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Hydroselenide

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Hydroselenide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
773467
  • InChI=1S/H2Se/h1H2/p-1
    Key: SPVXKVOXSXTJOY-UHFFFAOYSA-M
  • [SeH-]
Properties
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).

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

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

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


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

Use

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

List

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 pale grey; water insensitive [8][9]
(tris(Hydrogen 3-p-tolylpyrazolyl)borato)-hydroselenato-magnesium [Tpp-Tol]MgSeH monoclinic P21/n a=10.870 b=17.015 c=15.907 β=96.39° [10]
LiAlHSeH grey [4][11]
b-diketimi-nato N(2,6-iPr2C6H3)C(Me)CHC(Me)N(2,6-iPr2C6H3)Al(SeH)2 orthorhombic Pnma aˆ=13.065 b=ˆ22.049 c=ˆ10.55.7 Z=ˆ4 ˆ3047 ˆ1.318 yellow; decompose 220°C; dimerizes [12]
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=ˆ27.347 c=ˆ17.753 β=98.29° Zˆ=4 ˆ5888 1.273 pale yellow; decompose 250°C [12]
tri-n-butyl-methylphosphinium hydroselenide [(C4H9)3(CH3)P]+SeH− melt 57°C [7]
Cp*=(CH3)5(C5H5) Cp*2Ti(SeH)2 [13]
(C5H5)2Ti(SeH)2 [14]
(C5H5)2TiCl(SeH) [14]
PPN[Cr(CO)5SeH] yellow; decompose 94°C [15]
PPN[(CO)5Cr]2(μ-SeH) [15]
Fe2(CO)6(μ2-SeH)2 [15]
[(C5H5)Co]2(μ-P(CH3)2)2(μ-SeH)•PF6 red-brown [16]
dppeNi(SeH)2 [17]
Cp* = η5-C5Me5 [(Cp*RhCl)2(μ-SeH)2] orthorhombic Pccn a=13.512 b=20.435 c=8.660 red [18]
(CH2CH2PPh2)3PRhSeH hexagonal P63 a=13.573 c=12.188 Z=2 [19]
(CH2CH2PPh2)3PRh(SeH){H)CF3SO3 [19]
Cp*2Ta(Se)SeH [17]
AsPh4[(CO)5W]2(μ-SeH) [15]
Re2(CO)8(μ2-SeH)2 air sensistive [15]
trans-Pt(PEt3)2(SeH)2 yellow; air sensitive [17]
trans-Pt(PEt3)2(SeH)2(H)2 [15]
trans-Pt(PEt3)2(SeH)H white; melt 135°C; air sensitive [17]
PtH(SeH)(PPh3)2 air stable;melt 135°C [15]
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 [15][2]
Cp* = η5-C5Me5 [(Cp*IrCl)2(μ-SeH)2] yellow [18]
(t-BuC5H4)2Nb(η2-Te2)H dark orange [20]
(AdArO)3N3− = tris(2-hydroxy-3-adamantyl-5-methylbenzyl)amine) [((AdArO)3N)U(CH3OC2H4OCH3)(SeH)] [21]
{((AdArO)3N)U}2(μ-SeH)2 [21]
(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[3.3.1.13,7]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 [22]

References

  1. ^ 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.
  2. ^ 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
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ "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.
  9. ^ 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
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ a b 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.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
  18. ^ 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.
  19. ^ 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.
  20. ^ 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.
  21. ^ 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.
  22. ^ 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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