Ecological Debt Day: Difference between revisions

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{{chembox
| verifiedrevid = 451151193
|  Name = Dimethylphenylphosphine
|  ImageFile = Dimethylphenylphosphine.png
| ImageSize =
|  ImageName = Dimethylphenylphosphine
|  IUPACName = Dimethylphenylphosphane
|  OtherNames = Dimethylphenylphosphine
| Section1 = {{Chembox Identifiers
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62800
| PubChem = 69597
| InChI = 1/C8H11P/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30671
| SMILES = P(c1ccccc1)(C)C
| InChIKey = HASCQPSFPAKVEK-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H11P/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HASCQPSFPAKVEK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 672-66-2
|  EINECS = 211-595-3
  }}
| Section2 = {{Chembox Properties
|  Formula = C<sub>8</sub>H<sub>11</sub>P
|  MolarMass = 138.14 g/mol
|  Appearance = Colorless light pale yellow liquid
|  Density = 0.971 g/cm<sup>3</sup>
|  Solubility = Insoluble
|  MeltingPt = N/A
|  BoilingPt = 74-75°C @ 12 mmHg
  }}
| Section3 = {{Chembox Structure
|  MolShape = Pyramidal
  }}
| Section7 = {{Chembox Hazards
|  ExternalMSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do]
|  FlashPtC = 49
| RPhrases =  {{R10}} {{R36}} {{R37}} {{R38}}
| SPhrases =  {{S26}} {{S36}}
  }}
}}
''' Dimethylphenylphosphine ''' is an [[organophosphorus compound]] with a formula P(C<sub>6</sub>H<sub>5</sub>)(CH<sub>3</sub>)<sub>2</sub>. The [[phosphorus]] is connected to a [[phenyl]] group and two [[methyl]] groups. This colorless air sensitive liquid is commonly used as a [[ligand]] in [[transition metal complex]]es. These complexes are often soluble in organic solvents.


==Preparation==
Dimethylphenylphosphine is prepared by the reaction of [[Grignard reaction|methylmagnesium halide]] with [[dichlorophenylphosphine]].


:(C<sub>6</sub>H<sub>5</sub>)Cl<sub>2</sub>P  +  2CH<sub>3</sub>MgBr  →  (C<sub>6</sub>H<sub>5</sub>)(CH<sub>3</sub>)<sub>2</sub>P  +  2MgBrCl
The main advantage of using the blog is that anyone can use the Word - Press blog and customize the elements in the theme regardless to limited knowledge about internet and website development. It is used by around 25% of all new websites, and there are more than 27 thousand plugins currently available. The effect is to promote older posts by moving them back onto the front page and into the rss feed. If you have any issues with regards to exactly where and how to use [http://iz.sa/wordpressdropboxbackup976682 wordpress backup plugin], you can speak to us at our web-site. Hosted by Your Domain on Another Web Host - In this model, you first purchase multiple-domain webhosting, and then you can build free Wordpress websites on your own domains, taking advantage of the full power of Wordpress. Understanding how Word - Press works can be a challenge, but it is not too difficult when you learn more about it. <br><br>Luckily, for Word - Press users, WP Touch plugin transforms your site into an IPhone style theme. If you wish to sell your services or products via internet using your website, you have to put together on the website the facility for trouble-free payment transfer between customers and the company. You are able to set them within your theme options and so they aid the search engine to get a suitable title and description for the pages that get indexed by Google. It primarily lays emphasis on improving the search engine results of your website whenever a related query is typed in the search box. This can be done by using a popular layout format and your unique Word - Press design can be achieved in other elements of the blog. <br><br>ve labored so hard to publish and put up on their website. When a business benefits from its own domain name and a tailor-made blog, the odds of ranking higher in the search engines and being visible to a greater number of people is more likely. After age 35, 18% of pregnancies will end in miscarriage. Nonetheless, with stylish Facebook themes obtainable on the Globe Broad Internet, half of your enterprise is done previously. Have you heard about niche marketing and advertising. <br><br>Numerous bloggers are utilizing Word - Press and with good reason. php file in the Word - Press root folder and look for this line (line 73 in our example):. Next you'll go by way of to your simple Word - Press site. A whole lot worse, your site will likely be useless as well as your merchandise won't sell if no one has the endurance to wait for the web pages to load. Now all you have to do is log into your Word - Press site making use of the very same username and password that you initially had in your previous site. <br><br>More it extends numerous opportunities where your firm is at comfort and rest assured of no risks & errors. An ease of use which pertains to both internet site back-end and front-end users alike. By the time you get the Gallery Word - Press Themes, the first thing that you should know is on how to install it. Page speed is an important factor in ranking, especially with Google. Definitely when you wake up from the slumber, you can be sure that you will be lagging behind and getting on track would be a tall order.
 
The [[phosphine]] is purified by distillation under reduced pressure.<ref>C. Frajerman; B. Meunier; M. E. Strem., ''Inorganic Syntheses'', Preparation of Dimethylphenylphosphine, 2007, volume 22, 133-135, {{DOI|10.1002/9780470132531}}. ch29</ref>
A solution of (C<sub>6</sub>H<sub>5</sub>)(CH<sub>3</sub>)<sub>2</sub>P in CDCl<sub>3</sub> shows [[proton NMR]] signals at δ = 7.0-7.5 and a doublet at δ = 1.2. The [[phosphorus-31 NMR]] spectrum shows a singlet at -45.89 ppm in CDCl<sub>3</sub>.<ref>Laszlo T. Mika, Laszlo Orha, Norbert Farkas and Istvan T. Horvath, Organometallics, 2009, 28, 1593</ref>
 
==Structure and properties==
Dimethylphenylphosphine is a [[Trigonal pyramidal molecular geometry|pyramidal molecule]] where the [[phenyl]] group and two [[methyl]] groups are connected to the phosphorus. The [[bond length]] and angles are the following: P-C<sub>Me</sub>: 1.844, P-C<sub>Ph</sub>: 1.845 Å, C-C: 1.401 Å, C-H<sub>Me</sub>: 1.090 Å, C-H<sub>Ph</sub>: 1.067 Å, C-P-C: 96.9°, C-P-C (ring): 103.4°, P-C-H: 115.2°.<ref>Novikov, V.P., Kolomeets, V.I., Syshchikov, Yu.N., Vilkov, L.V., Yarkov, A.V., Tsvetkov, E.N., Raevskii, O.A.: Zh. Strukt. Khim., ''J. Struc. Chem''., Investigation of structure of dimethylphenylphosphine by means of gas-phase electron diffraction and vibrational spectroscopy, 1984, volume 25, No.5, 688. {{DOI|10.1007/BF00747909}}</ref>
 
==Comparisons with related phosphine ligands==
The υ<sub>CO</sub> of Ir-Cl(CO)(PPh<sub>3</sub>)<sub>2</sub> and Ir-Cl(CO)(PMe<sub>2</sub>Ph)<sub>2</sub>  are both at 1960&nbsp;cm<sup>−1</sup>, whereas the υ<sub>CO</sub> for Ir-Cl(CO)(PMe<sub>3</sub>)<sub>2</sub> is at 1938&nbsp;cm<sup>−1</sup>.<ref>S.A. Cotton, Chemistry of Precious Metals., 1997, 152-157, ISBN 0-7514-0413-6, ISBN 978-0-7514-0413-5</ref><ref>A.R. Norrris ; J.A.V. Kessel, ''Canadian Journal of Chemistry'', Oxidative addition of 3,5-Dinitrobenzoyl Chloride to trans-Chlorocarbonylbis(dimethylphenylphosphine)iridium(I), 1973, 51, 4145-4151, {{DOI|10.1139/CJC-51-24-4145}}.</ref>
Also when comparing the acidity of HPR<sub>3</sub> (PR<sub>3</sub> = PMe<sub>2</sub>Ph, PPh<sub>3</sub>, PEt<sub>3</sub>) in CD<sub>2</sub>Cl<sub>2</sub>, the resulting [[pKa|pK<sub>a</sub>]] value is the following: [HPMe<sub>2</sub>Ph]<sup>+</sup>= 6.8, [HPPh<sub>3</sub>]<sup>+</sup> = 2.7, [HPEt<sub>3</sub>]<sup>+</sup> = 8.7.<ref>Russell C; Bush and Robert J. Angelici. Inorg. Chem, Phosphine Basicities As Determined by Enthalpies of Protonation 1988, 27, 681-686. {{doi|10.1021/ic00277a022}}</ref><ref>Tianshu Li ; Alan J.; Robert H., ''Chemistry- A European Journal'', An Acidity scale of Tetrafluoroborate Salts of Phosphonium and Iron Hydride compounds in [D2]Dichloromethane, 2007, volume 13, 3796-3803, {{DOI| 10.1002/chem..200601484}}.</ref> Thus PMe2Ph is intermediate in basicity relative to PPh<sub>3</sub> and PEt<sub>3</sub>.
 
The ligand [[cone angle]] (θ) is the apex angle of a cylindrical cone, which is centered 2.28 Å from the center of the P atom. However, the cone angle of an unsymmetrical ligand cannot be determined in the same. In order to determine an effective cone angle for an unsymmetrical ligand PX<sub>1</sub>X<sub>2</sub>X<sub>3</sub>, the following equation is used:
 
:<math>\theta = \frac{2}{3}\sum_{i=1}^3 \frac{\theta_i}2</math>
 
Where θ<sub>i</sub> represent the half angle.
 
The resulting angles for -PMe<sub>3</sub>, PMe<sub>2</sub>Ph, PPh<sub>3</sub> are the following:
PMe<sub>3</sub>= 118°, PMe<sub>2</sub>Ph= 122°, PPh<sub>3</sub>= 145°. Thus PMe<sub>2</sub>Ph is intermediate in size relative to PMe<sub>3</sub> and PPh<sub>3</sub>.<ref>C.A.Tolman, ''Chem.Rev''., Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis., 1977, 313-348, {{DOI|10.1021/cr60307a002}}</ref>
 
==References==
{{Reflist}}
 
[[Category:Tertiary phosphines]]
[[Category:Aromatic compounds]]

Latest revision as of 10:10, 24 November 2014


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