Structural Expression of Exo-Anomeric Effect

Transcript

1 Supporting Information for Structural Expression of Exo-Anomeric Effect Elena R. Alonso, Isabel Peña, Carlos Cabezas, and José L. Alonso* Contents Table S1: Transition frequencies of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside. Table S2-S4: Cartesian coordinates for the three lower-energy conformers of methyl β- D-xyloside. Table S5-S15: Transition frequencies of 13 C and 18 O monosubstituted isotopologues of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside. Table S16: Substitution coordinates for conformer cc-β- 4 C 1 g- of methyl β-dxylopyranoside. Table S17: Experimental results of methyl β-d-xyloside and comparison with theoretical predictions. Complete reference 30 S1

2 Table S1. Observed frequencies and residuals (in MHz) for the rotational transitions of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside. obs ν obs - ν cal S2

3 Table S2. Cartesian coordinates for the c-β- 4 C 1 g- conformer. The geometries have been optimized ab initio at the MP2/ G(d,p) level of theory. Center Atomic Coordinates (Angstroms) Number Number X Y Z Rotational constants (MHZ): S3

4 Table S3. Cartesian coordinates for the cc-β- 4 C 1 g+ conformer. The geometries have been optimized ab initio at the MP2/ G(d,p) level of theory. Center Atomic Coordinates (Angstroms) Number Number X Y Z Rotational constants (MHZ): Table S4. Cartesian coordinates for the cc-β- 4 C 1 g- conformer. The geometries have been optimized ab initio at the MP2/ G(d,p) level of theory. Center Atomic Coordinates (Angstroms) Number Number X Y Z Rotational constants (MHZ): S4

5 Table S5. Observed frequencies and residuals (in MHz) for the rotational transitions of 13 C 1 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside Table S6. Observed frequencies and residuals (in MHz) for the rotational transitions of 13 C 2 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside S5

6 Table S7. Observed frequencies and residuals (in MHz) for the rotational transitions of 13 C 3 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside Table S8. Observed frequencies and residuals (in MHz) for the rotational transitions of 13 C 4 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside S6

7 Table S9. Observed frequencies and residuals (in MHz) for the rotational transitions of 13 C 5 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside Table S10. Observed frequencies and residuals (in MHz) for the rotational transitions of 13 C 6 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside S7

8 Table S11. Observed frequencies and residuals (in MHz) for the rotational transitions of 18 O 1 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside Table S12. Observed frequencies and residuals (in MHz) for the rotational transitions of 18 O 2 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside Table S13. Observed frequencies and residuals (in MHz) for the rotational transitions of 18 O 3 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside S8

9 Table S14. Observed frequencies and residuals (in MHz) for the rotational transitions of 18 O 4 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside Table S15. Observed frequencies and residuals (in MHz) for the rotational transitions of 18 O 5 monosubstituted isotopologue of conformer cc-β- 4 C 1 g- of methyl β-d-xyloside S9

10 Table S16. Substitution coordinates for conformer cc-β- 4 C 1 g- of methyl β-dxylopyranoside. atom a b c C (14) (34) (76) C (18) (16) (64) C (13) (27) (72) C (10) (20) (57) C (32) (90) (98) C (45) (26) (80) O (64) (70) (52) O (34) (75) (54) O (73) (11) (58) O (57) (13) (59) O (20) (11) (45) a Principal inertial axis coordinates in Å; derived errors in parentheses in units of the last digit; These were calculated according to Constains formula: σ(x) = K/ x ; σ(x) is the error in the x coordinate and K = Å 2. S10

11 Table S17. Experimental results of methyl β-d-xyloside and comparison with theoretical predictions. Experimental MP2/B3LYP/M06HF/M05-2X /M06-2X G(d,p) MP2/B3LYP/M06HF/M05-2X /M06-2X cc-pvtz MP2/B3LYP/M06HF/M05-2X /M06-2X Aug-cc-pVTZ A a / MHz (72) c /1756.3/1779.0/1783.3/ /1765.4/1782.9/1790.2/ /1762.0/1781.9/1788.1/ B/ MHz (24) 833.0/ 820.0/834.9/835.6/ /822.7/836.1/837.8/ /821.2/835.2/836.7/836.2 C/ MHz (17) 595.4/586.9/595.8/597.1/ /589.2/597.0/598.9/ /588.1/596.4/598.1/597.0 r (C 1 -O 1 ) b /Å (77) 1.387/1.389/1.382/1.384/ /1.388/1.382/1.384/ /1.388/1.381/1.383/1.381 a A, B and C are the rotational constants. b C 1 -O 1 bond distance. c Standard error in parentheses in units of the last digit. S11

12 Complete Reference 30: Gaussian 09 (Revision B.01), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford CT, S12