Electron Diffraction Study of the Molecular Structure of 1,3‐Diphenylpropane‐1,2,3‐trione (Diphenyl Triketone)

György Schultz, I. Hargittai, Thomas Doerner, Rolf Gleiter

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The molecular structure of 1,3‐diphenylpropane‐1,2,3‐trione (diphenyl triketone) has been determined by gas‐phase electron diffraction at 130°C nozzle temperature. It has been found that the phenyl rings are nearly coplanar with the adjacent carbonyl groups, and the two Cph–C(O)–C(O)–C(O) dihedral angles are ‐ 129.5 ± 0.8 and ‐ 107.1 ± 0.8° (0° corresponds to the syn form). Bond distances (rg, Å) and bond angles (deg) with estimated total errors are CH 1.105 ± 0.006, O  C 1.213 ± 0.003, < Cph–Cph> 1.404± 0.003, Cph–C(O) 1.478 ± 0.005, C(O)–C(O) 1.558 ± 0.004, Cph–C(O)–C(O) 120.0 ± 0.3, CphC(O)O 120.8 ± 0.4, C(O)–C(O)–C(O) 117.3 ± 0.4, Cph–Cph(CO)–Cph 119.8 ± 0.6. Although there is a general agreement between the gas‐phase and crystal molecular structures there are some notable differences. One of the benzene rings is slightly turned about the Cph–C(O) axis in the opposite direction in the gas molecule as compared to the crystal. This causes a marked shortening of the O… H intramolecular contact (to 2.18 Á) between the central oxygen and an ortho‐hydrogen.

Original languageEnglish
Pages (from-to)1411-1414
Number of pages4
JournalChemische Berichte
Volume124
Issue number6
DOIs
Publication statusPublished - 1991

Fingerprint

Electron diffraction
Molecular structure
Dihedral angle
Carbon Monoxide
Benzene
Nozzles
Crystal structure
Gases
Oxygen
Crystals
Molecules
Temperature
diphenyl
Direction compound

Keywords

  • Conformation
  • Electron diffraction
  • Gas‐crystal structure comparison
  • Propane‐1,2,3‐trione, 1,3‐diphenyl‐

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Electron Diffraction Study of the Molecular Structure of 1,3‐Diphenylpropane‐1,2,3‐trione (Diphenyl Triketone). / Schultz, György; Hargittai, I.; Doerner, Thomas; Gleiter, Rolf.

In: Chemische Berichte, Vol. 124, No. 6, 1991, p. 1411-1414.

Research output: Contribution to journalArticle

Schultz, György ; Hargittai, I. ; Doerner, Thomas ; Gleiter, Rolf. / Electron Diffraction Study of the Molecular Structure of 1,3‐Diphenylpropane‐1,2,3‐trione (Diphenyl Triketone). In: Chemische Berichte. 1991 ; Vol. 124, No. 6. pp. 1411-1414.
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abstract = "The molecular structure of 1,3‐diphenylpropane‐1,2,3‐trione (diphenyl triketone) has been determined by gas‐phase electron diffraction at 130°C nozzle temperature. It has been found that the phenyl rings are nearly coplanar with the adjacent carbonyl groups, and the two Cph–C(O)–C(O)–C(O) dihedral angles are ‐ 129.5 ± 0.8 and ‐ 107.1 ± 0.8° (0° corresponds to the syn form). Bond distances (rg, {\AA}) and bond angles (deg) with estimated total errors are CH 1.105 ± 0.006, O  C 1.213 ± 0.003, < Cph–Cph> 1.404± 0.003, Cph–C(O) 1.478 ± 0.005, C(O)–C(O) 1.558 ± 0.004, Cph–C(O)–C(O) 120.0 ± 0.3, CphC(O)O 120.8 ± 0.4, C(O)–C(O)–C(O) 117.3 ± 0.4, Cph–Cph(CO)–Cph 119.8 ± 0.6. Although there is a general agreement between the gas‐phase and crystal molecular structures there are some notable differences. One of the benzene rings is slightly turned about the Cph–C(O) axis in the opposite direction in the gas molecule as compared to the crystal. This causes a marked shortening of the O… H intramolecular contact (to 2.18 {\'A}) between the central oxygen and an ortho‐hydrogen.",
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T1 - Electron Diffraction Study of the Molecular Structure of 1,3‐Diphenylpropane‐1,2,3‐trione (Diphenyl Triketone)

AU - Schultz, György

AU - Hargittai, I.

AU - Doerner, Thomas

AU - Gleiter, Rolf

PY - 1991

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N2 - The molecular structure of 1,3‐diphenylpropane‐1,2,3‐trione (diphenyl triketone) has been determined by gas‐phase electron diffraction at 130°C nozzle temperature. It has been found that the phenyl rings are nearly coplanar with the adjacent carbonyl groups, and the two Cph–C(O)–C(O)–C(O) dihedral angles are ‐ 129.5 ± 0.8 and ‐ 107.1 ± 0.8° (0° corresponds to the syn form). Bond distances (rg, Å) and bond angles (deg) with estimated total errors are CH 1.105 ± 0.006, O  C 1.213 ± 0.003, < Cph–Cph> 1.404± 0.003, Cph–C(O) 1.478 ± 0.005, C(O)–C(O) 1.558 ± 0.004, Cph–C(O)–C(O) 120.0 ± 0.3, CphC(O)O 120.8 ± 0.4, C(O)–C(O)–C(O) 117.3 ± 0.4, Cph–Cph(CO)–Cph 119.8 ± 0.6. Although there is a general agreement between the gas‐phase and crystal molecular structures there are some notable differences. One of the benzene rings is slightly turned about the Cph–C(O) axis in the opposite direction in the gas molecule as compared to the crystal. This causes a marked shortening of the O… H intramolecular contact (to 2.18 Á) between the central oxygen and an ortho‐hydrogen.

AB - The molecular structure of 1,3‐diphenylpropane‐1,2,3‐trione (diphenyl triketone) has been determined by gas‐phase electron diffraction at 130°C nozzle temperature. It has been found that the phenyl rings are nearly coplanar with the adjacent carbonyl groups, and the two Cph–C(O)–C(O)–C(O) dihedral angles are ‐ 129.5 ± 0.8 and ‐ 107.1 ± 0.8° (0° corresponds to the syn form). Bond distances (rg, Å) and bond angles (deg) with estimated total errors are CH 1.105 ± 0.006, O  C 1.213 ± 0.003, < Cph–Cph> 1.404± 0.003, Cph–C(O) 1.478 ± 0.005, C(O)–C(O) 1.558 ± 0.004, Cph–C(O)–C(O) 120.0 ± 0.3, CphC(O)O 120.8 ± 0.4, C(O)–C(O)–C(O) 117.3 ± 0.4, Cph–Cph(CO)–Cph 119.8 ± 0.6. Although there is a general agreement between the gas‐phase and crystal molecular structures there are some notable differences. One of the benzene rings is slightly turned about the Cph–C(O) axis in the opposite direction in the gas molecule as compared to the crystal. This causes a marked shortening of the O… H intramolecular contact (to 2.18 Á) between the central oxygen and an ortho‐hydrogen.

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KW - Electron diffraction

KW - Gas‐crystal structure comparison

KW - Propane‐1,2,3‐trione, 1,3‐diphenyl‐

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