Coupled Cluster and Density Functional Theory Studies of the Vibrational Contribution to the Optical Rotation of (S)-Propylene Oxide.

In a previous study (Chemical Physics Letters2005, 401 ,385) we computed the optical rotatory dispersion of (S)-propylene oxide in gas phase and solution using the hierarchy of coupled cluster models CCS, CC2, CCSD, and CC3. Even for the highly correlated CC3 model combined with a flexible basis set...

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Publicado en:Journal of the American Chemical Society Vol. 128; no. 3; pp. 976 - 983
Autores principales: Jacob Kongsted, Thomas Bondo Pedersen, Lasse Jensen, Aage E. Hansen, Kurt V. Mikkeisen
Formato: Artículo
Publicado: American Chemical Society 1/25/2006
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Acceso en línea:Ver este registro en EBSCOhost
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        10.1021/ja056611e
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        atl: Coupled Cluster and Density Functional Theory Studies of the Vibrational Contribution to the Optical Rotation of (S)-Propylene Oxide.
      aug:
        au:
          Jacob Kongsted
          Thomas Bondo Pedersen
          Lasse Jensen
          Aage E. Hansen
          Kurt V. Mikkeisen
        affil:
          Contribution from the Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Aarhus C, Denmark
          Department of Theoretical Chemistry, Chemical Center, University of Lund, P.O. Box 124, S-22 1 00 Lund, Sweden
          Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113
          Department of Chemistry, H. C. ∅rsted Institute, University of Copenhagen, DK-2 100 Copenhagen Ø, Denmark
      su:
        Propylene oxide
        Density functionals
        Optical polarization
        Dispersion (Chemistry)
        Molecular rotation
        Biochemistry
      sug:
        subj:
          Propylene oxide
          Density functionals
          Optical polarization
          Dispersion (Chemistry)
          Molecular rotation
          Biochemistry
      ab: In a previous study (Chemical Physics Letters2005, 401 ,385) we computed the optical rotatory dispersion of (S)-propylene oxide in gas phase and solution using the hierarchy of coupled cluster models CCS, CC2, CCSD, and CC3. Even for the highly correlated CC3 model combined with a flexible basis set, the theoretical gas-phase specific rotation at 355 nm was found to be negative in contrast to the experimental result. We argued that vibrational contributions could be crucial for obtaining a complete understanding of the experimental result. Here, we show that this indeed is the case by using coupled cluster models and density functional theory methods to calculate the vibrational contributions to the gas-phase specific rotation at 355, 589.3, and 633 nm. While density functional theory (B3LYP and SAOP functionals) overestimates the specific rotation at 355 nm by approximately 1 order of magnitude and yields an incorrect sign at 589.3 and 633 nm, the coupled cluster results are in excellent agreement with the experimentally measured optical rotations. We find that all vibrational modes contribute significantly to the optical rotation and that temperature effects must be taken into account.
      pubtype: Academic Journal
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    language: English
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