Hydroselenide
Identifiers
ChEBI
ChemSpider
773467
InChI=1S/H2Se/h1H2/p-1
Key: SPVXKVOXSXTJOY-UHFFFAOYSA-M
Properties
H Se −
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).
Chemical compound
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 H2 Se 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
[(C2 H5 )(CH3 )C3 N2 H2 ]+ SeH−
monoclinic
P 21 /n
melt 102°C
[ 7]
N -butyl-N -methylpyrollidinium hydroselenide
[(C4 H9 )(CH3 )C4NH8 ]+ SeH−
decompose 149°C; slightly greenish
[ 7]
sodium hydroselenide
NaSeH
cubic
Fm 3 m
a=6.26 Z=4
245.3
pale grey; water insensitive
[ 8] [ 9] [ 10]
(tris(Hydrogen 3-p-tolylpyrazolyl)borato)-hydroselenato-magnesium
[Tpp -Tol ]MgSeH
monoclinic
P 21 /n
a =10.870 b =17.015 c= 15.907 β =96.39°
[ 11]
LiAlHSeH
grey
[ 4] [ 12]
Me L=HC[(CMe)N(2,4,6-Me3 C6 H2 )]2 –
[Me LAl(μ-SeH)]2 (μ-Se)
pale yellow; melt 190°C
[ 13]
Me L=HC[(CMe)N(2,4,6-Me3 C6 H2 )]2 –
[Me LAl(μ-SeH)]2 (μ-O)•2CH3 C6 H5
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-i Pr2 C6 H3 )C(Me)CHC(Me)N(2,6-i Pr2 C6 H3 )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-i Pr2 C6 H3 )C(Me)CHC(Me)N(2,6-i Pr2 C6 H3 )(HSe)AlSeAl(SeH)N(2,6-i Pr2 C6 H3 )C(Me)CHC(Me)N(2,6-i Pr2 C6 H3 )
monoclinic
P 21 /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
[(C4 H9 )3 (CH3 )P]+ SeH−
melt 57°C
[ 7]
KSeH
cubic
Fm 3 m
a=6.87 Z=4
324.2
[ 10]
Cp*=(CH3 )5 (C5 H5 )
Cp*2 Ti(SeH)2
[ 15]
(C5 H5 )2 Ti(SeH)2
[ 15]
(C5 H5 )2 TiCl(SeH)
[ 15]
PPN[Cr(CO)5 SeH]
yellow; decompose 94°C
[ 16]
PPN[(CO)5 Cr]2 (μ-SeH)
[ 16]
Fe2 (CO)6 (μ2 -SeH)2
[ 16]
[(C5 H5 )Co]2(μ-P(CH3 )2 )2 (μ-SeH)•PF6
red-brown
[ 17]
dppeNi(SeH)2
[ 18]
RbSeH
cubic
Fm 3 m
a=7.16 Z=4
331.4
[ 10]
Cp* = η5 -C5 Me5
[(Cp*RhCl)2 (μ-SeH)2 ]
orthorhombic
Pccn
a =13.512 b =20.435 c =8.660
red
[ 19]
(CH2 CH2 PPh2 )3 PRhSeH
hexagonal
P 63
a=13.573 c=12.188 Z=2
[ 20]
(CH2 CH2 PPh2 )3 PRh(SeH){H)CF3 SO3
[ 20]
CsSeH
cubic
Fm 3 m
a=4.437 Z=1
87.4
[ 10]
Cp*2 Ta(Se)SeH
[ 18]
AsPh4 [(CO)5 W]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 -C5 Me5
[(Cp*IrCl)2 (μ-SeH)2 ]
yellow
[ 19]
(t -BuC5 H4 )2 Nb(η2 -Te2 )H
dark orange
[ 21]
(Ad ArO)3 N3− = tris(2-hydroxy-3-adamantyl-5-methylbenzyl)amine)
[((Ad ArO)3 N)U(CH3 OC2 H4 OCH3 )(SeH)]
[ 22]
{((Ad ArO)3 N)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[3.3.1.13,7 ]decan-1-yl)phenolato]}-uranium
((Ad,Me ArO)3 tacn)U(SeH)
hexagonal
P 63
a =14.920 c =19.254 Z=2
3711.9
1.451
brown
[ 23]
References
^ 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 .