Vibrational properties of heme-nitrosoalkane complexes in comparison with those of their HNO analogs, and reactivity studies towards nitric oxide and Lewis acids

Harland, Jill B.; LaLonde, Ashley B.; Thomas, Diamond J.; Castella, Daniel G.; Kampf, Jeff W.; Zeller, Matthias; Alp, E. Ercan; Hu, Michael Y.; Zhao, Jiyong; Lehnert, Nicolai

doi:10.1039/d4dt01632g

Vibrational properties of heme-nitrosoalkane complexes in comparison with those of their HNO analogs, and reactivity studies towards nitric oxide and Lewis acids

Journal Article · Thu Jul 04 00:00:00 EDT 2024 · Dalton Transactions

DOI:https://doi.org/10.1039/d4dt01632g· OSTI ID:2437655

Harland, Jill B. ^[1]; ^[1]; Thomas, Diamond J. ^[1]; ^[1]; Kampf, Jeff W. ^[1]; Zeller, Matthias ^[2]; Alp, E. Ercan ^[3]; ^[3]; Zhao, Jiyong ^[3]; ^[1]

Univ. of Michigan, Ann Arbor, MI (United States)
Purdue Univ., West Lafayette, IN (United States)
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

C-Nitroso compounds (RNO, R = alkyl and aryl) are byproducts of drug metabolism and bind to heme proteins, and their heme-RNO adducts are isoelectronic to ferrous nitroxyl (NO-/HNO) complexes. Importantly, heme-HNO compounds are key intermediates in the reduction of NO to N₂O and nitrite to ammonium in the nitrogen cycle. Ferrous heme-RNO complexes act as stable analogs of these species, potentially allowing for the investigation of the vibrational and electronic properties of unstable heme-HNO intermediates. In this paper, a series of six-coordinate ferrous heme-RNO complexes (where R = iPr and Ph) were prepared using the TPP^2- and 3,5-Me-BAFP^2- co-ligands, and tetrahydrofuran, pyridine, and 1-methylimidazole as the axial ligands (bound trans to RNO). These complexes were characterized using different spectroscopic methods and X-ray crystallography. The complex [Fe(TPP)(THF)(iPrNO)] was further utilized for nuclear resonance vibrational spectroscopy (NRVS), allowing for the detailed assignment of the Fe–N(R)O vibrations of a heme-RNO complex for the first time. The vibrational properties of these species were then correlated with those of their HNO analogs, using DFT calculations. Our studies support previous findings that RNO ligands in ferrous heme complexes do not elicit a significant trans effect. In addition, the complexes are air-stable, and do not show any reactivity of their RNO ligands towards NO. So although ferrous heme-RNO complexes are suitable structural and electronic models for their HNO analogs, they are unsuitable to model the reactivity of heme-HNO complexes. We further investigated the reaction of our heme-RNO complexes with different Lewis acids. Here, [Fe(TPP)(THF)(iPrNO)] was found to be unreactive towards Lewis acids. In contrast, [Fe(3,5-Me-BAFP)(iPrNO)₂] is reactive towards all of the Lewis acids investigated here, but in most cases the iron center is simply oxidized, resulting in the loss of the iPrNO ligand. In the case of the Lewis acid B₂(pin)₂, the reduced product [Fe(3,5-Me-BAFP)(iPrNH₂)(iPrNO)] was identified by X-ray crystallography.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 2437655

Journal Information:: Dalton Transactions, Journal Name: Dalton Transactions Journal Issue: 33 Vol. 53; ISSN 1477-9226

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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