The anomeric effect revisited. A possible role of the CH/n hydrogen bond

Carbohydrate Research

Volumn 342, Issue 9, 2007, Pages 1202-1209

  Takahashi, Osamu ^a   Yamasaki, Katsuyoshi ^a   Kohno, Yuji ^b   Ohtaki, Ryuta ^b   Ueda, Kazuyoshi ^b   Suezawa, Hiroko ^c   Umezawa, Yoji ^d   Nishio, Motohiro ^e  

^a HIROSHIMA UNIVERSITY   (Japan)

^b YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^c Japan Ministry of Education Culture Sports Science and Technology   (Japan)

^d INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^e CHPI Institute   (Japan)

Author keywords

1,3 Dioxane; 13C effect; Ab initio calculation; Axial preference; CH halogen hydrogen bond; CH n hydrogen bond; Natural bonding orbital; Oxane; Pyranose

Indexed keywords

CONFORMATIONS; COVALENT BONDS; ELECTRONS; GIBBS FREE ENERGY; HYDROGEN BONDS; NUMERICAL ANALYSIS; STABILIZATION;

AB INITIO CALCULATIONS; AXIAL CONFORMERS; AXIAL PREFERENCE; GAMMA EFFECTS; NATURAL BONDING ORBITALS; OXANES;

CARBOHYDRATES;

1,3 DIOXANE DERIVATIVE; BROMINE; CARBOHYDRATE; CARBON; CHLORINE; FLUORINE; HALOGEN; HYDROGEN; OXYGEN;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CONFORMATION; CRYSTALLOGRAPHY; DATA BASE; ELECTRON; ENERGY TRANSFER; HYDROGEN BOND; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

DIOXANES; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; STEREOISOMERISM; THERMODYNAMICS;

EID: 34247593892     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2007.02.032     Document Type: Article

References (52)

1. Edward J.T. Chem. Ind. (London) (1955) 1102-1104
2. Lemieux R.U. Pure Appl. Chem. 25 (1971) 527-548
3. Juaristi E., and Cuevas G. Tetrahedron 48 (1992) 5019-5087
4. Romers C., Altona C., Buys H.R., and Havinga E. Top. Stereochem. 4 (1969) 39-97
5. Wolfe S., Rauk A., Tel L.M., and Csizmadia I.G. J. Chem. Soc. B (1971) 136-145
6. Wolfe S., and Shi X. Israel J. Chem. 40 (2000) 343-355
7. Jeffrey G.A., Pople J.A., and Radom L. Carbohydr. Res. 25 (1972) 117-131
8. David S., Eisenstein O., Hehre W.J., Salem L., and Hoffmann R. J. Am. Chem. Soc. 95 (1973) 3806-3807
9. Jeffrey G.A., Pople J.A., and Radom L. Carbohydr. Res. 38 (1974) 81-95
10. Jeffrey G.A., Pople J.A., Binkley J.S., and Vishveshwara S. J. Am. Chem. Soc. 100 (1978) 373-379
11. Wolfe S., Whangbo M.-H., and Mitchell D.J. Carbohydr. Res. 69 (1979) 1-26
12. Jeffrey G.A., and Yates J.H. J. Am. Chem. Soc. 101 (1979) 820-825
13. Wiberg K.B., and Murcko M.A. J. Am. Chem. Soc. 111 (1989) 4821-4828
14. Krol M.C., Huige C.J.M., and Altona C. J. Comput. Chem. 11 (1990) 765-790
15. Smith G.D., Jaffe R.L., and Yoon D.Y. J. Phys. Chem. 98 (1994) 9072-9077
16. Kneisler J.R., and Allinger N.L. J. Comput. Chem. 17 (1996) 757-766
17. Favero L.B., Caminati W., and Verino B. Phys. Chem. Chem. Phys. 5 (2003) 4776-4779
18. Fuchs B., Schleifer L., and Tartakovsky E. New J. Chem. 8 (1984) 275-278
19. Schleifer L., Senderowitz H., Aped P., Tartakovsky E., and Fuchs B. Carbohydr. Res. 206 (1990) 21-39
20. Allen F.H. Acta Crystallogr., Sect. A 54 (1998) 758-771
21. Allen F.H. Acta Crystallogr., Sect. B 58 (2002) 380-388
22. Trapp M.L., Watts J.K., Weinberg N., and Pinto B.M. Can. J. Chem. 84 (2006) 692-701
23. Pinto B.M., Schlegel H.B., and Wolfe S. Can. J. Chem. 65 (1987) 1658-1662
24. Wolfe S., Pinto B.M., Varma V., and Leung R.Y.N. Can. J. Chem. 68 (1990) 1051-1062
25. Cramer C.J. J. Org. Chem. 57 (1992) 7034-7043
26. Salzner U., and von Raugé Schleyer P. J. Am. Chem. Soc. 115 (1993) 10231-10236
27. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. gaussian 03, Revision C.02 (2004), Gaussian, Wallingford CT
28. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO (version 3.1).
29. Booth G.E., and Ouellette R.J. J. Org. Chem. 31 (1966) 544-546
30. Eliel E.L., and Giza C.A. J. Org. Chem. 33 (1968) 3754-3758
31. Bailey W.M., and Eliel E.L. J. Am. Chem. Soc. 96 (1974) 1798-1806
32. Eliel E.L., and Knoeber M.C. J. Am. Chem. Soc. 90 (1968) 3444-3458
33. Momany F.A., Appel M., Willett J.L., and Bosma W.B. Carbohydr. Res. 340 (2005) 1638-1655
34. Praly J.-P., and Lemieux R.U. Can. J. Chem. 65 (1987) 213-223
35. Bondi A. J. Phys. Chem. 68 (1964) 441-451
36. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford Univ. Press, Oxford
37. Nishio M. Weak Hydrogen Bonds. In: Atwood J.L., and Steed J.W. (Eds). Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, New York 1576-1585
38. Zushi S., Kodama Y., Nishihata K., Umemura K., Nishio M., Uzawa J., and Hirota M. Bull. Chem. Soc. Jpn. 53 (1980) 3631-3640
39. Takahashi O., Yasunaga K., Gondoh Y., Kohno Y., Saito K., and Nishio M. Bull. Chem. Soc. Jpn. 75 (2002) 1777-1783
40. Takahashi O., Saito K., Kohno Y., Suezawa H., Ishihara S., and Nishio M. New J. Chem. 28 (2004) 355-360
41. Yoshida H., Kaneko I., Matsuura H., Ogawa Y., and Tasumi M. Chem. Phys. Lett. 196 (1992) 601-606
42. Yoshida H., Tanaka T., and Matsuura H. Chem. Lett. (1996) 637-638
43. Penner G.H., Schaeffer T., Sebastian R., and Wolfe S. Can. J. Chem. 65 (1987) 1845-1852
44. Luger P., Buschmann J., and Schmidt H.-J. Acta Crystallogr., Sect. B 38 (1982) 2732-2735
45. Kroschwitz J.I., Winokur M., Reich H.J., and Roberts J.D. J. Am. Chem. Soc. 91 (1969) 5927-5928
46. Jackman L.M., and Kelly D.P. J. Chem. Soc., B (1970) 102-110 110-113
47. Levy G.C., and Nelson G.L. J. Am. Chem. Soc. 94 (1972) 4897-4901
48. Lichtenthaler F.W., Rönninger S., and Kreis U. Liebigs Ann. Chem. (1990) 1001-1006
49. Horton D., and Turner W.M. J. Org. Chem. 30 (1965) 3387-3394
50. Durette P.L., and Horton D. Carbohydr. Res. 18 (1971) 57-80 and references cited therein
51. Hall L.D., and Manville J.F. Carbohydr. Res. 4 (1967) 512-513
52. Perrin C.L., Armstrong K.B., and Fabian M.A. J. Am. Chem. Soc. 116 (1994) 715-722