Bis(diphenylphosphino)methane
<templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox SDSTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | White crystalline powder |
| Melting point | Template:Chembox CalcTemperatures |
Template:Chembox Footer/trackingScript error: No such module "TemplatePar".Template:Short description
1,1-Bis(diphenylphosphino)methane (dppm), is an organophosphorus compound with the formula CH2(PPh2)2. Dppm, a white, crystalline powder, is used in inorganic and organometallic chemistry as a ligand.[1] It is more specifically a chelating ligand because it is a ligand that can bond to metals with two phosphorus donor atoms. The natural bite angle is 73°.[2]
Synthesis and reactivity
1,1-Bis(diphenylphosphino)methane was first prepared by the reaction of sodium diphenylphosphide (Ph2PNa) with dichloromethane:[3]
- Ph3P + 2 Na → Ph2PNa + NaPh
- 2NaPPh2 + CH2Cl2 → Ph2PCH2PPh2 + 2 NaCl
The methylene group (CH2) in dppm (and especially its complexes) is mildly acidic. The ligand can be oxidized to give the corresponding oxides and sulfides CH2[P(E)Ph2]2 (E = O, S). The methylene group is even more acidic in these derivatives.
Coordination chemistry
As a chelating ligand, 1,1-bis(diphenylphosphino)methane forms a four-membered ring with the constituents MP2C. The ligand promotes the formation of bimetallic complexes that feature five-membered M2P2C rings. In this way, dppm promotes the formation of bimetallic complexes. One such example is the dipalladium chloride, Pd2Cl2(dppm)2. In this complex, the oxidation state for the Pd centres are I. Bis(diphenylphosphino)methane gives rise to a family of coordination compounds known as A-frame complexes.[4]
2-from-xtal-3D-ball-stick-hybrid.png){kind=link}
References
<templatestyles src="Reflist/styles.css" />
Script error: No such module "Check for unknown parameters".