| 词条 | Trimethylphosphine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 407272775 | ImageFile = PMe3.png | ImageFile_Ref = {{chemboximage|correct|??}} | ImageSize = 200 | ImageName = Stereo, skeletal formula of trimethylphosphine with the lone pair of electrons shown, and all explicit hydrogens added | ImageFile1 = Trimethylphosphine-A-3D-balls.png | ImageFile1_Ref = {{chemboximage|correct|??}} | ImageSize1 = 200 | ImageName1 = Ball and stick model of trimethylphosphine | ImageFile2 = Trimethylphosphine-3D-vdW.png | ImageSize2 = 200 px | PIN = Trimethylphosphane | SystematicName = Trimethylphosphane[1] (substitutive) Trimethylphosphorus[1] (additive) |Section1={{Chembox Identifiers | CASNo = 594-09-2 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 68983 | ChemSpiderID = 62205 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | EINECS = 209-823-1 | UNNumber = 1993 | MeSHName = trimethyl+phosphine | ChEBI = 35890 | ChEBI_Ref = {{ebicite|changed|EBI}} | Beilstein = 969138 | SMILES = CP(C)C | StdInChI = 1S/C3H9P/c1-4(2)3/h1-3H3 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = YWWDBCBWQNCYNR-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} }} |Section2={{Chembox Properties | C=3 | H=9 | P=1 | Appearance = Colorless liquid | Density = 735 mg cm−3 | MeltingPtC = -86 | BoilingPtC = 38 to 39 | VaporPressure = 49.9 kPa (at 20 °C) }} |Section3={{Chembox Structure | Coordination = Trigonal pyramidal | Dipole = 1.19 Debye }} |Section4={{Chembox Hazards | GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|225|315|319|335}} | PPhrases = {{P-phrases|210|261|305+351+338}} | FlashPtC = -19 }} |Section8={{Chembox Related | OtherCompounds = PEt3 NMe3 PH3 PPh3 }} }} Trimethylphosphine is the organophosphorus compound with the formula P(CH3)3, commonly abbreviated as PMe3. This colorless liquid has a strongly unpleasant odor, characteristic of alkylphosphines. The compound is a common ligand in coordination chemistry. Structure and bondingIt is a pyramidal molecule with approximate C3v symmetry. The C–P–C bond angles are approximately 98.6°.[3] The C–P–C bond angles are consistent with the notion that phosphorus predominantly uses the 3p orbitals for forming bonds and that there is little sp hybridization of the phosphorus atom. The latter is a common feature of the chemistry of phosphorus. As a result, the lone pair of trimethylphosphine has predominantly s-character as is the case for phosphine, PH3.[2] PMe3 can be prepared by the treatment of triphenyl phosphite with methylmagnesium chloride:[3] 3 CH3MgCl + P(OC6H5)3 → P(CH3)3 + 3 C6H5OMgCl The synthesis is conducted in dibutyl ether, from which the more volatile PMe3 can be distilled. ReactionsWith a pKa of 8.65, PMe3 reacts with strong acids to give salts [HPMe3]X.[4] This reaction is reversible. WIth strong bases, such as alkyl lithium compounds, a methyl group undergoes deprotonation to give PMe2CH2Li. PMe3 is easily oxidised to the phosphine oxide with oxygen. It reacts with methyl bromide to give tetramethylphosphonium bromide.[5] Coordination chemistryTrimethylphosphine is a highly basic ligand that forms complexes with most metals. As a ligand, trimethylphosphine's Tolman cone angle is 118°.[6] This angle is an indication of the amount of steric protection that this ligand provides to the metal that to which it is bound. Being a relatively compact phosphine, several can bind to a single transition metal, as illustrated by the existence of Pt(PEt3)4.[7] Its complex with silver iodide, AgI(PMe3) is an air-stable solid that releases PMe3 upon heating. SafetyPMe3 is pyrophoric as well as toxic.[9] Trimethylphosphine converts to non-pyrophoric phosphine oxide by treatment with dilute bleach. References1. ^1 {{Cite web|title = Trimethylphosphine (CHEBI:35890)|url = https://www.ebi.ac.uk/chebi/searchId.do?chebiId=35890|work = Chemical Entities of Biological Interest (ChEBI)|publisher = European Bioinformatics Institute|accessdate = 25 September 2011|location = UK|date = 6 June 2006|at = IUPAC Names}} 2. ^E. Fluck, The chemistry of phosphine, Topics in Current Chemistry Vol. 35, 64 pp, 1973. 3. ^{{cite journal | editor = Robert J. Angelici | journal = Inorganic Syntheses |author1=Leutkens, Jr., M. L. |author2=Sattelberger, A. P. |author3=Murray, H. H. |author4=Basil, J. D. |author5=Fackler, Jr. J. P. | year = 1990 | title = Trimethylphosphine | volume = 28 | pages = 305–310 | isbn = 0-471-52619-3 | doi = 10.1002/9780470132593.ch76 | publisher = J. Wiley & Sons | location = New York | series = Inorganic Syntheses}} 4. ^1 Annette Schier and Hubert Schmidbaur"P-Donor Ligands" in Encyclopedia of Inorganic Chemistry 2006, Wiley-VCH, Weinheim. {{DOI|10.1002/0470862106.ia177}} 5. ^{{cite journal|title=Trimethylphosphonium Methylide (Trimethyl Methylenephosphorane)|author=H. F. Klein|year=1978|volume=XVIII|pages=138-140|doi=10.1002/9780470132494.ch23|journal=Inorganic Syntheses}} 6. ^G. L. Miessler and D. A. Tarr Inorganic Chemistry, 3rd Ed, Pearson/Prentice Hall publisher, {{ISBN|0-13-035471-6}}. 7. ^{{cite journal|title=Tetrakis(Triethylphosphine)Platinum(0)|authors=T. Yoshida T. Matsuda S. Otsuka|journal=Inorganic Syntheses|volume=28|year=1990|page=122|doi=10.1002/9780470132593.ch32 }} 8. ^{{cite journal|authors=Sattler, A.; Parkin, G.|title=Formation of a cationic alkylidene complex via formal hydride abstraction: synthesis and structural characterization of [W(PMe3)4([small eta]2-CHPMe2)H]X (X = Br, I)|journal=Chemical Communications |year=2011|volume=47|pages=12828-12830|doi=10.1039/C1CC15457E}} 9. ^http://www.sigmaaldrich.com/catalog/product/aldrich/324116?lang=en®ion=US&cm_sp=Insite-_-prodRecCold_xorders-_-prodRecCold2-2 1 : Tertiary phosphines |
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