Synthesis and structural characterisation of 1'-(diphenylphosphino) ferrocene-1-phosphonic acid, its ammonium salts and Pd(II) complexes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F19%3A10394082" target="_blank" >RIV/00216208:11310/19:10394082 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=LDoqMWDoaS" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=LDoqMWDoaS</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jorganchem.2019.04.012" target="_blank" >10.1016/j.jorganchem.2019.04.012</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and structural characterisation of 1'-(diphenylphosphino) ferrocene-1-phosphonic acid, its ammonium salts and Pd(II) complexes

Popis výsledku v původním jazyce

A new polar phosphinoferrocene ligand, viz. 1&apos;-(diphenylphosphino)ferrocene-1-phosphonic acid (H2L), was prepared by hydrolysis of the corresponding phosphonate ethyl ester. However, the compound is relatively unstable, gradually decomposing upon prolonged storage, ultimately affording phosphine oxide H2LO. When the phosphine moiety was protected (e.g., in phosphine oxide H2LO and adduct H2L center dot BH3), no decomposition was observed. An alternative approach to prepare more stable H2L surrogates by converting the phosphonic acid into ammonium salts (dabcoH)(HL) and [(OHCH2CH2)(2)NH2](HL) (dabco = 1,4-diazabicyclo[2.2.2]octane) resulted in no significant stabilisation. H2L reacted with [PdCl2(cod)] (cod = cycloocta-1,5-diene), producing the bis(phosphine) complex, trans-[PdCl2(H2L-kappa P)(2)]. When mixed with Pd(II)-acetylacetonate (acac) complexes with ortho-metallated auxiliary ligands, [(L-CY)Pd(acac)] (L-CY = 2-[(dimethylamino-kappa N)methyl]phenyl-kappa C-1 and 2-[(methylthio-kappa S)methyl]phenyl-kappa C-1), H2L gave rise to bis-chelate complexes of the [(L-CY)Pd(HL-kappa O-2,P)] type. H2L, the ammonium salts featuring the HL- anion, and all Pd(II) complexes were structurally characterised by single-crystal X-ray diffraction analysis. Variations in phosphonate P-O bond lengths observed in the crystal structures were rationalised by DFT computations.

Název v anglickém jazyce

Synthesis and structural characterisation of 1'-(diphenylphosphino) ferrocene-1-phosphonic acid, its ammonium salts and Pd(II) complexes

Popis výsledku anglicky

A new polar phosphinoferrocene ligand, viz. 1&apos;-(diphenylphosphino)ferrocene-1-phosphonic acid (H2L), was prepared by hydrolysis of the corresponding phosphonate ethyl ester. However, the compound is relatively unstable, gradually decomposing upon prolonged storage, ultimately affording phosphine oxide H2LO. When the phosphine moiety was protected (e.g., in phosphine oxide H2LO and adduct H2L center dot BH3), no decomposition was observed. An alternative approach to prepare more stable H2L surrogates by converting the phosphonic acid into ammonium salts (dabcoH)(HL) and [(OHCH2CH2)(2)NH2](HL) (dabco = 1,4-diazabicyclo[2.2.2]octane) resulted in no significant stabilisation. H2L reacted with [PdCl2(cod)] (cod = cycloocta-1,5-diene), producing the bis(phosphine) complex, trans-[PdCl2(H2L-kappa P)(2)]. When mixed with Pd(II)-acetylacetonate (acac) complexes with ortho-metallated auxiliary ligands, [(L-CY)Pd(acac)] (L-CY = 2-[(dimethylamino-kappa N)methyl]phenyl-kappa C-1 and 2-[(methylthio-kappa S)methyl]phenyl-kappa C-1), H2L gave rise to bis-chelate complexes of the [(L-CY)Pd(HL-kappa O-2,P)] type. H2L, the ammonium salts featuring the HL- anion, and all Pd(II) complexes were structurally characterised by single-crystal X-ray diffraction analysis. Variations in phosphonate P-O bond lengths observed in the crystal structures were rationalised by DFT computations.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organometallic Chemistry

ISSN

0022-328X

e-ISSN

—

Svazek periodika

891

Číslo periodika v rámci svazku

August

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

10

Strana od-do

44-53

Kód UT WoS článku

000466789300007

EID výsledku v databázi Scopus

2-s2.0-85064543532