Synthesis of a lariat ether having a phosphinic acid functional group and the crystal structure of its Na/sup +/ complex: Sodium sym-((dibenzo-14-crown-4-oxy)methyl)phenylphosphinate dihydrate diethanolate

Journal Article · Wed May 18 00:00:00 EDT 1988 · Inorg. Chem.; (United States)

DOI:https://doi.org/10.1021/ic00283a023· OSTI ID:5708641

Sachleben, R A; Burns, J H; Brown, G M

A dibenzo-14-crown-4 ether with a pendant arm carrying a phosphinic acid moiety was synthesized and the crystal structure of its sodium salt determined by x-ray diffraction methods. The V-shaped macrocycle is almost identical with the unsubstituted version and has its four ether O atoms oriented to one side in a plane. The Na/sup +/ ion is bonded to these atoms and is 1.5 /angstrom/ above the plane; it is also bonded to the O atom of the oxymethyl side arm and to the O atoms of one water and one ethanol molecule. The phosphinate anion does not coordinate directly to the Na/sup +/ ion but is attached indirectly through an intermediate H/sub 2/O molecule. A hydrogen bonding network joins the complex molecules into dimers that interact with each other in the crystal only through van der Walls contacts. The acid and the salt were also characterized by ir and NMR spectroscopy, and the pK/sub a/ was determined to be 4.5 in 80% methanol-water. Crystallographic data for NaPC/sub 29/H/sub 42/O/sub 11/: monoclinic, a = 18.439 (2) /angstrom/, b = 8.680 (1) /angstrom/, c = 20.606 (1) /angstrom/, /beta/ = 102.95 (1)/degree/, space group P2/sub 1//n, Z = 4. 28 refs., 2 figs., 5 tabs.

• Research Organization: Oak Ridge National Lab., TN (USA)
• DOE Contract Number: AC05-84OR21400
• OSTI ID: 5708641
• Journal Information: Inorg. Chem.; (United States), Vol. 27:10
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
PHOSPHINIC ACID ESTERS
CRYSTAL STRUCTURE
SYNTHESIS
POLYETHYLENE GLYCOLS
SODIUM COMPLEXES
EXPERIMENTAL DATA
ALCOHOLS
ALKALI METAL COMPLEXES
COMPLEXES
DATA
ESTERS
GLYCOLS
HYDROXY COMPOUNDS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANIC POLYMERS
POLYMERS
400201* - Chemical & Physicochemical Properties