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. Author manuscript; available in PMC: 2009 Aug 3.
Published in final edited form as: Bioorg Med Chem. 2007 Nov 26;16(4):2114–2130. doi: 10.1016/j.bmc.2007.10.081

Table 6.

Energy to form intramolecular hydrogen bond (kcal/mole)a

Rb Sulfur oxidation state
Thioether Sulfoxide Sulfone
3 7.18 13.59 10.39
4 7.25 13.62 10.45
6 7.22 13.64 10.42
8 7.25 13.75 10.45
10 7.28 13.74 10.47
a

Values were calculated as the amount of energy required to break the intramolecular bond in the 5-membered ring for thioether-containing compounds or the 6-membered ring for sulfoxide- and sulfone-containing compounds as shown in Figure 1.

b

R refers to the length of the alkyl chain as shown in Figure 1.