Synthesis of mono and doubly alkynyl substituted ferrocene and its crystal engineering using –C–H···O supramolecular synthon

Thakur, Arunabha; Adarsh, N. N.; Chakraborty, Arpan; Devi, M. Suseela; Ghosh, Sundargopal

doi:10.1016/j.jorganchem.2009.11.017

Cited by 22 publications

(16 citation statements)

References 32 publications

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“…A chemical oxidation was then carried out, wherein a dichloromethane solution of 5 was treated with [C 12 H 8 S 2 ][SbCl 6 ] and left overnight at −10 °C, providing bright blue X‐ray‐quality crystals of [ 5 + ][SbCl 6 ]. Perhaps the most relevant aspect of the molecular structure determined by X‐ray analysis (Figure ) is that the acetylenic C≡C bond length of 1.186 Å is essentially unchanged from that reported for neutral 5 , and close to that reported for the ethynyldecamethylferrocenium ion . We note also that the ‐C≡CH stretching frequency, ν C≡CH , measured for 5 + was within experimental error of that of 5 (2121 cm −1 vs 2117 cm −1 , respectively).…”

Section: Resultssupporting

confidence: 73%

Anodic Oxidation of Ethynylferrocene Derivatives in Homogeneous Solution and Following Anodic Deposition onto Glassy Carbon Electrodes

et al. 2019

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Eight ferrocene derivatives linked by either an ether, amine, or phenylacetylene moiety to a terminal ethynyl group were covalently deposited on glassy carbon electrodes by anodic electrochemical methods. The lithio activation method, in which the terminal hydrogen of the ethynyl group is replaced by a lithium atom before anodic oxidation, was successfully employed in all cases. Direct oxidation of the inactivated ethynyl group also resulted in surface deposition. Surface coverages between 1×10−10 mol cm−2 and 14×10−10 mol cm−2 were achieved. Cyclic voltammetry scans of the modified electrodes in pure electrolytes differed depending on the size of the supporting electrolyte anion, as little as half the current being measured for a [B(C6F5)4]− vs. [PF6]− solution, suggesting differences in ion transport near the electrode surface. An ether‐linked ethynylferrocenium ion (5+) was isolated after electrolytic and chemical oxidation of 5 and characterized by X‐Ray crystallography as its [SbCl6]− salt.

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Section: Resultssupporting

confidence: 73%

Anodic Oxidation of Ethynylferrocene Derivatives in Homogeneous Solution and Following Anodic Deposition onto Glassy Carbon Electrodes

et al. 2019

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“…3). Such contacts are often overlooked, but they have been reported previously for both terminal and nonterminal alkyne systems (Banerjee et al, 2006;Thakur et al, 2010;McAdam et al, 2012). Overall, these contacts generate a three-dimensional network with molecules stacked in interconnected columns along the b axis ( Fig.…”

Section: Supramolecular Featuresmentioning

confidence: 80%

Crystal structure of 4-(prop-2-ynyloxy)-2,2,6,6-tetramethylpiperidin-1-oxyl

et al. 2014

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“…(2006) have studied the crystal structures of closely related gem ‐alkynols and identified the occurrence of three synthons depending on the hydrogen bond networks formed between the alcohol and the alkyl groups . Furthermore, the C–H⋅⋅⋅O hydrogen bonds have been identified in related prop‐2‐yn‐1‐yloxy bearing compounds, together with C–H⋅⋅⋅π interactions involving the alkyne group as acceptor …”

Section: Resultsmentioning

confidence: 99%

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

et al. 2019

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The 2-(prop-2-yn-1-yloxy)naphthalene (compound I) and 1nitro-2-(prop-2-yn-1-yloxy)benzene (compound II) were prepared in excellent yields by the reaction of propargyl bromide with 2-naphthol and 2-nitrophenol, respectively. Structural and conformational properties of both compounds have been analyzed using a combined approach including single-crystal X-ray diffraction and quantum chemical calculations. Two forms are found to be stable and nearly isoenergetic conformers, depending on the mutual orientation of the C � C triple bond and the O-C single bond of the prop-2-yn-1-yloxy group. The gauche conformation is the most stable form for the vacuum isolated species, with the anti conformation higher in energy by 1.00 and 1.89 kcal/mol computed at the M06-2X/6-311 + + G(d,p) level of approximation, for I and II, respectively. The gauche form is observed in the crystal of I but the nearly planar anti conformation is adopted in the crystalline phase of compound II. The occurrence of C-H⋅⋅⋅π and C-H⋅⋅⋅O intermolecular interactions involving the acidic -C � C-H hydrogen donor and -C � C-and -OCH 2 -acceptors is discussed. Furthermore, vibrational features of the prop-2-yn-1-yloxy moiety are analyzed by infrared and Raman spectroscopy. The UV-Vis spectrum shows the presence of well-defined absorption at ca. 280 and 320 nm assigned to the π!π* transitions in the naphtyl/benzyl and prop-2-yn-1-yloxy groups, respectively.

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Synthesis of mono and doubly alkynyl substituted ferrocene and its crystal engineering using –C–H···O supramolecular synthon

Cited by 22 publications

References 32 publications

Anodic Oxidation of Ethynylferrocene Derivatives in Homogeneous Solution and Following Anodic Deposition onto Glassy Carbon Electrodes

Anodic Oxidation of Ethynylferrocene Derivatives in Homogeneous Solution and Following Anodic Deposition onto Glassy Carbon Electrodes

Crystal structure of 4-(prop-2-ynyloxy)-2,2,6,6-tetramethylpiperidin-1-oxyl

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

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