3-Sphere Tetrahedral Angles and Phase Angle of the Pseudorotation P[deg] of C<sub>1</sub>-CH<sub>3</sub>-α-D Ribitol Iminocyclitol

Petru Filip; Carmen Irena Mitan; Emerich Bartha

doi:doi:10.11648/j.sjc.20241203.12

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

Petru Filip

, Carmen Irena Mitan^*

, Emerich Bartha

Published in Science Journal of Chemistry (Volume 12, Issue 3)

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

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Abstract

3-Sphere dihedral angles θ_HnHn+1[deg] calculated from NMR data, from vicinal coupling constant ³J_HnHn+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 ³J_HnHn+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 φ_Cn[deg] in close relationship with dihedral angles θ_HnHn+1[deg] are calculated only from vicinal coupling constant ³J_HnHn+1[Hz] in attempt to corelate the change in conformation with tetrahedral values φ_Cn[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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APA Style

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
AU  - Emerich Bartha
Y1  - 2024/06/19
PY  - 2024
N1  - https://doi.org/10.11648/j.sjc.20241203.12
DO  - 10.11648/j.sjc.20241203.12
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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Author Information

Petru Filip

Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

Contact Email

http://orcid.org/0000-0003-2076-7244
Carmen Irena Mitan

Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

Contact Email

http://orcid.org/0000-0002-4790-3122
Emerich Bartha

Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania

Contact Email

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APA Style

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

Copy | Download

@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}
}

Copy | Download

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
AU  - Emerich Bartha
Y1  - 2024/06/19
PY  - 2024
N1  - https://doi.org/10.11648/j.sjc.20241203.12
DO  - 10.11648/j.sjc.20241203.12
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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