Electronic and molecular structures of room-temperature stable triplet carbene as studied by ESR and x-ray crystal analysis of the diazo precursor

Takeji Takui, Katsuhiko Furukawa, Koichi Itoh, Ikuko Miyahara, Ken Hirotsu, Tetsuya Watanabe, Katsuyuki Hirai, Hideo Tomioka

Research output: Contribution to journalConference article

3 Citations (Scopus)

Abstract

We report the first room-temperature stable triplet π-aryl based carbene, 2,2′,4,4′,6,6′,-hexabromodiphenylmethylene 2 in both crystals and fluid solutions. This paper describes ESR detection of 2 in the crystal of the diazo precursor 1 and the molecular and crystal structure of the precursor obtained by X-ray diffraction at room temperature. The crystal is monoclinic with cell dimensions, a = 9.993angstrom, b = 13.261angstrom, c = 12.743angstrom, θ = 91.88°, Z = 4, and the space group P21/n. The two phenyl rings of 2,4,6-bromo-substitution make bent perpendicular conformation with 139 degree of the bond angle at the diazo methane. Non-bonded contacts shorter than the van der Waals radii were found between the nitrogen and bromine atoms of the nearest neighboring molecules.

Original languageEnglish
Pages (from-to)247-252
Number of pages6
JournalMolecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals
Volume278-279
Issue numberpt 3-4
Publication statusPublished - Jan 1 1996
Externally publishedYes
EventProceedings of the 1995 12th International Conference on the Chemistry of the Organic Solid State. Part 1 & 2 (of 4) - Okudogo, Jpn
Duration: Jul 9 1995Jul 14 1995

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carbenes
Molecular structure
Electronic structure
Paramagnetic resonance
molecular structure
electronic structure
X rays
Crystals
room temperature
Diazomethane
crystals
Bromine
x rays
bromine
nitrogen atoms
Temperature
Conformations
Methane
Substitution reactions
Nitrogen

All Science Journal Classification (ASJC) codes

  • Condensed Matter Physics

Cite this

Electronic and molecular structures of room-temperature stable triplet carbene as studied by ESR and x-ray crystal analysis of the diazo precursor. / Takui, Takeji; Furukawa, Katsuhiko; Itoh, Koichi; Miyahara, Ikuko; Hirotsu, Ken; Watanabe, Tetsuya; Hirai, Katsuyuki; Tomioka, Hideo.

In: Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, Vol. 278-279, No. pt 3-4, 01.01.1996, p. 247-252.

Research output: Contribution to journalConference article

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AU - Takui, Takeji

AU - Furukawa, Katsuhiko

AU - Itoh, Koichi

AU - Miyahara, Ikuko

AU - Hirotsu, Ken

AU - Watanabe, Tetsuya

AU - Hirai, Katsuyuki

AU - Tomioka, Hideo

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N2 - We report the first room-temperature stable triplet π-aryl based carbene, 2,2′,4,4′,6,6′,-hexabromodiphenylmethylene 2 in both crystals and fluid solutions. This paper describes ESR detection of 2 in the crystal of the diazo precursor 1 and the molecular and crystal structure of the precursor obtained by X-ray diffraction at room temperature. The crystal is monoclinic with cell dimensions, a = 9.993angstrom, b = 13.261angstrom, c = 12.743angstrom, θ = 91.88°, Z = 4, and the space group P21/n. The two phenyl rings of 2,4,6-bromo-substitution make bent perpendicular conformation with 139 degree of the bond angle at the diazo methane. Non-bonded contacts shorter than the van der Waals radii were found between the nitrogen and bromine atoms of the nearest neighboring molecules.

AB - We report the first room-temperature stable triplet π-aryl based carbene, 2,2′,4,4′,6,6′,-hexabromodiphenylmethylene 2 in both crystals and fluid solutions. This paper describes ESR detection of 2 in the crystal of the diazo precursor 1 and the molecular and crystal structure of the precursor obtained by X-ray diffraction at room temperature. The crystal is monoclinic with cell dimensions, a = 9.993angstrom, b = 13.261angstrom, c = 12.743angstrom, θ = 91.88°, Z = 4, and the space group P21/n. The two phenyl rings of 2,4,6-bromo-substitution make bent perpendicular conformation with 139 degree of the bond angle at the diazo methane. Non-bonded contacts shorter than the van der Waals radii were found between the nitrogen and bromine atoms of the nearest neighboring molecules.

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