Centrosymmetric structures of three substituted malonic acids

Jerry Joe Ebow Kingsley Harrison, Robert Kingsford-Adaboh, Syunsuke Ueda, Kazuma Gotoh, Hiroyuki Ishida

Research output: Contribution to journalArticle

Abstract

Crystal structures of 2-methylmalonic acid, 2-ethylmalonic acid and 2-phenylmalonic acid, which are derivatives of malonic acid and have found usefulness in diagnostics and biochemical evaluations as markers and organic synthesis, are reported. 2-Methylmalonic acid and 2-ethylmalonic acid both crystallize in triclinic P-1 space group with cell parameters of a = 5.1033(7), b = 5.4231(7), c = 10.0887(14) Å, α = 88.074(4), β = 89.999(5) and γ = 67.955(4)° for 2-methylmalonic acid, and a = 5.2073(4), b = 7.2258(6), c = 8.5655(6) Å, α = 88.086(2), β = 75.307(2) and γ = 85.904(3)° for 2-ethylmalonic acid, 2-phenylmalonic acid on the other hand crystallizes in monoclinic P21/c with cell parameters a = 8.6494(4), b = 5.48733(19), c = 17.1706(6) Å and β = 90.1068(17)°. The observed topology of the hydrogen bonding network is to a large extent dictated by the symmetrical substitution pattern with an open arrangement of hydrogen bonds. Each of the C=O double bonds in both 2-methylmalonic acid and 2-ethylmalonic acid is translationally offset, forming planar centrosymmetric carboxy-dimers. Molecules related by centre of inversion in spite of the constraints imposed by substituents are linked by O-H⋯O hydrogen bonds. This results in the formation of parallel zig-zag chains running along the [101] direction. In 2-phenylmalonic acid, the zig-zag molecular residue is parallely stacked with successive catemers. These laterally displaced catemers are also coiled in a twofold twist on the screw axis (x, 1/2 + y, 1/2 - z) along the b-glide (x, 1/2 - y, 1/2 + z) when viewed along the (101) plane.

Original languageEnglish
Pages (from-to)306-311
Number of pages6
JournalJournal of Chemical Crystallography
Volume41
Issue number3
DOIs
Publication statusPublished - Mar 2011

Fingerprint

Methylmalonic Acid
Hydrogen bonds
acids
Dimers
Substitution reactions
Crystal structure
Topology
Derivatives
Molecules
malonic acid
ethylmalonic acid
hydrogen bonds
phenylmalonic acid
screws
cells
markers

Keywords

  • 2-Ethylmalonic acid
  • 2-Methylmalonic acid
  • 2-Phenylmalonic acid
  • Biochemical markers
  • Catemer
  • Centrosymmetric dimers
  • Hydrogen bonding

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Centrosymmetric structures of three substituted malonic acids. / Harrison, Jerry Joe Ebow Kingsley; Kingsford-Adaboh, Robert; Ueda, Syunsuke; Gotoh, Kazuma; Ishida, Hiroyuki.

In: Journal of Chemical Crystallography, Vol. 41, No. 3, 03.2011, p. 306-311.

Research output: Contribution to journalArticle

Harrison, Jerry Joe Ebow Kingsley ; Kingsford-Adaboh, Robert ; Ueda, Syunsuke ; Gotoh, Kazuma ; Ishida, Hiroyuki. / Centrosymmetric structures of three substituted malonic acids. In: Journal of Chemical Crystallography. 2011 ; Vol. 41, No. 3. pp. 306-311.
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abstract = "Crystal structures of 2-methylmalonic acid, 2-ethylmalonic acid and 2-phenylmalonic acid, which are derivatives of malonic acid and have found usefulness in diagnostics and biochemical evaluations as markers and organic synthesis, are reported. 2-Methylmalonic acid and 2-ethylmalonic acid both crystallize in triclinic P-1 space group with cell parameters of a = 5.1033(7), b = 5.4231(7), c = 10.0887(14) {\AA}, α = 88.074(4), β = 89.999(5) and γ = 67.955(4)° for 2-methylmalonic acid, and a = 5.2073(4), b = 7.2258(6), c = 8.5655(6) {\AA}, α = 88.086(2), β = 75.307(2) and γ = 85.904(3)° for 2-ethylmalonic acid, 2-phenylmalonic acid on the other hand crystallizes in monoclinic P21/c with cell parameters a = 8.6494(4), b = 5.48733(19), c = 17.1706(6) {\AA} and β = 90.1068(17)°. The observed topology of the hydrogen bonding network is to a large extent dictated by the symmetrical substitution pattern with an open arrangement of hydrogen bonds. Each of the C=O double bonds in both 2-methylmalonic acid and 2-ethylmalonic acid is translationally offset, forming planar centrosymmetric carboxy-dimers. Molecules related by centre of inversion in spite of the constraints imposed by substituents are linked by O-H⋯O hydrogen bonds. This results in the formation of parallel zig-zag chains running along the [101] direction. In 2-phenylmalonic acid, the zig-zag molecular residue is parallely stacked with successive catemers. These laterally displaced catemers are also coiled in a twofold twist on the screw axis (x, 1/2 + y, 1/2 - z) along the b-glide (x, 1/2 - y, 1/2 + z) when viewed along the (101) plane.",
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AU - Kingsford-Adaboh, Robert

AU - Ueda, Syunsuke

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2011/3

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N2 - Crystal structures of 2-methylmalonic acid, 2-ethylmalonic acid and 2-phenylmalonic acid, which are derivatives of malonic acid and have found usefulness in diagnostics and biochemical evaluations as markers and organic synthesis, are reported. 2-Methylmalonic acid and 2-ethylmalonic acid both crystallize in triclinic P-1 space group with cell parameters of a = 5.1033(7), b = 5.4231(7), c = 10.0887(14) Å, α = 88.074(4), β = 89.999(5) and γ = 67.955(4)° for 2-methylmalonic acid, and a = 5.2073(4), b = 7.2258(6), c = 8.5655(6) Å, α = 88.086(2), β = 75.307(2) and γ = 85.904(3)° for 2-ethylmalonic acid, 2-phenylmalonic acid on the other hand crystallizes in monoclinic P21/c with cell parameters a = 8.6494(4), b = 5.48733(19), c = 17.1706(6) Å and β = 90.1068(17)°. The observed topology of the hydrogen bonding network is to a large extent dictated by the symmetrical substitution pattern with an open arrangement of hydrogen bonds. Each of the C=O double bonds in both 2-methylmalonic acid and 2-ethylmalonic acid is translationally offset, forming planar centrosymmetric carboxy-dimers. Molecules related by centre of inversion in spite of the constraints imposed by substituents are linked by O-H⋯O hydrogen bonds. This results in the formation of parallel zig-zag chains running along the [101] direction. In 2-phenylmalonic acid, the zig-zag molecular residue is parallely stacked with successive catemers. These laterally displaced catemers are also coiled in a twofold twist on the screw axis (x, 1/2 + y, 1/2 - z) along the b-glide (x, 1/2 - y, 1/2 + z) when viewed along the (101) plane.

AB - Crystal structures of 2-methylmalonic acid, 2-ethylmalonic acid and 2-phenylmalonic acid, which are derivatives of malonic acid and have found usefulness in diagnostics and biochemical evaluations as markers and organic synthesis, are reported. 2-Methylmalonic acid and 2-ethylmalonic acid both crystallize in triclinic P-1 space group with cell parameters of a = 5.1033(7), b = 5.4231(7), c = 10.0887(14) Å, α = 88.074(4), β = 89.999(5) and γ = 67.955(4)° for 2-methylmalonic acid, and a = 5.2073(4), b = 7.2258(6), c = 8.5655(6) Å, α = 88.086(2), β = 75.307(2) and γ = 85.904(3)° for 2-ethylmalonic acid, 2-phenylmalonic acid on the other hand crystallizes in monoclinic P21/c with cell parameters a = 8.6494(4), b = 5.48733(19), c = 17.1706(6) Å and β = 90.1068(17)°. The observed topology of the hydrogen bonding network is to a large extent dictated by the symmetrical substitution pattern with an open arrangement of hydrogen bonds. Each of the C=O double bonds in both 2-methylmalonic acid and 2-ethylmalonic acid is translationally offset, forming planar centrosymmetric carboxy-dimers. Molecules related by centre of inversion in spite of the constraints imposed by substituents are linked by O-H⋯O hydrogen bonds. This results in the formation of parallel zig-zag chains running along the [101] direction. In 2-phenylmalonic acid, the zig-zag molecular residue is parallely stacked with successive catemers. These laterally displaced catemers are also coiled in a twofold twist on the screw axis (x, 1/2 + y, 1/2 - z) along the b-glide (x, 1/2 - y, 1/2 + z) when viewed along the (101) plane.

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