Diphenylzinc: Difference between revisions
Appearance
Content deleted Content added
m r2.7.1) (robot Adding: zh:二苯基锌 |
m convert special characters (via WP:JWB) |
||
(17 intermediate revisions by 14 users not shown) | |||
Line 1: | Line 1: | ||
{{Chembox |
{{Chembox |
||
| Verifiedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = 426807310 |
||
| ImageFile = diphenylzinc.svg |
| ImageFile = diphenylzinc.svg |
||
| |
| ImageSize = 220px |
||
| |
| ImageAlt = Skeletal formula of diphenylzinc monomer |
||
| ImageFile1 = Diphenylzinc 3D ball.png |
|||
| ImageSize1 = 220px |
|||
| ImageAlt1 = Ball-and-stick model of the diphenylzinc monomer molecule |
|||
| IUPACName = |
| IUPACName = |
||
| PIN = |
| PIN = |
||
| OtherNames = |
| OtherNames = |
||
| |
|Section1={{Chembox Identifiers |
||
| CASNo_Ref = {{cascite|correct|??}} |
|||
| |
| CASNo = 1078-58-6 |
||
| |
| PubChem = 517896 |
||
⚫ | |||
| EC_number = 214-082-2 |
|||
⚫ | |||
| ChEBI = 51499 |
|||
⚫ | |||
| Beilstein = 3603125 |
|||
⚫ | |||
| |
| Gmelin = 28161 |
||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|||
⚫ | |||
| ChemSpiderID = 10395624 |
|||
⚫ | |||
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|||
⚫ | |||
| StdInChI = 1S/2C6H5.Zn/c2*1-2-4-6-5-3-1;/h2*1-5H; |
|||
⚫ | |||
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|||
⚫ | |||
| StdInChIKey = MKRVHLWAVKJBFN-UHFFFAOYSA-N |
|||
⚫ | |||
⚫ | |||
| Autoignition = }} |
|||
⚫ | |||
⚫ | |||
⚫ | |||
| Density = |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| GHSPictograms = {{GHS02}} |
|||
| GHSSignalWord = Danger |
|||
| HPhrases = {{H-phrases|228|250}} |
|||
| PPhrases = {{P-phrases|210|222|240|241|280|302+334|370+378|422}} |
|||
⚫ | |||
⚫ | |||
| AutoignitionPt = }} |
|||
}} |
}} |
||
'''Diphenylzinc''' is an [[organozinc compound]]. It is commonly used as the synthetic equivalent of |
'''Diphenylzinc''' is an [[organozinc compound]]. It is commonly used as the synthetic equivalent of a Ph<sup>−</sup> [[synthon]]. Solvent-free diphenylzinc exists as dimeric {{Nowrap|PhZn(μ-Ph)<sub>2</sub>ZnPh}} molecules in the solid state.<ref>{{cite journal | last1 = Markies | first1 = Peter R. | last2 = Schat | first2 = Gerrit | last3 = Akkerman | first3 = Otto S. | last4 = Bickelhaupt | first4 = Friedrich | last5 = Smeets | first5 = Wilberth J. J. | last6 = Spek | first6 = Anthony L. | title = Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc | doi = 10.1021/om00158a022 | year = 1990 | pages = 2243 | volume = 9 | journal = [[Organometallics]] | issue = 8}}</ref> |
||
{{Multiple image |
|||
⚫ | |||
| align = left |
|||
| width = 150 |
|||
| image1 = Diphenylzinc dimer.svg |
|||
| alt1 = Skeletal formula of diphenylzinc dimer |
|||
| image2 = Diphenylzinc dimer 3D ball.png |
|||
| alt2 = Ball-and-stick model of the diphenylzinc dimer molecule |
|||
⚫ | |||
}} |
|||
{{clear left}} |
|||
Diphenylzinc is commercially available. It may be prepared by reaction of [[phenyllithium]] with [[zinc bromide]]:<ref>{{cite journal | last1 = Curtin | first1 = David Y. | last2 = Tveten | first2 = John L. | journal = [[J. Org. Chem.]] | title = Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds | |
Diphenylzinc is commercially available. It may be prepared by reaction of [[phenyllithium]] with [[zinc bromide]]:<ref>{{cite journal | last1 = Curtin | first1 = David Y. | last2 = Tveten | first2 = John L. | journal = [[J. Org. Chem.]] | title = Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds | |
||
volume = 26 | pages = 1764 | year = 1961 | doi = 10.1021/jo01065a017}}</ref> |
volume = 26 | pages = 1764 | year = 1961 | doi = 10.1021/jo01065a017 | issue = 6}}</ref> |
||
:2 PhLi + ZnBr<sub>2</sub> |
:2 PhLi + ZnBr<sub>2</sub> → Ph<sub>2</sub>Zn + 2 LiBr |
||
It may also be prepared by the reaction of [[diphenylmercury]] with zinc metal.<ref name = markies>{{cite journal | last1 = Markies | first1 = P | doi = 10.1016/0022-328X(92)80090-K | title = Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph<sub>2</sub>Zn·glyme and Ph<sub>2</sub>Zn·diglyme | year = 1992 | pages = |
It may also be prepared by the reaction of [[phenylmagnesium bromide]] with [[zinc chloride]] or [[diphenylmercury]] with zinc metal.<ref name = markies>{{cite journal | last1 = Markies | first1 = P | doi = 10.1016/0022-328X(92)80090-K | title = Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph<sub>2</sub>Zn·glyme and Ph<sub>2</sub>Zn·diglyme | year = 1992 | pages = 1–13 | volume = 430 | journal = [[J. Organomet. Chem.]] | last2 = Schat | first2 = Gerrit | last3 = Akkerman | first3 = Otto S. | last4 = Bickelhaupt | first4 = F. | last5 = Spek | first5 = Anthony L.}}</ref><ref>{{Citation|last=Pelletier|first=Guillaume|title=Diphenylzinc|date=2013|encyclopedia=[[Encyclopedia of Reagents for Organic Synthesis]]|place=Chichester, UK|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289x.rn01548|isbn=978-0-471-93623-7}}</ref> |
||
==References== |
==References== |
||
{{reflist}} |
{{reflist}} |
||
{{Zinc compounds}} |
|||
[[Category:Organozinc compounds]] |
[[Category:Organozinc compounds]] |
||
[[Category:Phenyl compounds]] |
|||
[[zh:二苯基锌]] |