Hydroselenide

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Hydroselenide

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Hydroselenide
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29317
ChemSpider	4402037
Gmelin Reference	773467
PubChem CID	5232483
CompTox Dashboard (EPA)	DTXSID901344864
InChI InChI=1S/H2Se/h1H2/p-1 Key: SPVXKVOXSXTJOY-UHFFFAOYSA-M
SMILES [SeH-]
Properties
Chemical formula	HSe⁻
Molar mass	79.980 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

A hydroselenide (or biselenide or selanide) is an ion or chemical compound containing the [SeH]⁻ ion. The radical HSe is a pseudohalogen. Hydroselenide can be a ligand in transition metal complexes where it can be attached to a single atom, or bridge two atoms. The terms used in ligand naming are selanido, or hydrogenselenido.^[1]

Similar compounds include the hydrosulfides, and hydrotellurides. Related compounds include toxic hydrogen selenide gas, hydrodiselenides (HSeSe⁻) and the hydride selenides that do not have a bond between hydrogen and selenium.

Production

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HSe⁻ complexes may be formed by reacting H₂Se with a reduced metal complex, forming a hydrido-hyrogenselenido complex. A halide ligand in a complex may be replaced by HSe⁻ from sodium hydroselenide.

A metal-metal bond can be replaced by a selenium bridge, that can then be protonated to yield a bridged complex.^[2]

Properties

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Hydroselenides easily react with water or water vapour to produce the malodourous hydrogen selenide.

Hydroselenide occurs naturally in alkaline, oxygen-free waters.^[3]

Use

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Hydroselenides have been used to introduce selenium into organic compounds, such as replacing a methylsufide group with selenium.^[4]^[5]

List

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	formula	system	space group	unit cell Å	volume	density	comment	reference
ammonium hydroselenide	[NH₄]SeH						at 24.8°C pressure=14 mm Hg	^[6]
ethylmethylimidazolinium hydroselenide	[(C₂H₅)(CH₃)C₃N₂H₂]⁺SeH⁻	monoclinic	P2₁/n				melt 102°C	^[7]
N-butyl-N-methylpyrollidinium hydroselenide	[(C₄H₉)(CH₃)C4NH₈]⁺SeH⁻						decompose 149°C; slightly greenish	^[7]
sodium hydroselenide	NaSeH	cubic	Fm3m	a=6.26 Z=4	245.3		pale grey; water insensitive	^[8]^[9]^[10]
(tris(Hydrogen 3-p-tolylpyrazolyl)borato)-hydroselenato-magnesium	[Tp^p-Tol]MgSeH	monoclinic	P2₁/n	a=10.870 b=17.015 c=15.907 β=96.39°				^[11]
	LiAlHSeH						grey	^[4]^[12]
^MeL=HC[(CMe)N(2,4,6-Me₃C₆H₂)]₂^–	[^MeLAl(μ-SeH)]₂(μ-Se)						pale yellow; melt 190°C	^[13]
^MeL=HC[(CMe)N(2,4,6-Me₃C₆H₂)]₂^–	[^MeLAl(μ-SeH)]₂(μ-O)•2CH₃C₆H₅	orthorhombic	Pccn	a=21.111 b=13.118 c=20.256 Z=4	5610	1.280	white; decompose 140°C	^[13]
b-diketimi-nato	N(2,6-iPr₂C₆H₃)C(Me)CHC(Me)N(2,6-iPr₂C₆H₃)Al(SeH)₂	orthorhombic	Pnma	a=13.065 b=22.049 c=10.55.7 Z=4	3047	1.318	yellow; decompose 220°C; dimerizes	^[14]
	N(2,6-iPr₂C₆H₃)C(Me)CHC(Me)N(2,6-iPr₂C₆H₃)(HSe)AlSeAl(SeH)N(2,6-iPr₂C₆H₃)C(Me)CHC(Me)N(2,6-iPr₂C₆H₃)	monoclinic	P2₁/n	a=12.255 b=27.347 c=17.753 β=98.29° Z=4	5888	1.273	pale yellow; decompose 250°C	^[14]
tri-n-butyl-methylphosphinium hydroselenide	[(C₄H₉)₃(CH₃)P]⁺SeH⁻						melt 57°C	^[7]
	KSeH	cubic	Fm3m	a=6.87 Z=4	324.2			^[10]
Cp*=(CH₃)₅(C₅H₅)	Cp*₂Ti(SeH)₂							^[15]
	(C₅H₅)₂Ti(SeH)₂							^[15]
	(C₅H₅)₂TiCl(SeH)							^[15]
	PPN[Cr(CO)₅SeH]						yellow; decompose 94°C	^[16]
	PPN[(CO)₅Cr]₂(μ-SeH)							^[16]
	Fe₂(CO)₆(μ₂-SeH)₂							^[16]
	[(C₅H₅)Co]2(μ-P(CH₃)₂)₂(μ-SeH)•PF₆						red-brown	^[17]
	dppeNi(SeH)₂							^[18]
	RbSeH	cubic	Fm3m	a=7.16 Z=4	331.4			^[10]
Cp* = η⁵-C₅Me₅	[(Cp*RhCl)₂(μ-SeH)₂]	orthorhombic	Pccn	a=13.512 b=20.435 c=8.660			red	^[19]
	(CH₂CH₂PPh₂)₃PRhSeH	hexagonal	P6₃	a=13.573 c=12.188 Z=2				^[20]
	(CH₂CH₂PPh₂)₃PRh(SeH){H)CF₃SO₃							^[20]
	CsSeH	cubic	Fm3m	a=4.437 Z=1	87.4			^[10]
	Cp*₂Ta(Se)SeH							^[18]
	AsPh₄[(CO)₅W]₂(μ-SeH)							^[16]
	Re₂(CO)₈(μ₂-SeH)₂						air sensistive	^[16]
	trans-Pt(PEt₃)₂(SeH)₂						yellow; air sensitive	^[18]
	trans-Pt(PEt₃)₂(SeH)₂(H)₂							^[16]
	trans-Pt(PEt₃)₂(SeH)H						white; melt 135°C; air sensitive	^[18]
	PtH(SeH)(PPh₃)₂						air stable;melt 135°C	^[16]
	Pt(PEt₃)₂(SeH)Cl(H)₂							^[2]
	Pt(PEt₃)₂(SeH)Br(H)₂							^[2]
	Pt(PEt₃)₂(SeH)I(H)₂							^[2]
	IrCl(CO)(PPh₃)₂(SeH)(H)						air sensitive; decompose >160°C	^[16]^[2]
Cp* = η⁵-C₅Me₅	[(Cp*IrCl)₂(μ-SeH)₂]						yellow	^[19]
	(t-BuC₅H₄)₂Nb(η²-Te₂)H						dark orange	^[21]
(^AdArO)₃N³⁻ = tris(2-hydroxy-3-adamantyl-5-methylbenzyl)amine)	[((^AdArO)₃N)U(CH₃OC₂H₄OCH₃)(SeH)]							^[22]
	{((^AdArO)₃N)U}₂(μ-SeH)₂							^[22]
(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)-potassium selenido-{2,2',2''-[(1,4,7-triazonane-1,4,7-triyl)tris(methylene)]tris[4-methyl-6-(tricyclo[3.3.1.1^3,7]decan-1-yl)phenolato]}-uranium	((^Ad,MeArO)₃tacn)U(SeH)	hexagonal	P6₃	a=14.920 c=19.254 Z=2	3711.9	1.451	brown	^[23]

References

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^ Gold, Victor, ed. (2019). The IUPAC Compendium of Chemical Terminology: The Gold Book (4 ed.). Research Triangle Park, NC: International Union of Pure and Applied Chemistry (IUPAC). doi:10.1351/goldbook.p04930.
^ ^a ^b ^c ^d ^e Gysling, Henry J. (1986-04-02), Patai, Saul; Rappoport, Zvi (eds.), Ligand properties of organic selenium and tellurium compounds, PATai's Chemistry of Functional Groups, vol. 1 (1 ed.), Wiley, pp. 679–855, doi:10.1002/9780470771761.ch18, ISBN 978-0-471-90425-0, retrieved 2024-05-22
^ Korobova, E. M.; Ryzhenko, B. N.; Cherkasova, E. V.; Sedykh, E. M.; Korsakova, N. V.; Danilova, V. N.; Khushvakhtova, S. D.; Berezkin, V. Yu. (June 2014). "Iodine and selenium speciation in natural waters and their concentrating at landscape-geochemical barriers". Geochemistry International. 52 (6): 500–514. doi:10.1134/S001670291404003X. ISSN 0016-7029.
^ ^a ^b Ishihara, Hideharu; Koketsu, Mamoru; Fukuta, Yoshihisa; Nada, Futoshi (2001-08-01). "Reaction of Lithium Aluminum Hydride with Elemental Selenium: Its Application as a Selenating Reagent into Organic Molecules". Journal of the American Chemical Society. 123 (34): 8408–8409. doi:10.1021/ja005800o. ISSN 0002-7863. PMID 11516295.
^ Ranu, Brindaban C.; Banerjee, Bubun (2020-04-20). Organoselenium Chemistry. Walter de Gruyter GmbH & Co KG. pp. 13–14. ISBN 978-3-11-062229-4.
^ Mikus, F. F.; Poss, F. J. (February 1949). "Equilibrium between Ammonia and Hydrogen Selenide". Journal of the American Chemical Society. 71 (2): 429–431. doi:10.1021/ja01170a017. ISSN 0002-7863.
^ ^a ^b ^c Finger, Lars H.; Sundermeyer, Jörg (2016-03-14). "Halide-Free Synthesis of Hydrochalcogenide Ionic Liquids of the Type [Cation][HE] (E=S, Se, Te)". Chemistry – A European Journal. 22 (12): 4218–4230. doi:10.1002/chem.201504577. ISSN 0947-6539. PMID 26879604.
^ "The Structure of Yttrium Hydride Telluride YHTe from Single-Crystal X-Ray Diffraction Data". Joint Polish-German Crystallographic Meeting, February 24–27, 2020, Wrocław, Poland: 64–65. 24 February 2020. doi:10.1515/9783110692914-002.
^ Młochowski, Jacek; Syper, Ludwik (2001-04-15), John Wiley & Sons, Ltd (ed.), "Sodium Hydrogen Selenide", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rs079, ISBN 978-0-471-93623-7, retrieved 2024-05-22
^ ^a ^b ^c ^d Teichert, Wolfram; Klemm, Wilhelm (1939-11-18). "Zur Kenntnis der Hydrosulfide und Hydroselenide der Alkalimetalle". Zeitschrift für anorganische und allgemeine Chemie. 243 (1): 86–98. doi:10.1002/zaac.19392430108. ISSN 0863-1786.
^ Ghosh, Prasenjit; Parkin, Gerard (1996). "Terminal hydrochalcogenido and bridging selenido derivatives of magnesium supported by tris(3-p-tolylpyrazolyl)hydroborate ligation: the syntheses and structures of [Tp p-Tol]MgEH (E = S, Se) and {[Tp p-Tol]Mg}2Se". Chemical Communications (10): 1239–1240. doi:10.1039/cc9960001239. ISSN 1359-7345.
^ Ranu, Brindaban C.; Banerjee, Bubun (2020-04-20). Organoselenium Chemistry. Walter de Gruyter GmbH & Co KG. pp. 14–15. ISBN 978-3-11-062229-4.
^ ^a ^b González-Gallardo, Sandra; Cruz-Zavala, Aracely S.; Jancik, Vojtech; Cortés-Guzmán, Fernando; Moya-Cabrera, Mónica (2013-03-18). "Preparation of Telluro- and Selenoalumoxanes under Mild Conditions". Inorganic Chemistry. 52 (6): 2793–2795. doi:10.1021/ic302588f. ISSN 0020-1669.
^ ^a ^b Cui, Chunming; Roesky, Herbert W.; Hao, Haijun; Schmidt, Hans-Georg; Noltemeyer, Mathias (2000-05-15). "The First Structurally Characterized Metal–SeH Compounds: [LAl(SeH)2] and [L(HSe)AlSeAl(SeH)L]". Angewandte Chemie International Edition. 39 (10): 1815–1817. doi:10.1002/(SICI)1521-3773(20000515)39:10<1815::AID-ANIE1815>3.0.CO;2-W. PMID 10934372.
^ ^a ^b ^c Bottomley, Frank; Day, Robert W. (August 1991). "Preparation and properties of (.eta.-C5H5)2TiCl(SeH), (.eta.-C5H5)2Ti(SeH)2, [(.eta.-C5H5)Ti]4(.mu.2-Se)3(.mu.3-Se)3, and related cyclopentadienyl selenides of titanium". Organometallics. 10 (8): 2560–2563. doi:10.1021/om00054a012. ISSN 0276-7333.
^ ^a ^b ^c ^d ^e ^f ^g ^h Gysling, H. J. (2 April 1986). "Ligand properties of organic selenium and tellurium compounds". The Chemistry of Organic Selenium and Tellurium Compounds Volume 1. PATai's Chemistry of Functional Groups. Vol. 1. pp. 754–758. doi:10.1002/9780470771761.ch18. ISBN 978-0-471-90425-0.
^ Hofmann, Werner; Werner, Helmut (December 1981). "Electrophilic Addition of a Sulfur, Selenium, and Tellurium Atom as well as of an SO 2 Molecule to a Metal-Metal Bond". Angewandte Chemie International Edition in English. 20 (12): 1014–1016. doi:10.1002/anie.198110142. ISSN 0570-0833.
^ ^a ^b ^c ^d Shin, Jun Ho; Parkin, Gerard (March 1995). "Selenium Complexes of Permethyltantalocene: Interesting Contrasts with Their Tellurium Analogs". Organometallics. 14 (3): 1104–1106. doi:10.1021/om00003a010. ISSN 0276-7333.
^ ^a ^b Seino, Hidetake; Mizobe, Yasushi; Hidai, Masanobu (2000-09-01). "Preparation of Dinuclear Rhodium and Iridium Complexes with Two Bridging Hydroselenido Ligands and Their Conversion into Tri- and Tetranuclear Selenido Clusters". Organometallics. 19 (18): 3631–3639. doi:10.1021/om0004040. ISSN 0276-7333.
^ ^a ^b Di Vaira, Massimo; Peruzzini, Maurizio; Stoppioni, Piero (March 1991). "Hydrochalcogenide and hydride hydrochalcogenide derivatives of rhodium". Inorganic Chemistry. 30 (5): 1001–1007. doi:10.1021/ic00005a024. ISSN 0020-1669.
^ Ebner, Alexander; Meier, Walter; Mugnier, Yves; Wachter, Joachim (July 2007). "Investigation into the reaction of (t-BuC5H4)2Nb(η2-Te2)H with CH3Li: Hydride abstraction versus telluride methylation". Inorganica Chimica Acta. 360 (10): 3330–3334. doi:10.1016/j.ica.2007.03.060.
^ ^a ^b Franke, Sebastian M.; Rosenzweig, Michael W.; Heinemann, Frank W.; Meyer, Karsten (2015). "Reactivity of uranium( iii ) with H 2 E (E = S, Se, Te): synthesis of a series of mononuclear and dinuclear uranium( iv ) hydrochalcogenido complexes". Chemical Science. 6 (1): 275–282. doi:10.1039/C4SC02602K. ISSN 2041-6520. PMC 5811169. PMID 29560170.
^ Rosenzweig, Michael W.; Hümmer, Julian; Scheurer, Andreas; Lamsfus, Carlos Alvarez; Heinemann, Frank W.; Maron, Laurent; Mazzanti, Marinella; Meyer, Karsten (2019). "A complete series of uranium( iv ) complexes with terminal hydrochalcogenido (EH) and chalcogenido (E) ligands E = O, S, Se, Te". Dalton Transactions. 48 (29): 10853–10864. doi:10.1039/C9DT00530G. ISSN 1477-9226. PMID 30950469.

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