| Revision as of 05:44, 25 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|err← Previous edit |
Latest revision as of 11:38, 28 October 2024 edit undoM97uzivatel (talk | contribs)Extended confirmed users6,558 edits →Synthesis: simpler link |
| (58 intermediate revisions by 27 users not shown) |
| Line 1: |
Line 1: |
|
{{Chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 422818404 |
|
|
| ImageFileL1 = Diphosphorus-2D-dimensions.png |
|
| verifiedrevid = 446607833 |
|
|
| ImageFileL1 = Diphosphorus-2D-dimensions.png |
|
| ImageNameL1 = Stick model of diphosphorus |
|
| ImageNameL1 = Stick model of diphosphorus |
|
| ImageFileR1 = Diphosphorus-3D-vdW.png |
|
| ImageFileR1 = Diphosphorus-3D-vdW.png |
|
| ImageNameR1 = Spacefill model of diphosphorus |
|
| ImageNameR1 = Spacefill model of diphosphorus |
|
| IUPACName = Diphosphorus |
|
| IUPACName = Diphosphorus |
|
|
| SystematicName = Diphosphyne<ref name=EBI /> |
| ⚫ |
| SystematicName = Diphosphyne<ref>{{Cite web|title = Diphosphorus (CHEBI:33472)|url = https://www.ebi.ac.uk/chebi/searchId.do?chebiId=33472|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref> |
|
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo = 12185-09-0 |
|
|
| PubChem = 5460700 |
|
| CASNo = 12185-09-0 |
|
|
| PubChem = 5460700 |
|
| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
|
|
| ChemSpiderID = 4574176 |
|
| ChemSpiderID = 4574176 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI = 33472 |
|
| ChEBI = 33472 |
|
| Gmelin = 1400241 |
|
| Gmelin = 1400241 |
|
| SMILES = P#P |
|
| SMILES = P#P |
|
| StdInChI = 1S/P2/c1-2 |
|
| StdInChI = 1S/P2/c1-2 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| InChI = 1/P2/c1-2 |
|
| InChI = 1/P2/c1-2 |
|
| StdInChIKey = FOBPTJZYDGNHLR-UHFFFAOYSA-N |
|
| StdInChIKey = FOBPTJZYDGNHLR-UHFFFAOYSA-N |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| InChIKey = FOBPTJZYDGNHLR-UHFFFAOYAU |
|
| InChIKey = FOBPTJZYDGNHLR-UHFFFAOYAU |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| P = 2 |
|
| P=2 |
|
| ExactMass = 61.947523024 g mol<sup>-1</sup> |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Diphosphorus''', P<sub>2</sub>, is the ] form of ].<ref>Russell, C. A. (2010), PP, a Laboratory Reagent?. Angewandte Chemie International Edition, 49: 9572–9573. {{doi|10.1002/anie.201006243}}</ref> Unlike its ] neighbor ] which forms a stable N<sub>2</sub> molecule with a nitrogen to nitrogen ], phosphorus prefers a tetrahedral form P<sub>4</sub> because P-P ]s are high in energy. Diphosphorus is therefore very reactive with a ] (117 ]/] or 490 ]/mol) half that of ]. |
|
'''Diphosphorus''' is an ] ] with the ] {{Chem|P|2}}. Unlike nitrogen, its lighter ] neighbor which forms a stable N<sub>2</sub> molecule with a nitrogen to nitrogen ], phosphorus prefers a tetrahedral form P<sub>4</sub> because P-P ]s are high in energy. Diphosphorus is, therefore, very reactive with a ] (117 ]/] or 490 ]/mol) half that of ]. The bond distance has been measured at 1.8934 Å.<ref name=Herzberg /> |
|
|
|
|
|
|
== Synthesis == |
|
Traditionally diphosphorus can be generated by heating ] at 1100 ]s. Nevertheless, some advancements were obtained in generating the diatomic molecule in homogeneous solution, under normal conditions with the use by some ] ] (based on for example ] and ]).<ref>''Triple-Bond Reactivity of Diphosphorus Molecules'' Nicholas A. Piro, Joshua S. Figueroa, Jessica T. McKellar, Christopher C. Cummins ] 1 September '''2006''':Vol. 313. no. 5791, pp. 1276–1279 ]</ref><ref>http://www.sciencemag.org/cgi/reprint/313/5791/1276.pdf</ref> |
|
|
|
Diphosphorus has been generated by heating ] at 1100 ]s (827 ]). Nevertheless, some advancements have been obtained in generating the diatomic molecule in homogeneous solution under normal conditions with the use of some ] ] (based on, for example, ] and ]).<ref name="Piro2006" /> Methods for dissociation of bonds in P<sub>4</sub> molecules via ] were also proposed.<ref name="PhotoexcitedTetraphosphorus1">{{cite journal |author=Lee-Ping Wangb |author2=Daniel Tofana |author3=Jiahao Chena |author4=Troy Van Voorhisa |author5=Christopher C. Cummins |name-list-style=amp | url=http://pubs.rsc.org/en/content/articlehtml/2013/ra/c3ra43940b | title=A pathway to diphosphorus from the dissociation of photoexcited tetraphosphorus |journal=RSC Advances | publisher=Royal Society of Chemistry | date=September 2013 |volume=3 |issue=45 |page=23166 |doi=10.1039/C3RA43940B |bibcode=2013RSCAd...323166W | archive-url=https://web.archive.org/web/20170721124010/https://dspace.mit.edu/openaccess-disseminate/1721.1/90977 | archive-date=2017-07-21 | access-date=2017-07-21 |doi-access=free |hdl=1721.1/90977 |hdl-access=free}}</ref> |
|
|
|
|
|
The molecule attracted attention in 2006 when a new method for its synthesis at milder temperatures emerged.<ref>''Triple-Bond Reactivity of Diphosphorus Molecules'' Nicholas A. Piro, Joshua S. Figueroa, Jessica T. McKellar, Christopher C. Cummins ] 1 September '''2006''':Vol. 313. no. 5791, pp. 1276 - 1279 {{doi|10.1126/science.1129630}} PMID 16946068</ref> |
|
The molecule attracted attention in 2006, when a new method for its synthesis at milder temperatures emerged.<ref name="Piro2006" /> This method is a variation on nitrogen expulsion in ]s with formation of a ]. The synthesis of the diphosphorus precursor consists of reacting a terminal ] ] with a chloroiminophosphane: |
|
|
|
|
This method is a variation on nitrogen expulsion in ]s with formation of a ]. The synthesis of the diphosphorus precursor consists of reacting a terminal ] ] with a chloroiminophosphane: |
|
|
|
|
|
|
:] |
|
:] |
|
|
|
|
|
Heating this compound at 50 °C in ] serving as a ] and as a ], expulses diphosphorus which reactive as it is forms a double ] and the niobium imido compound: |
|
Heating this compound at 50 °C in ] serving as a ] and as a ] expels diphosphorus, which is reactive, as the end products are a double ] and the niobium imido compound: |
|
|
|
|
|
:] |
|
:] |
|
|
|
|
|
The same imido compound also forms when the ] is performed in ] but then the fate of diphosphorus is unknown. |
|
The same imido compound also forms when the ] is performed in ], but in this case the fate of the diphosphorus is unknown. |
|
|
|
|
|
P<sub>2</sub> has been suggested to form as an intermediate in the ] of P<sub>4</sub> <ref>''Optische und photochemische versuche mit phosphor'' G. Rathenau Physica Volume 4, Issue 6, June 1937, Pages 503-514 {{doi|10.1016/S0031-8914(37)80084-1}}</ref> and in the presence of 2,3-dimethylbutadiene the diphosphane is again formed <ref>Tofan, D. and Cummins, C. C. (2010), ''Photochemical Incorporation of Diphosphorus Units into Organic Molecules''. Angewandte Chemie International Edition, 49: 7516–7518. doi: 10.1002/anie.201004385</ref> To date, no direct evidence of P<sub>2</sub> formation via P<sub>4</sub> photolysis exists. |
|
P<sub>2</sub> has been suggested to form as an intermediate in the ] of P<sub>4</sub>,<ref name=Rathenau1937 /> and in the presence of ] the diphosphane resulting from Diels–Alder addition is again formed.<ref name=Tofan2010 /> To date, no direct evidence of P<sub>2</sub> formation via P<sub>4</sub> photolysis exists. |
|
|
|
|
|
|
The generation of diphosphorus from a diphosphorus bisanthracene adduct has been reported.<ref name=velian2014 /> The synthesis of a stabilized HP<sub>2</sub><sup>+</sup> cation has been reported.<ref name=wang /> |
|
==References== |
|
|
{{Reflist}} |
|
|
|
|
|
|
==External links== |
|
== References == |
|
|
{{reflist|colwidth=30em |
| ⚫ |
*Ron Dagani, "A Mild Route To P2'', '']'' September 4, 2006 |
|
|
|
|refs= |
|
⚫ |
<ref name=EBI>{{cite web|title = Diphosphorus (CHEBI:33472)|url = https://www.ebi.ac.uk/chebi/searchId.do?chebiId=33472|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref> |
|
|
<ref name=Herzberg>{{cite book|author=Huber, K. P.|author2=Herzberg, G. |title=Molecular Spectra and Molecular Structure IV. Constants of Diatomic Molecules |publisher=Van Nostrand |location=New York |year=1979 |isbn= 978-0442233945|title-link=Molecular Spectra and Molecular Structure IV. Constants of Diatomic Molecules }}</ref> |
|
|
<ref name=Piro2006>{{cite journal|last1=Piro|first1=Nicholas A.|last2=Figueroa |first2=Joshua S. | last3=McKellar |first3=Jessica T. |last4=Cumnins |first4=Christopher C.|s2cid=27740669|title=Triple-Bond Reactivity of Diphosphorus Molecules|journal=Science|date=1 September 2006|volume=313|issue=5791|pages=1276–1279|doi=10.1126/science.1129630|pmid=16946068|bibcode = 2006Sci...313.1276P }}</ref> |
|
|
<ref name=Rathenau1937>{{cite journal|last=Rathenau|first=G.|title=Optische und photochemische versuche mit phosphor|journal=Physica|date= June 1937 |volume=4|issue=6|pages=503–514|doi=10.1016/S0031-8914(37)80084-1|trans-title=Optical and photochemical trials with phosphorus|language=German|bibcode=1937Phy.....4..503R}}</ref> |
|
|
<ref name=Tofan2010>{{cite journal|last1=Tofan|first1=Daniel|last2=Cummins |first2=Christopher C.|title=Photochemical incorporation of diphosphorus units into organic molecules|journal=Angewandte Chemie International Edition|date=26 August 2010|volume=49|issue=41|pages=7516–7518|doi=10.1002/anie.201004385|pmid=20799313}}</ref> |
|
|
<ref name=velian2014>''A Retro Diels–Alder Route to Diphosphorus Chemistry: Molecular Precursor Synthesis, Kinetics of P2 Transfer to 1,3-Dienes, and Detection of P2 by Molecular Beam Mass Spectrometry'' |
|
|
Alexandra Velian, Matthew Nava, Manuel Temprado, Yan Zhou, Robert W. Field, and Christopher C. Cummins Journal of the American Chemical Society 2014 136 (39), 13586-13589 {{doi|10.1021/ja507922x}}</ref> |
|
|
<ref name=wang>''Protonation of carbene-stabilized diphosphorus: complexation of HP2+'' Yuzhong Wang, Hunter P. Hickox, Yaoming Xie, Pingrong Wei, Dongtao Cui, Melody R. Walter, Henry F. Schaefer III and Gregory H. Robinson Chem. Commun., 2016, {{doi|10.1039/C6CC01759B}}</ref> |
|
|
|
|
|
|
}} |
| ⚫ |
] |
|
|
|
|
|
|
|
== External links == |
|
] |
|
|
|
|
|
] |
|
|
⚫ |
*Ron Dagani, "A Mild Route To P2", '']'' September 4, 2006 |
|
|
*Carmen Drahl "Flash Of Phosphorus Chemistry Innovation", '']'' September 13, 2010 |
|
|
|
|
|
{{Diatomic elements}} |
|
|
|
|
⚫ |
] |
|
|
] |