Research Article
3-Spherical Conformational Insights into Iminocyclitols with 1-α-D-Ribose and 1-β-L-Ribose Stereochemistry Under Homotopic Behaviour of Nuclear Magnetic Resonance Data
Issue:
Volume 14, Issue 1, February 2026
Pages:
1-11
Received:
22 December 2025
Accepted:
6 January 2026
Published:
2 February 2026
DOI:
10.11648/j.sjc.20261401.11
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Abstract: 3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θHnHn+1 [deg] – tetrahedral φCn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling constant 3JHH [Hz] and carbon chemical shift δC [ppm]. This approach gave for 1-α-methyl-1,4-imino-1,4-dideoxy-D-ribitol 2 two conformers E3 and 3T2 having different dihedral θHnHn+1 [deg] and tetrahedral φCn [deg] angles with same vicinal angles ϕ [deg]. Notably, phase angle of pseudorotation P [deg] placed the conformations on the south side for D-ribitols 1 - 3 and on the north side for L-ribitol 4, excepting trifluoroacetate salt of L-ribitol 5. The wave character of NMR data introduced few homotopic switches, the transformation from torus to inverse of torus, the relationship between angles of set A and set B, the transformation from Planck constants h to h-bar, along with the transformation from Joule to Calorie (J 4.1868 ⇆ J-1 0.238). Two methods for calculation of tetrahedral angles φCn [deg], energy-graph and Euler conic with two ways for representing the angles, polyhedron and unit models are analyzed. The conformational parameters, phase angle of the pseudorotation P [deg] established with VISION molecular model and exocyclic 3-Sphere dihedral angles θHnHn+1 [deg] relative to endocyclic torsional angles θn,n+1 [deg] from Altona-Sundaralingan model have been evaluated. In addition, the corresponding angle of deviation from planarity θm [deg] has been determined.
Abstract: 3-Sphere, a hypersphere in 4 dimensions approach, applied for calculating stereochemical parameters of iminocyclitol 1 – 5 with Hopf fibration and Lie algebra is described. Three angles have been considered, i.e. dihedral θHnHn+1 [deg] – tetrahedral φCn [deg] – phase angle of the pseudorotation P [deg] calculated from NMR data, vicinal coupling con...
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,
Emerich Bartha,
Petru Filip
