Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)

Sausa, Rosario C.; Lastovickova, Dominika N.; La Scala, John J.

doi:10.1107/S2056989018016316

Title: Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)

Abstract

The title compounds 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde), C₁₇H₁₆O₄, (1), and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde), C₁₉H₁₆O₆, (2), crystallize with one molecule in the asymmetric unit. In molecule (1), a >C(CH₃)₂group bridges two nearly planar salicylaldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Molecule (1) exhibits a bridge angle of 109.5 (2)° with the salicylaldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, molecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both molecules exhibit two intramolecular O—H...O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O—H...O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related molecule form a chain along [10\overline{1}]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation.

Authors:

Sausa, Rosario C. ^[1]; Lastovickova, Dominika N. ^[2]; La Scala, John J. ^[3]

US Army Research Laboratory, RDRL-WML-B, Aberdeen Proving Ground, MD (United States)
US Army Research Laboratory, RDRL-WML-G, Aberdeen Proving Ground, MD (United States). Also an ORISE Postdoctoral Research Fellow
US Army Research Laboratory, RDRL-WML-G, Aberdeen Proving Ground, MD (United States)

Publication Date:: Thu Nov 22 00:00:00 EST 2018

Research Org.:: Oak Ridge Inst. for Science and Education (ORISE), Oak Ridge, TN (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1630006

Grant/Contract Number:: SC0014664

Resource Type:: Accepted Manuscript

Journal Name:: Acta Crystallographica. Section E, Crystallographic Communications

Additional Journal Information:: Journal Volume: 74; Journal Issue: 12; Journal ID: ISSN 2056-9890

Publisher:: International Union of Crystallography

Country of Publication:: United States

Language:: English

Citation Formats


                    Sausa, Rosario C., Lastovickova, Dominika N., and La Scala, John J. Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde).  United States: N. p., 2018. 
Web.  doi:10.1107/S2056989018016316.

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                    Sausa, Rosario C., Lastovickova, Dominika N., & La Scala, John J. Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde).  United States.  https://doi.org/10.1107/S2056989018016316

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                    Sausa, Rosario C., Lastovickova, Dominika N., and La Scala, John J. Thu .  
"Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)".  United States.  https://doi.org/10.1107/S2056989018016316.  https://www.osti.gov/servlets/purl/1630006.

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@article{osti_1630006,

  title        = {Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)},

  author       = {Sausa, Rosario C. and Lastovickova, Dominika N. and La Scala, John J.},

  abstractNote = {The title compounds 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde), C17H16O4, (1), and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde), C19H16O6, (2), crystallize with one molecule in the asymmetric unit. In molecule (1), a >C(CH3)2group bridges two nearly planar salicylaldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Molecule (1) exhibits a bridge angle of 109.5 (2)° with the salicylaldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, molecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both molecules exhibit two intramolecular O—H...O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O—H...O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related molecule form a chain along [10\overline{1}]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation.},

  doi          = {10.1107/S2056989018016316},

  journal      = {Acta Crystallographica. Section E, Crystallographic Communications},

  number       = 12,

  volume       = 74,

  place        = {United States},

  year         = {Thu Nov 22 00:00:00 EST 2018},

  month        = {Thu Nov 22 00:00:00 EST 2018}

}

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Title: Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)

Abstract

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