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 |
3-Sphere, Dihedral Angle, Tetrahedral Angle, Vicinal Angle, Vicinal Coupling Constant, C1-CH3-α-D-Ribitol, Conformational Analysis
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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
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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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}
}
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 -
Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania
Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania
Department of Chemistry, “C. D. Nenitescu” Institute of Organic and Supramolecular Chemistry, Bucharest, Romania
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