Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

doi:10.1007/s40242-013-2293-6

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3): 551-555.doi: 10.1007/s40242-013-2293-6

• Articles • Previous Articles Next Articles

Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

PAN Xiao-liang¹, ZHOU Yi-xuan², LIU Wei¹, LIU Jing-yao¹, DONG Hai²

1. State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130021, P. R. China;
2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, P. R. China

Received:2012-08-06 Revised:2012-09-26 Online:2013-06-01 Published:2013-05-15
Contact: Jing-yao Liu E-mail:ljy121@jlu.edu.cn; hdong@mail.hust.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.20973077), the Program for New Century Excellent Talents in University of China(No.NCET-07-0358) and the Brain Gain Fund of Huazhong University of Science and Technology, China.

Abstract

Abstract:

A mechanism about the origin of the selectivities for the cleavage of dioxolane five-membered rings on pyranoside rings was suggested. Quantum chemical studies were performed to testify the rationality of the mechanism. It is thus suggested that the selectivities should be dependent on the differences of the free energy at the transition states when the five-membered ring cleaves. Natural bond orbital(NBO) analysis was further made to assess the influence of stereoelectronic effects on the selectivities.

Key words: Stereoelectronic effect, Carbohydrate, Antiperiplanar lone-pair hypothesis

PAN Xiao-liang, ZHOU Yi-xuan, LIU Wei, LIU Jing-yao, DONG Hai. Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates[J]. Chemical Research in Chinese Universities, 2013, 29(3): 551-555.

References

[1] Sanassy P., Evans S. D., Langmuir, 1993, 9, 1024

[2] Cayci D., Stanciu S. G., Capan I., Erdogan M., Guner B., Hristu R., Stanciu G. A., Sensor Actuat B, Chem., 2011, 158, 62

[3] Graf K., Riegler H., Colloids Surf. A, 1998, 131, 215

[4] Petty M. C., Langmuir-Blodgett Films: An Introduction, Cambridge University Press, Cambridge, 1996

[5] George L. Gaines, Insoluble Monolayers at Liquid-gas Interface, Inter- science, New York, 1966

[6] Cao Z., Chen Q., Wang C., Ren Y., Liu H., Hu Y., Colloids Surf. A, 2011, 377, 130

[7] Song E., Shi C., Anson F. C., Langmuir, 1998, 14, 4315

[8] Dunbar A. D. F., Richardson T. H., McNaughton A. J., Hutchinson J., Hunter C. A., J. Phys. Chem. B, 2006, 110, 16646

[9] Schmidtke J. P., Friend R. H., Kastler M., Mullen K., J. Chem. Phys., 2006, 124, 174704

[10] Ferreira M., Constantino C. J. L., Olivati C. A., Balogh D. T., Aroca R. F., Faria R. M., Oliveira O. N. Jr., Polymer, 2005, 46, 5140

[11] de Luca G., Pollicino G., Romeo A., Scolaro L. M., Chem. Mater., 2006, 18, 2005

[12] Rana A. F., Frank J. M., J. Chem. Phys., 1973, 59, 5529

[13] Ignes-Mullol J., Claret J., Reigada R., Sagues F., Phys. Rep., 2007, 448, 163

[14] Tanaka H., Kunai Y., Sato N., Matsuyama T., J. Colloid Interface Sci., 2011, 363, 440

[15] Su A., Tan S., Thapa P., Flanders B. N., Ford W. T., J. Phys. Chem. C, 2007, 111, 4695

[16] Ghaicha L., Chattopadhyay A. K., Tajmir-Riahi H. A., Langmuir, 1991, 7, 2007

[17] Yazdanian M., Yu H., Zografi G., Langmuir, 1990, 6, 1093

[18] Hwang M. J., Kim K., Langmuir, 1999, 15, 3563

[19] Munden J. W., Blois D. W., Swarbrick J., J. Pharm. Sci., 1969, 58, 1308

[20] Houmadi S., Ciuchi F., de Santo M. P., de Stefano L., Rea I., Giardina P., Armenante A., Lacaze E., Giocondo M., Langmuir, 2008, 24, 12953

[21] Nayak A., Suresh K. A., Kumar Pal S., Kumar S., J. Phys. Chem. B, 2007, 111, 11157

[22] Liu M. T., Pu M. F., Ma H. W., Chem. J. Chinese Universities, 2012, 33(6), 1319

[23] Moghaddam B., Ali M. H., Wilkhu J., Kirby D. J., Mohammed A. R., Zheng Q., Perrie Y., Int. J. Pharm., 2011, 417, 235

[24] Shi W. X., Guo H. X., J. Phys. Chem. B, 2010, 114, 6365

[25] Javanainen M., Monticelli L., de la Serna J. B., Vattulainen I., Langmuir, 2010, 26, 15436

[26] Henry D. J., Dewan V. I., Prime E. L., Qiao G. G., Solomon D. H., Yarovsky I., J. Phys. Chem. B, 2010, 114, 3869

[27] Giner-Casares J. J., Camacho L., Martin-Romero M. T., Lopez Cascales J. J., Langmuir, 2008, 24, 1823

[28] Knobler C. M., Advances in Chemical Physics, John Wiley & Sons, Inc., New York, 2007, 397

[29] Langmuir I., J. Am. Chem. Soc., 1917, 39,1848

[30] Griffith E. C., Adams E. M., Allen H. C., Vaida V., J. Phys. Chem. B, 2012, 116, 7849

[31] Shaitan K. V., Pustoshilov P. P., Biophysics, 1991, 44, 429

[32] Okamura E., Fukushima N., Hayashi S., Langmuir, 1999, 15, 3589

[33] Lee Y. L., Yang Y. C., Shen Y. J., J. Phys. Chem. B, 2005, 109, 4662

[34] Moller M. A., Tildesley D. J., Kim K. S., Quirke N., J. Chem. Phys., 1991, 94, 8390

[35] Berendsen H. J. C., Postma J. P. M., van Gunsteren W. F., Hermans J., Intermolecular Forces, 1981, 331

[36] Feng C., Paul E. S., J. Chem. Phys., 2007, 126, 221101

[37] Abascal J. L. F., Vega C., J. Chem. Phys., 2005, 123, 234505

[38] Jose A., Gustavo A. C., J. Chem. Phys., 2010, 132, 014701

[39] Jorgensen W. L., Maxwell D. S., Tirado Rives J., J. Am. Chem. Soc., 1996, 118, 11225

[40] Jorgensen W. L., Chandrasekhar J., Madura J. D., Impey R. W., Klein M. L., J. Chem. Phys., 1983, 79, 926

[41] Berendsen H. J. C., Vanderspoel D., Vandrunen R., Comput. Phys. Commun., 1995, 91, 43

[42] Lindahl E., Hess B., van der Spoel D., J. Mol. Model., 2001, 7, 306

[43] van der Spoel D., Lindahl E., Hess B., Groenhof G., Mark A. E., Berendsen H. J. C., J. Comput. Chem., 2005, 26, 1701

[44] Hess B., Kutzner C., van der Spoel D., Lindahl E., J. Chem. Theory Comput., 2008, 4, 435

[45] Tom D., Darrin Y., Lee P., J. Chem. Phys., 1993, 98, 10089

[46] Bussi G., Donadio D., Parrinello M., J. Chem. Phys., 2007, 126, 014101

[47] Harris J. G., J. Phys. Chem., 1992, 96, 5077

[48] Kaminski G. A., Friesner R. A., Tirado Rives J., Jorgensen W. L., J. Phys. Chem. B, 2001, 105, 6474

[49] Marcus G. M., Fluid Phase Equilib., 2006, 248, 50

[50] Humphrey W., Dalke A., Schulten K., J. Mol. Graphics Modell, 1996, 14, 33

[51] Ghosh S., Il Nuovo Cimento D, 1984, 4, 229

Stereoelectronic Control of Cleavage of Dioxolane Five-membered Ring on Carbohydrates

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 1

Recommended Articles

Metrics

Comments