6533b854fe1ef96bd12ae0ff
RESEARCH PRODUCT
Crystal structure of ethyl 2-(di-eth-oxy-phosphor-yl)-2-(2,3,4-tri-meth-oxy-phen-yl)acetate.
Dieter SchollmeyerSiegfried R. WaldvogelMoritz Schubertsubject
Steric effectschemistry.chemical_classificationcrystal structureCrystallographyMichaelis–Arbuzov reactionDouble bondChemistryHydrogen bondGeneral ChemistryCrystal structurephosphonoacetateCondensed Matter PhysicsBioinformaticsData ReportsBond lengthCrystalCrystallographyMolecular geometryQD901-999hydrogen bondsMichaelis–Arbuzov reactionGeneral Materials Sciencenon-merohedral twindescription
The title compound, C17H27O8P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-trimethoxyphenyl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of thesp3-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the ethoxy groups connected to the phosphorous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three methoxy groups emerge out of the benzene-ring plane due to steric hindrance [C—C—O—C torsion angles = −179.9 (3)°, −52.9 (4)° and 115.3 (4)°]. In the crystal, inversion dimers linked by pairs of C—H...O=P hydrogen bonds generateR22(14) loops. The chosen crystal was modelled as a non-merohedral twin.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-08-01 | Acta crystallographica. Section E, Structure reports online |