Synthesis and Molecular Structures of the Lowest Melting Odd- and Even-Numbered α,β-Unsaturated Carboxylic Acids—(E)-Hept-2-Enoic Acid and (E)-Oct-2-Enoic Acid

Sonneck, Marcel; Spannenberg, Anke; Wohlrab, Sebastian; Peppel, Tim

doi:10.3390/cryst6060066

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“…As part of ongoing efforts to synthesize feasible new ligands for these Cu-based complexes (Sonneck et al, 2015(Sonneck et al, , 2016, the title compound was obtained as a side product in the attempted synthesis of the precursor compound (E)-1-phenylpent-2-en-1-one in moderate yield (30%).…”

Section: Structure Descriptionmentioning

confidence: 99%

3-Ethylindan-1-one

et al. 2017

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The title compound, C 11 H 12 O, has been prepared as a side product in the attempted room-temperature synthesis of (E)-1-phenylpent-2-en-1-one. The molecular structure consists of an approximately planar indanone core (r.m.s. deviation = 0.042 Å ) with the ethyl group protruding from this plane. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of C-HÁ Á ÁO hydrogen bonds, forming rings of R 2 2 (10) graph-set motif. The dimers are further connected by C-HÁ Á Á interactions into chains running parallel to [101]. Structure descriptionIn recent years, new Cu-based complexes suitable for the photocatalytic water-splitting reaction have attracted increasing attention due to their application in sustainable hydrogen-storage technologies (Chen et al., 2017). As part of ongoing efforts to synthesize feasible new ligands for these Cu-based complexes (Sonneck et al., 2015(Sonneck et al., , 2016, the title compound was obtained as a side product in the attempted synthesis of the precursor compound (E)-1-phenylpent-2-en-1-one in moderate yield (30%).The title compound 3-ethylindan-1-one is a racemic ring-closure product of (E)-1-phenylpent-2-en-1-one and the asymmetric unit consists of one indanone molecule (Fig. 1). The indanone ring system is nearly planar [r.m.s. deviation = 0.042 Å ; maximum displacement 0.1082 (12) Å for atom C2] with the ethyl group protruding from this plane. All bond lengths and angles are in expected ranges and the C O bond equals 1.2138 (13) Å . The structure exhibits a typical geometry that corresponds well with that of the parent structure 1-indanone (Morin et al., 1974;Peñ a Ruiz et al., 2004).In the crystal structure, centrosymmetric molecules are linked into dimers through pairs of C-HÁ Á ÁO hydrogen bonds (Table 1), forming rings of R 2 2 (10) graph-set motif. The dimers are further connected by C-HÁ Á Á interactions, forming chains parallel to [101].

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Section: Structure Descriptionmentioning

confidence: 99%