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. Author manuscript; available in PMC: 2022 Oct 15.
Published in final edited form as: ACS Chem Biol. 2021 Oct 6;16(10):1884–1893. doi: 10.1021/acschembio.1c00413

Figure 5. The CH3 bond of β-galactose is polarized by overlap with the antiperiplanar CO4 hydroxyl group.

Figure 5.

3D natural bond orbital (NBO) diagrams are depicted in panels A and B. A. Overlap between C–H3 bonding orbital and C–O4 antibonding orbital of β-D-galactose. B. Non-overlap between the C–H2 bonding orbital and C–O3 antibonding orbital of β-D-galactose. Notably, these orbitals are antiperiplanar in A and gauche in B.95 C. Resonance structures depicting polarization of the relevant C-H bonds rendering some protons with more electropositive (blue) depending on hydroxyl group stereochemistry.