15-Crown-5

changed 477209069 15-crown-5 skeletal.svg skin-invert 150 correct ?? Skeletal formula 15-Crown-5-3D-balls.png bg-transparent 170 Ball-and-stick model 1,4,7,10,13-Pentaoxacyclopentadecane 15-crown-5 - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/36336 PubChem Compound National Center for Biotechnology Information 11 October 2011 USA 16 September 2004 Identification and Related Records 33100-27-5 correct CAS correct FDA 7G6K9SB27Y 36336 33416 correct chemspider 251-379-6 15-Crown-5 32401 correct EBI 156289 correct EBI SB0200000 1618144 3897 C1COCCOCCOCCOCCO1 1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2 correct chemspider 1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2 VFTFKUDGYRBSAL-UHFFFAOYSA-N correct chemspider VFTFKUDGYRBSAL-UHFFFAOYAH 10 20 5 colorless liquid 1.113 g cm−3 (at 20 °C) 93-96 at 0.05 mmHg −0.639 1.465 −881.1 to −877.1 kJ mol−1 −5.9157 to −5.9129 MJ mol−1 msds.chem.ox.ac.uk exclamation mark WARNING 302 315 319 305+351+338 1 2 0 113 15-Crown-5 is a crown ether with the formula (C2H4O)5. It is a cyclic pentamer of ethylene oxide. It forms a complex with various cations, including sodium (Na+) https://www.jstage.jst.go.jp/browse/bcsj/61/3/_contents Takeda, Y. A Conductance Study of 1:1 Complexes of 15-Crown-5, 16-Crown-5, and Benzo-15-crown-5 with Alkali Metal Ions in Nonaqueous Solvents Bulletin of the Chemical Society of Japan 1988 61 3 627–632 10.1246/bcsj.61.627 etal free 2019-04-28 2014-01-30 https://web.archive.org/web/20190428042051/https://www.jstage.jst.go.jp/browse/bcsj/61/3/_contents dead and potassium (K+);https://www.rsc.org/publishing/journals/CC/article.asp?doi=b512677k Chen, Chun-Yen Potassium ion recognition by 15-crown-5 functionalized CdSe/ZnS quantum dots in H2O Chem. Comm. 2006 263–265 10.1039/B512677K 3 16391728 etal subscription with a preference for the former. Synthesis 15-Crown-5 can be synthesized using a modified Williamson ether synthesis:Cook Fred L. Caruso Thomas C. Byrne Michael P. Bowers Chauncey W. Speck Don H. Liotta Charles L. 1974 Facile syntheses of 12-crown-4 and 15-crown-5 Tetrahedron Letters en 15 46 4029–4032 10.1016/S0040-4039(01)92075-1 (CH2OCH2CH2Cl)2 + O(CH2CH2OH)2 + 2 NaOH → (CH2CH2O)5 + 2 NaCl + 2 H2O It also forms from the cyclic oligomerization of ethylene oxide in the presence of gaseous boron trifluoride.Liotta Charles L. 15-Crown-5 2001 Encyclopedia of Reagents for Organic Synthesis Chichester, UK John Wiley & Sons, Ltd en 10.1002/047084289x.rc263 978-0-471-93623-7 Berkner Joachim Properties Analogous to 18-crown-6, 15-crown-5 binds to sodium ions. Thus, when treated with this complexing agent, sodium salts often become soluble in organic solvents. First-row transition metal dications fit snugly inside the cavity of 15-crown-5. They are too small to be included in 18-crown-6. The binding of transition metal cations results in multiple hydrogen-bonded interactions from both equatorial and axial aqua ligands, such that highly crystalline solid-state supramolecular polymers can be isolated. Metal salts isolated in this form include Co(ClO4)2, Ni(ClO4)2, Cu(ClO4)2, and Zn(ClO4)2. Seven coordinate species are most common for transition metal complexes of 15-crown-5, with the crown ether occupying the equatorial plane, along with 2 axial aqua ligands. Supramolecular Chemistry, 2nd edition Jonathan W. Steed Jerry L. Atwood Wiley 2009 978-0-470-51233-3 thumb|left|150px|The structure of the complex [Co(15-crown-5)(H2O)2]2+. 15-crown-5 has also been used to isolate salts of oxonium ions. For example, from a solution of tetrachloroauric acid, the oxonium ion [H7O3]+ has been isolated as the salt [(H7O3)(15-crown-5)2][AuCl4]. Neutron diffraction studies revealed a sandwich structure, which shows a chain of water with remarkably long O-H bond (1.12 Å) in the acidic proton, but with a very short OH•••O distance (1.32 Å). thumb|left|150px|Structure of [(H7O3)(15-crown-5)2]+ ion A derivative of 15-crown-5, benzo-15-crown-5, has been used to produce anionic complexes of carbido ligands as their [K(benzo-15-crown-5)2]+ salts: (Ar2N)3MoCH + KCH2Ph + 2 (15-crown-5) → [K(15-crown-5)2]+[(Ar2N)3MoC]− + CH3Ph In 2026, a study demonstrated that 15-crown-5 can act as a structural matrix to isolate otherwise unstable molecular forms. Specifically, within a 15-crown-5 hydroxylaminosolvate crystal structure, molecules of hydroxylamine were successfully trapped and observed for the first time as a stable cyclic dimer (NH2OH)2.Navasardyan M. A. Chernyavskiy D. R. Vener M. V. Crystal structures of hydroxylamine and a 15-crown-5 hydroxylaminosolvate: first observation of a cyclic hydroxylamine dimer (NH2OH)2 CrystEngComm 2026 28 27 4070–4076 10.1039/D6CE00321D See also Host guest chemistry Phase transfer catalyst References Further reading https://infoscience.epfl.ch/record/52153 Klok, H.A. Novel benzo-15-crown-5 functionalized α-olefin/CO terpolymers for membrane applications Macromolecular Chemistry and Physics 1997 198 9 2759–2768 10.1002/macp.1997.021980908 etal subscription https://www.arkat-usa.org/get-file/19080/ Fedorova, O.A. Facile synthesis of novel styryl ligands containing a 15-crown-5 ether moiety Arkivoc 2005 xv 12–24 10.3998/ark.5550190.0006.f03 etal free 2027/spo.5550190.0006.f03 free External links www.ChemBlink.com Category:Crown ethers