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Title: A mononuclear nonheme {FeNO} 6 complex: synthesis and structural and spectroscopic characterization

Abstract

While the synthesis and characterization of {FeNO} 7,8,9 complexes have been well documented in heme and nonheme iron models, {FeNO} 6 complexes have been less clearly understood. Herein, we report the synthesis and structural and spectroscopic characterization of mononuclear nonheme {FeNO} 6 and iron(III)–nitrito complexes bearing a tetraamido macrocyclic ligand (TAML), such as [(TAML)Fe III(NO)] - and [(TAML)Fe III(NO 2)] 2-, respectively. First, direct addition of NO (g) to [Fe III(TAML)] - results in the formation of [(TAML)Fe III(NO)] -, which is sensitive to moisture and air. The spectroscopic data of [(TAML)Fe III(NO)] -, such as 1H nuclear magnetic resonance and X-ray absorption spectroscopies, combined with computational study suggest the neutral nature of nitric oxide with a diamagnetic Fe center (S = 0). We also provide alternative pathways for the generation of [(TAML)Fe III(NO)] -, such as the iron–nitrite reduction triggered by protonation in the presence of ferrocene, which acts as an electron donor, and the photochemical iron–nitrite reduction. To the best of our knowledge, the present study reports the first photochemical nitrite reduction in nonheme iron models.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3];  [2];  [3]; ORCiD logo [3];  [3]; ORCiD logo [4];  [5];  [6]; ORCiD logo [7]; ORCiD logo [6]; ORCiD logo [8]
  1. Ewha Womans Univ., Seoul (Korea, Republic of). Dept. of Chemistry and Nano Science; Sookmyung Women's Univ., Seoul (Korea, Republic of). Dept. of Chemistry
  2. Stanford Univ., CA (United States). Dept. of Chemistry
  3. Ewha Womans Univ., Seoul (Korea, Republic of). Dept. of Chemistry and Nano Science
  4. Univ. of California, Santa Cruz, CA (United States). Dept. of Chemistry and Biochemistry
  5. SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource
  6. Stanford Univ., CA (United States). Dept. of Chemistry; SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource
  7. Johns Hopkins Univ., Baltimore, MD (United States). Dept. of Chemistry
  8. Ewha Womans Univ., Seoul (Korea, Republic of). Dept. of Chemistry and Nano Science; Shaanxi Normal Univ., Xi'an (China). School of Chemistry and Chemical Engineering
Publication Date:
Research Org.:
SLAC National Accelerator Lab., Menlo Park, CA (United States); Stanford Univ., CA (United States); Johns Hopkins Univ., Baltimore, MD (United States); Ewha Womans Univ., Seoul (Korea, Republic of)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23); National Inst. of Health (NIH) (United States); National Research Foundation of Korea (NRF)
OSTI Identifier:
1475536
Grant/Contract Number:  
AC02-76SF00515; GM-28962; GM-40392; P41GM103393; NRF-2012R1A3A2048842; NRF-2010-00353; NRF-2017R1C1B2002037
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 9; Journal Issue: 34; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Hong, Seungwoo, Yan, James J., Karmalkar, Deepika G., Sutherlin, Kyle D., Kim, Jin, Lee, Yong-Min, Goo, Yire, Mascharak, Pradip K., Hedman, Britt, Hodgson, Keith O., Karlin, Kenneth D., Solomon, Edward I., and Nam, Wonwoo. A mononuclear nonheme {FeNO}6 complex: synthesis and structural and spectroscopic characterization. United States: N. p., 2018. Web. doi:10.1039/c8sc01962b.
Hong, Seungwoo, Yan, James J., Karmalkar, Deepika G., Sutherlin, Kyle D., Kim, Jin, Lee, Yong-Min, Goo, Yire, Mascharak, Pradip K., Hedman, Britt, Hodgson, Keith O., Karlin, Kenneth D., Solomon, Edward I., & Nam, Wonwoo. A mononuclear nonheme {FeNO}6 complex: synthesis and structural and spectroscopic characterization. United States. doi:10.1039/c8sc01962b.
Hong, Seungwoo, Yan, James J., Karmalkar, Deepika G., Sutherlin, Kyle D., Kim, Jin, Lee, Yong-Min, Goo, Yire, Mascharak, Pradip K., Hedman, Britt, Hodgson, Keith O., Karlin, Kenneth D., Solomon, Edward I., and Nam, Wonwoo. Fri . "A mononuclear nonheme {FeNO}6 complex: synthesis and structural and spectroscopic characterization". United States. doi:10.1039/c8sc01962b. https://www.osti.gov/servlets/purl/1475536.
@article{osti_1475536,
title = {A mononuclear nonheme {FeNO}6 complex: synthesis and structural and spectroscopic characterization},
author = {Hong, Seungwoo and Yan, James J. and Karmalkar, Deepika G. and Sutherlin, Kyle D. and Kim, Jin and Lee, Yong-Min and Goo, Yire and Mascharak, Pradip K. and Hedman, Britt and Hodgson, Keith O. and Karlin, Kenneth D. and Solomon, Edward I. and Nam, Wonwoo},
abstractNote = {While the synthesis and characterization of {FeNO}7,8,9 complexes have been well documented in heme and nonheme iron models, {FeNO}6 complexes have been less clearly understood. Herein, we report the synthesis and structural and spectroscopic characterization of mononuclear nonheme {FeNO}6 and iron(III)–nitrito complexes bearing a tetraamido macrocyclic ligand (TAML), such as [(TAML)FeIII(NO)]- and [(TAML)FeIII(NO2)]2-, respectively. First, direct addition of NO(g) to [FeIII(TAML)]- results in the formation of [(TAML)FeIII(NO)]-, which is sensitive to moisture and air. The spectroscopic data of [(TAML)FeIII(NO)]-, such as 1H nuclear magnetic resonance and X-ray absorption spectroscopies, combined with computational study suggest the neutral nature of nitric oxide with a diamagnetic Fe center (S = 0). We also provide alternative pathways for the generation of [(TAML)FeIII(NO)]-, such as the iron–nitrite reduction triggered by protonation in the presence of ferrocene, which acts as an electron donor, and the photochemical iron–nitrite reduction. To the best of our knowledge, the present study reports the first photochemical nitrite reduction in nonheme iron models.},
doi = {10.1039/c8sc01962b},
journal = {Chemical Science},
number = 34,
volume = 9,
place = {United States},
year = {2018},
month = {7}
}

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    Works referencing / citing this record:

    Characterization of a High-Spin Non-Heme {FeNO} 8 Complex: Implications for the Reactivity of Iron Nitroxyl Species in Biology
    journal, October 2013

    • Speelman, Amy L.; Lehnert, Nicolai
    • Angewandte Chemie International Edition, Vol. 52, Issue 47
    • DOI: 10.1002/anie.201305291

    Structural and Spectroscopic Characterization of a High-Spin {FeNO} 6 Complex with an Iron(IV)−NO Electronic Structure
    journal, April 2016

    • Speelman, Amy L.; Zhang, Bo; Krebs, Carsten
    • Angewandte Chemie International Edition, Vol. 55, Issue 23
    • DOI: 10.1002/anie.201601742

    Peroxynitrite, a potent macrophage-derived oxidizing cytotoxin to combat invading pathogens: Peroxynitrite in Pathogen Invasion
    journal, November 2013

    • Prolo, Carolina; Álvarez, María Noel; Radi, Rafael
    • BioFactors, Vol. 40, Issue 2
    • DOI: 10.1002/biof.1150

    Evaluation of the Magnitude and Rate of Nitric Oxide Production from Nitrite in Biological Systems
    journal, September 1998

    • Samouilov, Alexandre; Kuppusamy, Periannan; Zweier, Jay L.
    • Archives of Biochemistry and Biophysics, Vol. 357, Issue 1
    • DOI: 10.1006/abbi.1998.0785

    Spreadsheet based analysis of Mössbauer spectra
    journal, March 2016


    A 13-element Ge detector for fluorescence EXAFS
    journal, April 1988

    • Cramer, S. P.; Tench, O.; Yocum, M.
    • Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment, Vol. 266, Issue 1-3
    • DOI: 10.1016/0168-9002(88)90449-4

    The role of nitrite ion in phagocyte function—perspectives and puzzles
    journal, April 2009

    • Cape, Jonathan L.; Hurst, James K.
    • Archives of Biochemistry and Biophysics, Vol. 484, Issue 2
    • DOI: 10.1016/j.abb.2009.01.010

    Model complexes of key intermediates in fungal cytochrome P450 nitric oxide reductase (P450nor)
    journal, April 2014

    • McQuarters, Ashley B.; Wirgau, Nathaniel E.; Lehnert, Nicolai
    • Current Opinion in Chemical Biology, Vol. 19
    • DOI: 10.1016/j.cbpa.2014.01.017

    Generation, Translocation, and Action of Nitric Oxide in Living Systems
    journal, October 2011


    Mitochondrial cytochrome oxidase produces nitric oxide under hypoxic conditions: Implications for oxygen sensing and hypoxic signaling in eukaryotes
    journal, April 2006


    Nitric oxide reductase (P450) from
    journal, January 2005


    Nitric oxide reductases of prokaryotes with emphasis on the respiratory, heme?copper oxidase type
    journal, January 2005


    Crystal structures of the nitrite and nitric oxide complexes of horse heart myoglobin
    journal, August 2006


    Weak coordination of neutral S- and O-donor proximal ligands to a ferrous porphyrin nitrosyl. Characterization of 6-coordinate complexes at low T
    journal, April 2013


    Heme-Nitrosyls: Electronic Structure Implications for Function in Biology
    journal, June 2015


    Six-Coordinate Ferrous Nitrosyl Complex Fe II (TTP)(PMe 3 )(NO) (TTP = meso -Tetra- p -tolylporphyrinato Dianion)
    journal, September 2016


    Ferric Heme-Nitrosyl Complexes: Kinetically Robust or Unstable Intermediates?
    journal, August 2017


    TAML Oxidant Activators:  A New Approach to the Activation of Hydrogen Peroxide for Environmentally Significant Problems
    journal, September 2002

    • Collins, Terrence J.
    • Accounts of Chemical Research, Vol. 35, Issue 9
    • DOI: 10.1021/ar010079s

    Mechanistic Aspects of the Reactions of Nitric Oxide with Transition-Metal Complexes
    journal, April 2002

    • Ford, Peter C.; Lorkovic, Ivan M.
    • Chemical Reviews, Vol. 102, Issue 4
    • DOI: 10.1021/cr0000271

    Paramagnetic moment measurements by nmr. A micro technique
    journal, September 1972

    • Loliger, J.; Scheffold, R.
    • Journal of Chemical Education, Vol. 49, Issue 9
    • DOI: 10.1021/ed049p646

    Photochemical reduction of nitrate and nitrite by manganese and iron porphyrins
    journal, March 1991

    • Suslick, Kenneth S.; Watson, Randall A.
    • Inorganic Chemistry, Vol. 30, Issue 5
    • DOI: 10.1021/ic00005a009

    Iron Nitrosyls of a Pentadentate Ligand Containing a Single Carboxamide Group:  Syntheses, Structures, Electronic Properties, and Photolability of NO
    journal, October 2003

    • Patra, Apurba K.; Rowland, John M.; Marlin, Dana S.
    • Inorganic Chemistry, Vol. 42, Issue 21
    • DOI: 10.1021/ic0301627

    (TAML)Fe IV O Complex in Aqueous Solution: Synthesis and Spectroscopic and Computational Characterization
    journal, May 2008

    • Chanda, Arani; Shan, Xiaopeng; Chakrabarti, Mrinmoy
    • Inorganic Chemistry, Vol. 47, Issue 9
    • DOI: 10.1021/ic7022902

    Calibration of Modern Density Functional Theory Methods for the Prediction of 57 Fe Mössbauer Isomer Shifts: Meta-GGA and Double-Hybrid Functionals
    journal, February 2009

    • Römelt, Michael; Ye, Shengfa; Neese, Frank
    • Inorganic Chemistry, Vol. 48, Issue 3
    • DOI: 10.1021/ic801535v

    X-ray absorption, Moessbauer, and EPR studies of the dinuclear iron center in the hydroxylase component of methane monooxygenase
    journal, November 1991

    • DeWitt, Jane G.; Bentsen, James G.; Rosenzweig, Amy C.
    • Journal of the American Chemical Society, Vol. 113, Issue 24
    • DOI: 10.1021/ja00024a031

    Polarized x-ray absorption spectra of oriented plastocyanin single crystals. Investigation of methionine-copper coordination
    journal, October 1982

    • Scott, Robert A.; Hahn, James E.; Doniach, Sebastian
    • Journal of the American Chemical Society, Vol. 104, Issue 20
    • DOI: 10.1021/ja00384a020

    A systematic x-ray absorption study of molybdenum complexes. The accuracy of structural information from extended x-ray absorption fine structure
    journal, April 1978

    • Cramer, Stephen P.; Hodgson, Keith O.; Stiefel, Edward I.
    • Journal of the American Chemical Society, Vol. 100, Issue 9
    • DOI: 10.1021/ja00477a030

    Nonheme Fe IV O Complexes That Can Oxidize the C−H Bonds of Cyclohexane at Room Temperature
    journal, January 2004

    • Kaizer, József; Klinker, Eric J.; Oh, Na Young
    • Journal of the American Chemical Society, Vol. 126, Issue 2
    • DOI: 10.1021/ja037288n

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