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. Author manuscript; available in PMC: 2008 Sep 2.
Published in final edited form as: J Am Chem Soc. 2006 Apr 19;128(15):5049–5058. doi: 10.1021/ja0573054

Figure 12.

Figure 12

The antibonding orbital σ* orbital of CH1 accepts electron density from lone pair orbitals of O1 and O5. Deprotonation of OH1 increases this hyperconjugation, leading to vibrational loosening of CH1 and to a [1-d]glucose KIE between 1.0 and 1.036.