アノマー効果再訪 CH/n (CH/O, CH/X) 水素結合による解釈

1. アノマー効果再訪 CH/ n (CH/O, CH/X) 水素結合による解釈 高橋 修，山崎勝義（広大） 河野雄次，上田一義（横国大） 末澤裕子（文科省），西尾元宏（ CHPI 研）

2. Anomeric effect of glucosides

3. Anomeric effect of six-member heterocyclic compounds X, Y = O, S; Z = O, halogens, etc.

4. Generalized anomeric effect

8. Difference in the Gibbs energy between ax and eq conformers G eq – G ax (  G eq-ax ) of 2-substituted oxanes 1 and 1,3-dioxanes 2

9. Bond lengths d O -C 2 and d C 2 - Z in 1

10. Bond lengths d O-C 2 and d C 2 -O and  d ax-eq in 2-methoxy oxane, glucose and glycosides

11. Non-bond distances between axial hydrogens H 4ax and H 6ax vs. Z, calculated for 2-substituted oxanes

12. Conformation of simple aliphatic molecules (5-member CH/O hydrogen bond)

13. NBO charges of the axial and equatorial conformers of in 2-methoxy oxane

14. Differences in the NBO charges between the axial and equatorial conformers of the relevant atoms in 2-substituted oxanes

15. Calculated 13 C NMR chemical shifts and the difference between the axial and equatorial conformers for C 4 and C 6 in 2-substituted oxanes (  -effect )

16. CH/O 水素結合による解釈 Eliel, J. Org. Chem . 1968 , 33 , 3754

17.  -Anomers of glycosides Lichtenthaler, Liebig Ann. Chem. 1990 , 1001

18.  -Anomers of glycosides Horton, J. Org. Chem . 1965 , 30 , 3387