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3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C1-CH3-α-D Ribitol Iminocyclitol

Received: 13 May 2024     Accepted: 30 May 2024     Published: 19 June 2024
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Abstract

3-Sphere dihedral angles θHnHn+1[deg] calculated from NMR data, from vicinal coupling constant 3JHnHn+1[Hz] with right sign and stereochemistry, are used for simulation of the conformation of the five membered ring with VISION molecular models and Gausian09W. For a vicinal angle ϕ[deg], angle result from vicinal coupling constant 3JHnHn+1[Hz], result three possible dihedral angles with negative and positive sign. Different phase angles of the pseudorotation results from combination of dihedral angles (exocyclic angles) with positive and negative sign in case of cis stereochemistry, and only negative sign for trans stereochemistry, in accord with D-ribitol stereochemistry. The sign of the endocyclic trans-ee torsional angle is positive, relative to trans-aa and cis stereochemistry with same sign as exocyclic angle, as visualized on VISION molecular models. Tetrahedral angles φCn[deg] in close relationship with dihedral angles θHnHn+1[deg] are calculated only from vicinal coupling constant 3JHnHn+1[Hz] in attempt to corelate the change in conformation with tetrahedral values φCn[deg] and bond lengths l[A0], once the iminocyclitol push out from planarity one or two atoms of carbon, and once again to confirm the method for calculation of tetrahedral angles of five membered ring, sin/tan versus sin/cos units.

Published in Science Journal of Chemistry (Volume 12, Issue 3)
DOI 10.11648/j.sjc.20241203.12
Page(s) 54-62
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

3-Sphere, Dihedral Angle, Tetrahedral Angle, Vicinal Angle, Vicinal Coupling Constant, C1-CH3-α-D-Ribitol, Conformational Analysis

References
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Cite This Article
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    Filip, P., Mitan, C. I., Bartha, E. (2024). 3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C1-CH3-α-D Ribitol Iminocyclitol. Science Journal of Chemistry, 12(3), 54-62. https://doi.org/10.11648/j.sjc.20241203.12

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    ACS Style

    Filip, P.; Mitan, C. I.; Bartha, E. 3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C1-CH3-α-D Ribitol Iminocyclitol. Sci. J. Chem. 2024, 12(3), 54-62. doi: 10.11648/j.sjc.20241203.12

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    AMA Style

    Filip P, Mitan CI, Bartha E. 3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C1-CH3-α-D Ribitol Iminocyclitol. Sci J Chem. 2024;12(3):54-62. doi: 10.11648/j.sjc.20241203.12

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  • @article{10.11648/j.sjc.20241203.12,
      author = {Petru Filip and Carmen Irena Mitan and Emerich Bartha},
      title = {3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C1-CH3-α-D Ribitol Iminocyclitol
    },
      journal = {Science Journal of Chemistry},
      volume = {12},
      number = {3},
      pages = {54-62},
      doi = {10.11648/j.sjc.20241203.12},
      url = {https://doi.org/10.11648/j.sjc.20241203.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20241203.12},
      abstract = {3-Sphere dihedral angles θHnHn+1[deg] calculated from NMR data, from vicinal coupling constant 3JHnHn+1[Hz] with right sign and stereochemistry, are used for simulation of the conformation of the five membered ring with VISION molecular models and Gausian09W. For a vicinal angle ϕ[deg], angle result from vicinal coupling constant 3JHnHn+1[Hz], result three possible dihedral angles with negative and positive sign. Different phase angles of the pseudorotation results from combination of dihedral angles (exocyclic angles) with positive and negative sign in case of cis stereochemistry, and only negative sign for trans stereochemistry, in accord with D-ribitol stereochemistry. The sign of the endocyclic trans-ee torsional angle is positive, relative to trans-aa and cis stereochemistry with same sign as exocyclic angle, as visualized on VISION molecular models. Tetrahedral angles φCn[deg] in close relationship with dihedral angles θHnHn+1[deg] are calculated only from vicinal coupling constant 3JHnHn+1[Hz] in attempt to corelate the change in conformation with tetrahedral values φCn[deg] and bond lengths l[A0], once the iminocyclitol push out from planarity one or two atoms of carbon, and once again to confirm the method for calculation of tetrahedral angles of five membered ring, sin/tan versus sin/cos units.
    },
     year = {2024}
    }
    

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  • TY  - JOUR
    T1  - 3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C1-CH3-α-D Ribitol Iminocyclitol
    
    AU  - Petru Filip
    AU  - Carmen Irena Mitan
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    T2  - Science Journal of Chemistry
    JF  - Science Journal of Chemistry
    JO  - Science Journal of Chemistry
    SP  - 54
    EP  - 62
    PB  - Science Publishing Group
    SN  - 2330-099X
    UR  - https://doi.org/10.11648/j.sjc.20241203.12
    AB  - 3-Sphere dihedral angles θHnHn+1[deg] calculated from NMR data, from vicinal coupling constant 3JHnHn+1[Hz] with right sign and stereochemistry, are used for simulation of the conformation of the five membered ring with VISION molecular models and Gausian09W. For a vicinal angle ϕ[deg], angle result from vicinal coupling constant 3JHnHn+1[Hz], result three possible dihedral angles with negative and positive sign. Different phase angles of the pseudorotation results from combination of dihedral angles (exocyclic angles) with positive and negative sign in case of cis stereochemistry, and only negative sign for trans stereochemistry, in accord with D-ribitol stereochemistry. The sign of the endocyclic trans-ee torsional angle is positive, relative to trans-aa and cis stereochemistry with same sign as exocyclic angle, as visualized on VISION molecular models. Tetrahedral angles φCn[deg] in close relationship with dihedral angles θHnHn+1[deg] are calculated only from vicinal coupling constant 3JHnHn+1[Hz] in attempt to corelate the change in conformation with tetrahedral values φCn[deg] and bond lengths l[A0], once the iminocyclitol push out from planarity one or two atoms of carbon, and once again to confirm the method for calculation of tetrahedral angles of five membered ring, sin/tan versus sin/cos units.
    
    VL  - 12
    IS  - 3
    ER  - 

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