Chemistry:Sodium diethyldiselenocarbamate

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Sodium diethyldiselenocarbamate
Identifiers
3D model (JSmol)
Properties
C5H10NNaSe2
Molar mass 265.074 g·mol−1
Appearance yellow solid
Melting point 100–101 °C (212–214 °F; 373–374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sodium diethyldiselenocarbamate is the organoselenium compound with the formula (CH
3
CH
2
)
2
NCSe
2
Na+
. It is a deep yellow, water soluble salt. It is one of the best studied diselenocarbamates, otherwise a rare class of compounds.[1]

Preparation and reactions

Sodium diethyldiselenocarbamate is obtained by treating carbon diselenide with diethylamine in the presence of sodium hydroxide:[2]

CSe2 + HN(C2H5)2 + NaOH → NaSe2CN(C2H5)2 + H2O

Other diselenocarbamates can be prepared similarly from secondary amines and carbon diselenide. The related diselenoxanthates have also been prepared.[2]

Diethyldiselenocarbamate forms coordination complexes with many transition metals.[1] With Se(II), it forms the bicyclic Se(Se2CN(C2H5)2)2.[3]

Structure and bonding

The C2NCSe2 core of the diethyldiselenocarbamate anion and its complexes is planar, indicating some C–N multiple bond character.[4]

See also

References

  1. 1.0 1.1 Pan, Wie-Hin; Fackler, John P. (1982). "2. Diselenocarbamates from Carbon Diselenide". Diselenocarbamates from Carbon Diselenide. Inorganic Syntheses. 21. pp. 6–11. doi:10.1002/9780470132524.ch2. ISBN 978-0-471-86520-9. 
  2. 2.0 2.1 Rosenbaum, A.; Kirchberg, H.; Leibnitz, E. (1963). "Über Diselenoxanthogenate und Diselenocarbamate". Journal für Praktische Chemie 19 (1–2): 1–13. doi:10.1002/prac.19630190101. 
  3. Gould, Robert O.; Jones, C. Lynn; Savage, W. John; Stephenson, T. Anthony (1976). "Crystal and Molecular Structure of Bis(NN-diethyldiselenocarbamato)-selenium(II)". Journal of the Chemical Society, Dalton Transactions (10): 908. doi:10.1039/dt9760000908. 
  4. Dietzsch, Wolfgang; Duffy, Norman V.; Lee, Aaron M.; Skelton, Brian W.; White, Allan H. (2006). "Structural Consequences of S → Se Substitution in some Symmetrical [M(S2CNR2)3] Complexes". Zeitschrift für Anorganische und Allgemeine Chemie 632 (15). doi:10.1002/zaac.200600207.