Hydroselenide

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.

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.

Properties

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

Hydroselenide occurs naturally in alkaline, oxygen-free waters.

Use

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

List

formula system space group unit cell Å volume density comment reference
ammonium hydroselenide [NH4]SeH at 24.8°C pressure=14 mm Hg
ethylmethylimidazolinium hydroselenide [(C2H5)(CH3)C3N2H2]+SeH− monoclinic P21/n melt 102°C
N-butyl-N-methylpyrollidinium hydroselenide [(C4H9)(CH3)C4NH8]+SeH− decompose 149°C; slightly greenish
sodium hydroselenide NaSeH cubic Fm3m a=6.26 Z=4 245.3 pale grey; water insensitive
(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°
LiAlHSeH grey
MeL=HC[(CMe)N(2,4,6-Me3C6H2)]2– [MeLAl(μ-SeH)]2(μ-Se) pale yellow; melt 190°C
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
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
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
tri-n-butyl-methylphosphinium hydroselenide [(C4H9)3(CH3)P]+SeH− melt 57°C
KSeH cubic Fm3m a=6.87 Z=4 324.2
Cp*=(CH3)5(C5H5) Cp*2Ti(SeH)2
(C5H5)2Ti(SeH)2
(C5H5)2TiCl(SeH)
PPN[Cr(CO)5SeH] yellow; decompose 94°C
PPN[(CO)5Cr]2(μ-SeH)
Fe2(CO)6(μ2-SeH)2
[(C5H5)Co]2(μ-P(CH3)2)2(μ-SeH)•PF6 red-brown
dppeNi(SeH)2
RbSeH cubic Fm3m a=7.16 Z=4 331.4
Cp* = η5-C5Me5 [(Cp*RhCl)2(μ-SeH)2] orthorhombic Pccn a=13.512 b=20.435 c=8.660 red
(CH2CH2PPh2)3PRhSeH hexagonal P63 a=13.573 c=12.188 Z=2
(CH2CH2PPh2)3PRh(SeH){H)CF3SO3
CsSeH cubic Fm3m a=4.437 Z=1 87.4
Cp*2Ta(Se)SeH
AsPh4[(CO)5W]2(μ-SeH)
Re2(CO)8(μ2-SeH)2 air sensitive
trans-Pt(PEt3)2(SeH)2 yellow; air sensitive
trans-Pt(PEt3)2(SeH)2(H)2
trans-Pt(PEt3)2(SeH)H white; melt 135°C; air sensitive
PtH(SeH)(PPh3)2 air stable;melt 135°C
Pt(PEt3)2(SeH)Cl(H)2
Pt(PEt3)2(SeH)Br(H)2
Pt(PEt3)2(SeH)I(H)2
IrCl(CO)(PPh3)2(SeH)(H) air sensitive; decompose >160°C
Cp* = η5-C5Me5 [(Cp*IrCl)2(μ-SeH)2] yellow
(t-BuC5H4)2Nb(η2-Te2)H dark orange
(AdArO)3N3− = tris(2-hydroxy-3-adamantyl-5-methylbenzyl)amine) [((AdArO)3N)U(CH3OC2H4OCH3)(SeH)]
{((AdArO)3N)U}2(μ-SeH)2
(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

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. 1 2 3 4 5 Gysling, Henry J. (1986-04-02), "Ligand properties of organic selenium and tellurium compounds", in Patai, Saul; Rappoport, Zvi (eds.), Organic Selenium and Tellurium Compounds (1986), 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. Bibcode:2014GeocI..52..500K. doi:10.1134/S001670291404003X. ISSN 0016-7029.
  4. 1 2 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. Bibcode:2001JAChS.123.8408I. 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. Bibcode:1949JAChS..71..429M. doi:10.1021/ja01170a017. ISSN 0002-7863.
  7. 1 2 3 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), "Sodium Hydrogen Selenide", in John Wiley & Sons, Ltd (ed.), 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. 1 2 3 4 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.
  11. ↑ 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.
  12. ↑ 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.
  13. 1 2 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. PMID 23458274.
  14. 1 2 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.
  15. 1 2 3 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.
  16. 1 2 3 4 5 6 7 8 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.
  17. ↑ 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.
  18. 1 2 3 4 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.
  19. 1 2 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.
  20. 1 2 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.
  21. ↑ 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.
  22. 1 2 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.
  23. ↑ 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.