Crystal structure of 4-(prop-2-yn-1-yloxy)benzonitrile

Kanagawa, Mayu; Okuno, Tsunehisa

doi:10.1107/s2056989014028035

Cited by 2 publications

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References 15 publications

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“…All chemicals were purchased from Kanto Chemical Co. Ltd. or Sigma Aldrich Co. Ltd. and used without further purification. 9-Ethynyl-9H-carbazole [29], 4-(2-propynyloxy)nitrobenzene and 4-(2-propynyloxy)benzonitrile [30] were prepared according to the reported methods.…”

Section: -2 Materialsmentioning

confidence: 99%

Conformational polymorphs and solid-state polymerization of 9-(1,3-butadiynyl)carbazole derivatives

Tabata

Kuwamoto

Okuno

2016

Journal of Molecular Structure

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The novel diacetylenes, 9-(5-(4-nitrophenoxy)penta-1,3-diyn-1-yl)-9H-carbazole (1) and 4-((5-(9H-carbazol-9-yl)penta-2,4-diyn-1-yl)oxy)benzonitrile (2), were prepared and characterized by crystallographic analyses. Compound 1 gave two conformational polymorphs, 1-(I) and 1-(II), whose differences were concluded to originate in intermolecular interactions among nitrophenyl groups. Crystal 1-(I) and 2 had suitable molecular arrangements for solid-state polymerization and polymerized by thermal annealing to give crystalline polydiacetylenes (PDAs). While an arrangement of 1-(II) was unsuitable for the polymerization. The PDAs showed broad absorption from UV to

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Section: -2 Materialsmentioning

confidence: 99%

Conformational polymorphs and solid-state polymerization of 9-(1,3-butadiynyl)carbazole derivatives

Tabata

Kuwamoto

Okuno

2016

Journal of Molecular Structure

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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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Crystal structure of 4-(prop-2-yn-1-yloxy)benzonitrile

Cited by 2 publications

References 15 publications

Conformational polymorphs and solid-state polymerization of 9-(1,3-butadiynyl)carbazole derivatives

Conformational polymorphs and solid-state polymerization of 9-(1,3-butadiynyl)carbazole derivatives

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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