Hydrated sugars in the gas phase: Spectroscopy and conformation of singly hydrated phenyl β-D-glucopyranoside

Journal of Physical Chemistry A

Volumn 107, Issue 49, 2003, Pages 10725-10732

  Jockusch, Rebecca A ^a   Kroemer, Romano T ^a,b   Talbot, Francis O ^a   Simons, John P ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b Department of Chemistry Pharmacia ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPUTER SIMULATION; CONFORMATIONS; HYDRATION; IONIZATION; MOLECULAR VIBRATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE (COMPOSITION);

HYDRATED SUGARS; INFRARED ION DIP SPECTRA; PHENYL GLUPYRANOSIDE; PHOTON IONIZATION;

SUGARS;

EID: 0346885732     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0351730     Document Type: Article

References (33)

1. Talbot, F. O.; Simons, J. P. Phys. Chem. Chem. Phys. 2002, 4, 3562.
2. Philips, L. A.; Levy, D. H. J. Phys. Chem. 1986, 90, 4921.
3. Cable, J. R.; Tubergen, M. J.; Levy, D. H. J. Am. Chem. Soc. 1987, 109, 6198.
4. Cable, J. R.; Tubergen, M. J.; Levy, D. H. Faraday Discuss. 1988, 143.
5. Dian, B. C.; Longarte, A.; Zwier, T. S. Science 2002, 296, 2369.
6. Dian, B. C.; Longarte, A.; Mercier, S.; Evans, D. A.; Wales, D. J.; Zwier, T. S. J. Chem. Phys. 2002, 117, 10688.
7. Robertson, E. G.; Simons, J. P. Phys. Chem. Chem. Phys. 2001, 3, 1.
8. Zwier, T. S. J. Phys. Chem. A 2001, 105, 8827.
9. Simons, J. P. Compt. Rend. Chim. 2003, 6, 17.
10. Dong, F.; Miller, R. E. Science 2002, 298, 1227.
11. Barrows, S. E.; Dulles, F. J.; Cramer, C. J.; French, A. D.; Truhlar, D. G. Carbohydr. Res. 1995, 276, 219.
12. Barrows, S. E.; Storer, J. W.; Cramer, C. J.; French, A. D.; Truhlar, D. G. J. Comput. Chem. 1998, 19, 1111.
13. Csonka, G. I.; Elias, K.; Csizmadia, I. G. Chem. Phys. Lett. 1996, 257, 49.
14. Molteni, C.; Parrinello, M. J. Am. Chem. Soc. 1998, 120, 2168.
15. Jockusch, R. A.; Talbot, F. O.; Simons, J. P. Phys. Chem. Chem. Phys. 2003, 5, 1502.
16. Nishida, Y.; Hori, H.; Ohrui, H.; Meguro, H. J. Carbohydr. Chem. 1988, 7, 239.
17. Tvaroška, I.; Taravel, F. R.; Utille, J. P.; Carver, J. P. Carbohydr. Res. 2002, 337, 353.
18. Bock, K.; Duus, J. Ø. J. Carbohydr. Chem. 1994, 13, 513.
19. Snoek, L. C.; Robertson, E. G.; Kroemer, R. T.; Simons, J. P. Chem. Phys. Lett. 2000, 321, 49.
20. Snoek, L. C.; Kroemer, R. T.; Hockridge, M. R.; Simons, J. P. Phys. Chem. Chem. Phys. 2001, 3, 1819.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 1998.
23. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
24. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
25. Hariharan, P. C.; Pople, R. A. Theor. Chim. Acta 1973, 28, 213.
26. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. V. J. Comput. Chem. 1983, 4, 294.
27. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
28. Macleod, N. A.; Simons, J. P. Chem. Phys. 2002, 283, 221.
29. Butz, P.; Kroemer, R. T.; Macleod, N. A.; Simons, J. P. Phys. Chem. Chem. Phys. 2002, 4, 3566.
30. Graham, R. J.; Kroemer, R. T.; Mons, M.; Robertson, E. G.; Snoek, L. C.; Simons J. P. J. Phys. Chem. A 1999, 103, 9706.
31. Gerhards, M.; Unterberg, C.; Kleinermanns, K. Phys. Chem. Chem. Phys. 2000, 2, 5538.
32. -1 above the global minimum. Similarly, if the water were to act only as a proton acceptor, then it would undoubtedly act also as a proton donor to the nearby oxygen atom (to create an insertion structure) because every hydroxyl group on the sugar ring is close to another oxygen atom, with which it interacts weakly.
33. When contacted regarding these difficulties, Gaussian technical support confirmed that older versions of Gaussian suffered from an algorithmic error in how coordinates were chosen for some complexes, which could result in false minima. Here, we highlight the dangers of over-reliance on default optimization procedures because we believe this may be relevant to the increasing number of researchers studying noncovalent complexes.