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Hydrosulfide Complexes of the Transition Elements: Diverse Roles in Bioinorganic, Cluster, Coordination, and Organometallic Chemistry

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Hydrosulfide Complexes of the Transition Elements: Diverse Roles in Bioinorganic, Cluster, Coordination, and Organometallic Chemistry Chemical Society Reviews Hydrosulfide Complexes of the Transition Elements: Diverse Roles in Bioinorganic, Cluster, Coordination, and Organometallic Chemistry Journal: Chemical Society Reviews Manuscript ID CS-SYN-08-2019-000570.R2 Article Type: Review Article Date Submitted by the 25-Mar-2020 Author: Complete List of Authors: Pluth, Michael; University of Oregon, Chemistry and Biochemistry Tonzetich, Zachary; University of Texas at San Antonio, Chemistry Page 1 of 195 Chemical Society Reviews Hydrosulfide Complexes of the Transition Elements: Diverse Roles in Bioinorganic, Cluster, Coordination, and Organometallic Chemistry Michael D. Plutha,‡ and Zachary J. Tonzetichb,‡ a Department of Chemistry and Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, Institute of Molecular Biology, University of Oregon, Eugene, OR 97403 USA. b Department of Chemistry, University of Texas at San Antonio, San Antonio, TX 78249 USA. 1 Chemical Society Reviews Page 2 of 195 Abstract Sulfur-based ligands are versatile donors that play important roles in a wide array of subdisciplines of inorganic chemistry including organometallic chemistry, bioinorganic chemistry, and cluster science. Despite the breadth of compounds containing sulfur-based ligands, those containing the simplest mercapto group, hydrosulfide ion (HS−), are significantly less developed. – The acceptance of H2S/HS as important biological signaling compounds during the last decade have engendered a renewed interest in the chemistry of H2S and the hydrosulfide ion. Bioinorganic reactivity of hydrosulfide, however, is only one aspect of its fascinating chemistry, much of which revolves around its interactions with transition metal ions. The coordination of HS− to d-block elements produces a unique class of substances that differ in significant ways from more ubiquitous metal thiolates. This review examines the preparation, structure, spectroscopy, and reactivity of such compounds and the roles they play across several fields of chemistry including biological, organometallic, and coordination chemistry 2 Page 3 of 195 Chemical Society Reviews 1. Introduction The chemistry of thiolate ligands has occupied a central place in the consciousness of coordination chemists from the very earliest days of the field.1-5 These versatile ligands find numerous roles across the subdisciplines of inorganic chemistry from organometallics and bioinorganic chemistry, to cluster science. Yet despite the wealth of compounds reported to date featuring thiolate ligands, those containing the simplest sulfhydryl group, hydrosulfide ion (HS−), have been mostly relegated to the status of curiosities. The lack of prominence of the hydrosulfide ion in inorganic chemistry is especially surprising given that its lighter congener, hydroxide (HO−), is among the most commonly encountered ligands in coordination complexes. Challenges associated with manipulating HS− account in large part for this discrepancy. Unlike hydroxide, the conjugate acid of hydrosulfide, H2S, is a toxic gas and not a component of typical reaction milieus. Moreover, the ability of sulfur to catenate provides a myriad of decomposition pathways for hydrosulfide complexes that are not relevant in the chemistry of hydroxide. In addition, monometallic metal hydrosulfides often are functional intermediates en route to formation of multimetallic sulfide-bridged complexes, which further complicates isolation and characterization in non-equilibrium mixtures. In many cases, the use of sterically- hindered ligands has enabled the formation of otherwise unisolable complexes. These challenges notwithstanding, the coordination − chemistry of hydrosulfide ion and related hydropolysulfides (HSn ) has played an important, albeit underappreciated, role in the development of several areas of molecular science. Recently, renewed focus has been cast on the chemistry of hydrosulfide ion and related small sulfur- containing molecules as the importance of H2S as a physiological signaling agent has gained attention.6-12 Biological roles for the hydrosulfide ion, however, encompass only one aspect of its fascinating chemistry. By in large, this chemistry has revolved around its interactions with 3 Chemical Society Reviews Page 4 of 195 transition metal ions. The coordination of HS− to d-block elements produces a unique class of substances that differ in significant ways from more ubiquitous metal thiolates. This review will examine the preparation, structure, spectroscopy, and reactivity of such compounds and the roles they play across several fields of chemistry. Transition metal hydrosulfide complexes are defined as those substances possessing at least one ligand of formula HS−. They can be distinguished from metal thiolates and metal sulfides by the presence of a hydrogen atom on sulfur. In the present review, we have elected to focus on examples of these compounds that have been isolated and characterized unambiguously, ideally through structural means, with particular emphasis on identification of the sulfur-bound H atom. We also pay mind to complexes of hydrogen sulfide (H2S), as these species share many of the same features as their hydrosulfide counterparts. Not covered here are species generated transiently in the gas phase or in low-temperature matrices. We note that this field was reviewed previously nearly two decades ago in a pair of articles published in 2001.13, 14 Since that time, several other reviews have appeared which tangentially cover specific aspects of hydrosulfide complexes.9, 15, 16 However, no comprehensive treatment of this area has appeared in the intervening 19 years to account for new developments in the field and highlight the common themes encountered in the chemistry of this unique class of ligands. In the following contribution, we have elected to organize the review not by element, but instead by the roles played by transition metal hydrosulfide complexes in different areas of chemistry. 1. Definition and Basic Properties of Sulfur, H2S, and Hydrosulfide Ligands. Sulfur is the 10th most abundant element in the universe and 15th most abundant element in Earth’s outer crust.17 When comparing basic physical properties, sulfur is more polarizable than 4 Page 5 of 195 Chemical Society Reviews oxygen, larger (covalent radius: 106 versus 66 pm), and less electronegative (2.58 versus 3.44; Pauling electronegativity scale).18 Sulfur has a wide range of accessible oxidation states, ranging 2– from −2 in thiols and H2S to +6 in sulfate. In its reduced S state, sulfur commonly forms bonds with hydrogen, carbon, or electropositive metals to form thioethers, thiols/H2S, or metal sulfides, – + – respectively. Hydrosulfide has a concerted two-electron reduction potential E°′(HS2 , H /2HS ) of −0.230 V (versus SHE),19 which is similar to that for cysteine E°′(cystine/cysteine) = −0.245 V.20 The one-electron reduction potential for hydrosulfide E°′(S•–, H+/HS–) of +0.92 V21 is also close • + 19 to that for cysteine (E°′(RS , H /RSH) = ~+0.9 V). In aqueous solution, H2S acts as a weak acid – 2– + (pKa = 6.90 at 25 °C; 6.76 at 37 °C) with the second deprotonation event (HS ↔ S + H ) being 22 inaccessible (pKa = 17-19) under normal biological conditions. At physiological pH (7.4 at 37 – °C), H2S exists primarily as HS (~80%), with the remaining 20% in the diprotic, undissociated – form. Because HS is the main physiological form of H2S, this anionic protonation state is likely to affect much of the observed chemical biology of H2S. In aqueous solutions, the distinct – chemistry of H2S versus HS is often difficult to separate due to the rapid equilibration between these two protonation states. To combat this challenge, numerous investigations of biomimetic – inorganic compounds in aprotic solvents have used H2S or organic-soluble forms of HS , such as 23 NBu4SH, to directly probe the differential reactivity. The bond S-H bond dissociation energy of H2S is 90 kcal/mol, which is similar to the metal- sulfur bond strength with many transition metals. This similarity can facilitate the thermodynamic formation metal-sulfur bonds. Moreover, metal sulfides are often highly-insoluble products, with -19 -19 -21 -23 low Ksp values including MnS (7.0 x 10 ), FeS (4.0 x 10 ), NiS (3.0 x 10 ), ZnS (1.6 x 10 ), -37 -49 24 CuS (8.0 x 10 ), and Cu2S (1.2 x 10 ). The nature of these solubility equilibria coupled with the properties of H2S discussed above contribute to the difficulty in isolating well-defined metal 5 Chemical Society Reviews Page 6 of 195 hydrosulfide species. Yet these factors also serve to highlight the importance of understanding the interactions, metals, and ligand environments that facilitate stable metal hydrosulfide formation. 1.2 Binding Modes of HS−. The hydrosulfide ion is capable of both terminal and bridging binding modes (both μ2 and μ3), which is similar to many X-type ligands. In all cases, the unambiguous characterization of hydrosulfide complexes poses a unique challenge given the difficulty in locating H atoms by X- ray crystallography. This situation is made even more difficult in cases where the complex contains other ligands capable of protonation (e.g. oxos, sulfidos, etc.) or when the oxidation state of the metal is ambiguous or not confirmed directly by complementary spectroscopic methods. For complexes with terminal metal sulfide groups, the metal-sulfur bond distance can help to inform whether the sulfur donor is acting as a –1 (e.g. M-SH, M-SR) or –2 (e.g M=S) ligand. Spectroscopic identification
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