanagisawa fullname: Yanagisawa, Sachiko organization: Graduate School of Life Science – sequence: 7 givenname: Minoru surname: Kubo fullname: Kubo, Minoru organization: Graduate School of Life Science – sequence: 8 givenname: Young-Kyo surname: Jeon fullname: Jeon, Young-Kyo organization: Department of Chemistry and Nano Science – sequence: 9 givenname: Won-Suk orcidid: 0000-0001-9180-4570 surname: Kim fullname: Kim, Won-Suk organization: Department of Chemistry and Nano Science – sequence: 10 givenname: Ritimukta orcidid: 0000-0002-2764-2279 surname: Sarangi fullname: Sarangi, Ritimukta organization: Stanford Synchrotron Radiation Lightsource – sequence: 11 givenname: Sun Hee orcidid: 0000-0001-6557-1996 surname: Kim fullname: Kim, Sun Hee email: shkim7@kbsi.re.kr organization: Western Seoul Center – sequence: 12 givenname: Shunichi orcidid: 0000-0002-3559-4107 surname: Fukuzumi fullname: Fukuzumi, Shunichi email: fukuzumi@chem.eng.osaka-u.ac.jp organization: Department of Chemistry and Nano Science – sequence: 13 givenname: Wonwoo orcidid: 0000-0001-8592-4867 surname: Nam fullname: Nam, Wonwoo email: wwnam@ewha.ac.kr organization: University of Jinan |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32786748$$D View this record in MEDLINE/PubMed |
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Snippet | Acid effects on the chemical properties of metal–oxygen intermediates have attracted much attention recently, such as the enhanced reactivity of high-valent... Acid effects on the chemical properties of metal-oxygen intermediates have attracted much attention recently, such as the enhanced reactivity of high-valent... |
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SubjectTerms | Density Functional Theory Iron Compounds - chemical synthesis Iron Compounds - chemistry Molecular Conformation Oxidation-Reduction Oxygen - chemistry Protons |
Title | Enhanced Redox Reactivity of a Nonheme Iron(V)–Oxo Complex Binding Proton |
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