Optical activity of oxo amide crystals

Toru Asahi, Makoto Nakamura, Jinzo Kobayashi, Fumio Toda, Hisakazu Miyamoto

    Research output: Contribution to journalArticle

    19 Citations (Scopus)

    Abstract

    It has been known that oxo amide crystals made up of achiral molecules can be photochemically converted into optically active β-lactams by irradiation with a high pressure mercury lamp. Although the oxo amide crystal belongs to an enantiomorphic class D2, its optical activity could not be detected so far. We successfully measured the components of the gyration tensor of the oxo amide crystal by using the HAUP (high accuracy universal polarimeter) method: g11 = -3.5 x 10-4 (-79°/mm), g22 = -1.4 x 10-4 (-32°/mm), g33 = -3.0 x 10-4 (-68°/mm) at 305 K, where the optical rotatory powers are indicated in parentheses. It has been proved by direct experiments that the optical activity of the reactant and the product in this reaction system remains unchanged over the photocyclization process.

    Original languageEnglish
    Pages (from-to)3665-3669
    Number of pages5
    JournalJournal of the American Chemical Society
    Volume119
    Issue number16
    DOIs
    Publication statusPublished - 1997 Apr 23

    Fingerprint

    Optical Rotation
    Amides
    Crystals
    Mercury vapor lamps
    Lactams
    Polarimeters
    Mercury
    Tensors
    Irradiation
    Pressure
    Molecules
    Experiments

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Asahi, T., Nakamura, M., Kobayashi, J., Toda, F., & Miyamoto, H. (1997). Optical activity of oxo amide crystals. Journal of the American Chemical Society, 119(16), 3665-3669. https://doi.org/10.1021/ja9620189

    Optical activity of oxo amide crystals. / Asahi, Toru; Nakamura, Makoto; Kobayashi, Jinzo; Toda, Fumio; Miyamoto, Hisakazu.

    In: Journal of the American Chemical Society, Vol. 119, No. 16, 23.04.1997, p. 3665-3669.

    Research output: Contribution to journalArticle

    Asahi, T, Nakamura, M, Kobayashi, J, Toda, F & Miyamoto, H 1997, 'Optical activity of oxo amide crystals', Journal of the American Chemical Society, vol. 119, no. 16, pp. 3665-3669. https://doi.org/10.1021/ja9620189
    Asahi T, Nakamura M, Kobayashi J, Toda F, Miyamoto H. Optical activity of oxo amide crystals. Journal of the American Chemical Society. 1997 Apr 23;119(16):3665-3669. https://doi.org/10.1021/ja9620189
    Asahi, Toru ; Nakamura, Makoto ; Kobayashi, Jinzo ; Toda, Fumio ; Miyamoto, Hisakazu. / Optical activity of oxo amide crystals. In: Journal of the American Chemical Society. 1997 ; Vol. 119, No. 16. pp. 3665-3669.
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