The origin of the generalized anomeric effect: possibility of CH/n and CH/π hydrogen bonds

Carbohydrate Research

Volumn 344, Issue 10, 2009, Pages 1225-1229

  Takahashi, Osamu ^a   Yamasaki, Katsuyoshi ^a   Kohno, Yuji ^b   Ueda, Kazuyoshi ^b   Suezawa, Hiroko ^c   Nishio, Motohiro ^d  

^a HIROSHIMA UNIVERSITY   (Japan)

^b YOKOHAMA NATIONAL UNIVERSITY   (Japan)

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

^d CHPI Institute   (Japan)

Author keywords

Ab initio calculation; CH hydrogen bond; CH n hydrogen bond; Gauche conformation; NBO charge; Nonbonded distance

Indexed keywords

AB INITIO CALCULATION; CH/N HYDROGEN BOND; GAUCHE CONFORMATION; NBO CHARGE; NONBONDED DISTANCE;

BINDING SITES; ETHERS; GIBBS FREE ENERGY; HYDROGEN; VAN DER WAALS FORCES;

HYDROGEN BONDS;

AB INITIO CALCULATION; ARTICLE; CONFORMATION; ENERGY; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; PRIORITY JOURNAL;

ACETALDEHYDE; CARBOHYDRATE CONFORMATION; GLYCOSIDES; HALOGENS; HYDROGEN BONDING; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 66649115410     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.04.011     Document Type: Article

References (75)

1. Lemieux R.U. Pure Appl. Chem. 25 (1971) 527-548
2. Juaristi E., and Cuevas G. Tetrahedron 48 (1992) 5019-5087
3. Edward J.T. Chem. Ind. (London) (1955) 1102-1104
4. Perrin C.L., Armstrong K.B., and Fabian M.A. J. Am. Chem. Soc. 116 (1994) 715-722
5. Lucken E.A.C. J. Chem. Soc. (1959) 2954-2960
6. Romers C., Altona C., Buys H.R., and Havinga E. Top. Stereochem. 4 (1969) 39-97
7. Ardalan Z., and Lucken E.A.C. Helv. Chim. Acta 56 (1973) 1715-1719
8. Wolfe S., Rauk A., Tel L.M., and Csizmadia I.G. J. Chem. Soc. B (1971) 136-145
9. Wolfe S., Whangbo M.-H., and Mitchell D.J. Carbohydr. Res. 69 (1979) 1-26
10. Radom L., Hehre W.J., and Pople J.A. J. Am. Chem. Soc. 93 (1971) 289-300
11. Pinto B.M., Schlegel H.B., and Wolfe S. Can. J. Chem. 65 (1987) 1658-1662
12. Wolfe S., Pinto B.M., Varma V., and Leung R.Y.N. Can. J. Chem. 68 (1990) 1051-1062
13. Wolfe S., and Shi X. Israel J. Chem. 40 (2000) 343-355
14. David S., Eisenstein O., Hehre W.J., Salem L., and Hoffmann R. J. Am. Chem. Soc. 95 (1973) 3806-3807
15. Wiberg K.B., and Murcko M.A. J. Am. Chem. Soc. 111 (1989) 4821-4828
16. Krol M.C., Huige C.J.M., and Altona C. J. Comput. Chem. 11 (1990) 765-790
17. Smith G.D., Jaffe R.L., and Yoon D.Y. J. Phys. Chem. 98 (1994) 9072-9077
18. Kneisler J.R., and Allinger N.L. J. Comput. Chem. 17 (1996) 757-766
19. Jeffrey G.A., Pople J.A., and Radom L. Carbohydr. Res. 25 (1972) 117-131
20. Jeffrey G.A., Pople J.A., and Radom L. Carbohydr. Res. 38 (1974) 81-95
21. Jeffrey G.A., Pople J.A., Binkley J.S., and Vishveshwara S. J. Am. Chem. Soc. 100 (1978) 373-379
22. Jeffrey G.A., and Yates J.H. J. Am. Chem. Soc. 101 (1979) 820-825
23. Takahashi O., Yamasaki K., Kohno Y., Ohtaki R., Ueda K., Suezawa H., Umezawa Y., and Nishio M. Carbohydr. Res. 342 (2007) 1202-1209
24. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford Univ. Press, New York
25. Nishio M. In: Atwood J.L., and Steed J.W. (Eds). Weak Hydrogen Bonds in Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, New York 1576-1585
26. Nishio M., Hirota M., and Umezawa Y. The CH/π Interaction: Evidence, Nature, and Consequences (1998), Wiley-VCH, New York
27. Nishio M., and Hirota M. Tetrahedron 45 (1989) 7201-7245
28. Nishio M., Hirota M., Umezawa Y., and Takeuchi Y. Tetrahedron 51 (1995) 8665-8711
29. Nishio M. CrystEngCommun 6 (2004) 130-156
30. Nishio M. Tetrahedron 61 (2005) 6923-6950
31. Nishio M., and Umezawa Y. Top. Stereochem. 25 (2006) 255-302
32. Nishio, M.; Umezawa, Y.; Honda, K.; Tsuboyama, S.; Suezawa, H. CrystEngCommun 2009, in press.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; Pople, J. A. gaussian 03, Revision C.02, Gaussian: Wallingford, CT, 2004.
34. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO (version 3.1).
35. nS
36. Montagnani R., and Tomasi J. Int. J. Quantum Chem. 39 (1991) 851-870
37. Vila A., and Mosquera R.A. J. Comput. Chem. 28 (2007) 1516-1530
38. Durig J.R., Liu J., Guirgis G.A., and Veken B.J. Struct. Chem. 4 (1993) 103-126
39. Durig J.R., Tang Q., and Phan H.V. J. Raman Spectrosc. 24 (1993) 851-865
40. Durig J.R., Tang Q., and Phan H.V. J. Mol. Struct. 320 (1994) 193-216
41. Shin-ya K., Takahashi O., Katsumoto Y., and Ohno K. J. Mol. Struct. 827 (2007) 155-164
42. Ducati L.C., Freitas M.P., Tormena C.F., and Rittner R. J. Mol. Struct., THEOCHEM 851 (2008) 147-157
43. Tsuzuki S., Uchimaru T., and Tanabe K. J. Mol. Struct., THEOCHEM 366 (1996) 89-96
44. Sakaki S., Kato K., Miyazaki T., Musashi Y., Ohkubo K., Ihara H., and Hirayama C. J. Chem. Soc., Faraday Trans. 89 (1993) 659-664
45. Tsuzuki S., Honda K., Uchimaru T., Mikami M., and Tanabe K. J. Phys. Chem. A 103 (1999) 8265-8271
46. Gu Y., Kar T., and Scheiner S. J. Am. Chem. Soc. 121 (1999) 9411-9422
47. Novoa J.J., and Mota F. Chem. Phys. Lett. 318 (2000) 345-354
48. Spectroscopic evidence:. Yoshida H., Kaneko I., Matsuura H., Ogawa Y., and Tasumi M. Chem. Phys. Lett. 196 (1992) 601-606
49. Yoshida H., Tanaka T., and Matsuura H. Chem. Lett. (1996) 637-638
50. Favero L.B., Caminati W., and Verino B. Phys. Chem. Chem. Phys. 5 (2003) 4776-4779
51. MO calculations:. Takahashi O., Yasunaga K., Gondoh Y., Kohno Y., Saito K., and Nishio M. Bull. Chem. Soc. Jpn. 75 (2002) 1777-1783
52. Takahashi O., Saito K., Kohno Y., Suezawa H., Ishihara S., and Nishio M. New J. Chem. 28 (2004) 355-360
53. Penner G.H., Schaeffer T., Sebastian R., and Wolfe S. Can. J. Chem. 65 (1987) 1845-1852
54. Takahashi O., Yamasaki K., Kohno Y., Ueda K., Suezawa H., and Nishio M. Chem. Phys. Lett. 440 (2007) 64-69
55. Spectroscopic evidence:. Oki M., and Iwamura H. Bull. Chem. Soc. Jpn. 32 (1959) 1135-1143
56. Takahashi O., Saito K., Kohno Y., Suezawa H., Ishihara S., and Nishio M. Eur. J. Org. Chem. (2004) 2398-2403
57. Takahashi O., Saito K., Kohno Y., Suezawa H., Ishihara S., and Nishio M. Bull. Chem. Soc. Jpn. 76 (2003) 2167-2173
58. Crystallographic evidence:. Ueji S., Nakatsu K., Yoshioka H., and Kinoshita K. Tetrahedron Lett. (1982) 1173-1176
59. Nakatsu K., Yoshioka H., Kunimoto K., Kinugasa T., and Ueji S. Acta Crystallogr., Sect. B (1978) 2357-2359
60. Oki M., and Mutai T. Tetrahedron 26 (1970) 1181-1198
61. Spectroscopic evidence:. Zushi S., Kodama Y., Nishihata K., Umemura K., Nishio M., Uzawa J., and Hirota M. Bull. Chem. Soc. Jpn. 53 (1980) 3631-3640
62. Suezawa H., Hashimoto T., Tsuchinaga K., Yoshida T., Yuzuri T., Sakakibara K., Hirota M., and Nishio M. J. Chem. Soc., Perkin Trans. 2 (2000) 1243-1249
63. CSD study:. Suezawa H., Yoshida T., Umezawa Y., Tsuboyama S., and Nishio M. Eur. J. Inorg. Chem. (2002) 3148-3155
64. Suezawa H., Ishihara S., Takahashi O., Saito K., Kohno Y., and Nishio M. New J. Chem. 27 (2003) 1609-1613
65. MO calculations:. Takahashi O., Kohno Y., Gondoh Y., Saito K., and Nishio M. Chem. Eur. J. 9 (2003) 756-762
66. Takahashi O., Yamasaki K., Kohno Y., Ueda K., Suezawa H., and Nishio M. Chem. Asian J. 1 (2006) 852-859
67. Takahashi O., Yamasaki K., Kohno Y., Kurihara Y., Ueda K., Umezawa Y., Suezawa H., and Nishio M. Tetrahedron 64 (2008) 2433-2440
68. Takahashi O., Yamasaki K., Kohno Y., Ueda K., Umezawa Y., Suezawa H., and Nishio M. Tetrahedron 64 (2008) 5773-5778
69. Takahashi O., Yamasaki K., Kohno Y., Ueda K., Umezawa Y., Suezawa H., and Nishio M. Tetrahedron 65 (2009) 3525-3528
70. Thomas T.D., Sæthre L.J., and Børve K.J. Phys. Chem. Chem. Phys. 9 (2007) 719-724
71. Holme A., Sæthre L.J., Børve K.J., and Thomas T.D. J. Mol. Struct. 920 (2009) 387-392
72. Bondi A. J. Phys. Chem. 68 (1964) 441-451
73. Rowland R.S., and Taylor R. J. Phys. Chem. 100 (1996) 7384-7391
74. Cotton F.A., Wilkinson G., and Gaus P.L. Basic Inorganic Chemistry. 2nd ed. (1987), Wiley, New York Fig. 2.15
75. Cuevas G., Martinez-Mayorga K., Fernandez-Alonzo M., Jumenez-Barvero J., Perrin C.L., Juaristi E., and Lopez-Mora N. Angew. Chem., Int. Ed. 44 (2005) 2360-2364