For the functional group, see Diphosphene (functional group).
Diphosphene
Ball and stick model of diphosphene molecule
Ball and stick model of diphosphene molecule
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/H2P2/c1-2/h1-2H checkY
    Key: SWJAOBXRZSMKNS-UHFFFAOYSA-N checkY
  • P=P
Properties
P2H2
Molar mass 63.964 g·mol−1
Related compounds
Other anions
 diazene
Other cations
 diphosphenes
Related Binary azenes
 triazene
tetrazene
Related compounds
 ammonia
diazane
triazane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diphosphene is a compound having the formula (PH)2. It exists as two geometric isomers, E and Z.[1] Diphosphene is also the parent member of the entire class of diphosphene compounds with the formula (PR)2, where R is an organyl group.[2]

Visible radiation induces cis-trans isomerization,[3] although further irradiation can excite the molecule to a triplet diradical state. In triplet trans-HPPH, the P-P bond length is predicted to be 2.291 Å. It is not only longer than the P-P double bond in ground state trans-bis(2,4,6-tri-tert-butylphenyl)diphosphene, but also longer than that of P-P single bond in H2P−PH2. Calculation of the dihedral angle of trans-HPPH suggests that it is almost 90 degree, which means the formation of and P-P bonds is forbidden and σ bond is enhanced.[4]

References

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  1. ^ Lu, T.; Simmonett, A. C.; Evangelista, F. A.; Yamaguchi, Y.; Schaefer, H. F. (2009). "Diphosphene and Diphosphinylidene". The Journal of Physical Chemistry A. 113 (47): 13227–13236. Bibcode:2009JPCA..11313227L. doi:10.1021/jp904028a. PMID 19594123.
  2. ^ Yoshifuji, M.; Shibayama, K.; Inamoto, N.; Hirotsu, K.; Higuchi, T. (1983). "Reaction of the diphosphene ArP=PAr (Ar = 2,4,6-But3C6H2) with sulphur: isolation and X-ray structure of the diphosphene monosulphide". Journal of the Chemical Society, Chemical Communications. 1983 (16): 862–863. doi:10.1039/C39830000862.
  3. ^ Caminade, Anne-Marie; Verrier, Martine; Ades, Claude; Paillous, Nicole; Koenig, Max (1984-01-01). "Laser irradiation of a diphosphene: evidence for the first cis–trans isomerization". J. Chem. Soc., Chem. Commun. (13): 875–877. doi:10.1039/c39840000875. ISSN 0022-4936.
  4. ^ Lu, Tongxiang; Hao, Qiang; Simmonett, Andrew C.; Evangelista, Francesco A.; Yamaguchi, Yukio; Fang, De-Cai; Schaefer, Henry F. (2010-10-14). "Low-Lying Triplet States of Diphosphene and Diphosphinylidene". The Journal of Physical Chemistry A. 114 (40): 10850–10856. Bibcode:2010JPCA..11410850L. doi:10.1021/jp105281w. ISSN 1089-5639. PMID 20836526.
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Diphosphenes

Diphosphene is a type of organophosphorus compound that has a phosphorus–phosphorus double bond, denoted by R-P=P-R'. These compounds are not common,

Phosphorus

A stable diphosphene, a derivative of phosphorus(I)

Hexakis(trimethylphosphine)tungsten

symmetrical and unsymmetrical diphosphenes: The resultant phosphorus-tungsten species can also catalyze the exchange of diphosphene end-groups. The W(PMe3)4(η2-CH2PMe2)H

Phosphine

to contain sodium hydroxide. Diphosphane, H2P−PH2, simplified to P2H4 Diphosphene, HP=PH For further information about the early history of phosphine,

Hydrazine

azanes Ammonia Triazane Related compounds Diazene Triazene Tetrazene Diphosphene Except where otherwise noted, data are given for materials in their standard

Cis–trans isomerism

isomerism can also occur in inorganic compounds. Diazenes (and the related diphosphenes) can also exhibit cis–trans isomerism. As with organic compounds, the

Dimetallene

was later shown to be a cyclic dimer (PhP)4. The first true diphosphene, dimesityl diphosphene, was prepared in 1981. This was shortly followed by the first

Diphosphane

diphosphorus tetraiodide Related compounds phosphane triphosphane diphosphene diphosphenes Except where otherwise noted, data are given for materials in their