Browse > Article
http://dx.doi.org/10.5012/bkcs.2005.26.8.1229

Density Functional Theory Demonstration of Anomeric Effect and Structure: Conformational and Configurational Analysis of N-2-(1,4-Dioxane)-N'-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy) Isourea  

Dabbagh, Hossein A. (Department of Chemistry, Isfahan University of Technology)
Najafi Chermahini, Ali Reza (Department of Chemistry, Isfahan University of Technology)
Modarresi-Alam, Ali Reza (Department of Chemistry, Sistan & Baluchestan University)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.8, 2005 , pp. 1229-1234 More about this Journal
Abstract
The conformational, configurtational behavior and the structure of N-2-(1,4-Dioxane)-N'-(4-methylbenzenesulfonyl)-O-(4-methylphenoxy) isourea 1 has been studied using DFT method. Calculations predict the imidoyl amino group of the dioxane ring prefers axial conformation and that the tosyl and tolyl groups about the C=N bond retain E configuration. The anomeric effect controls the population of dioxane ring conformers, and anomers. Intramolecular hydrogen bonds contribute to the stability of E isomers. The computational analysis of 1 complements the X-ray findings.
Keywords
DFT; Anomeric effect; Conformational analysis; Configurational analysis; Hydrogen bonding;
Citations & Related Records

Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 6
연도 인용수 순위
1 Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994
2 Bushweller, C. H. Stereochemistry of Cyclohexane and Substituted Cyclohexanes. Substituted A Values in Conformational Behavior of Six-Membered Ring Analysis, Dynamics and Stereoelectronic Effects; Juaristi, E., Ed.; VHC/Wiley: New York, 1995; Chapter 2
3 Eliel, E. L.; Allinger, N. L.; Angyal, S. J. Conformational Analysis; Wiley: New York, 1965
4 Winestein, S.; Holness, N. J. J. Am. Chem. Soc. 1955, 55, 5562
5 Hirsch, J. A. Top Stereochem. 1967, 1, 199   DOI
6 Borsdorf, R.; Kleinpeter, E.; Arnold, M. Z. Chem. 1977, 17, 378
7 Borsdorf, R.; Kleinpeter, E.; Meinel, C.; Lenk, D. Z. Chem. 1978, 18, 185
8 Kleinpeter, E.; Taddei, F. J. Mol. Struct. 2004, 683, 29   DOI   ScienceOn
9 Kleinpeter, E.; Taddei, F.; Wacker, P. Chem. Eur. J. 2003, 9, 1360   DOI   ScienceOn
10 Lewis, B. E.; Schramm, V. L. J. Am. Chem. Soc. 2001, 123, 1327   DOI   ScienceOn
11 Koler, H.; Tschierske, C.; Zaschke, H.; Kleinpeter, E. Tetrahedron 1990, 46, 4241   DOI   ScienceOn
12 Juaristi, E.; Rosquete-Pina, G. A. Pure Appl. Chem. 2003, 75, 589   DOI   ScienceOn
13 Becke, A. D. J. Chem. Phys. 1993, 98, 5648   DOI   ScienceOn
14 Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785   DOI   ScienceOn
15 Salzner, U.; Schleyer, P. V. R. J. Org. Chem. 1994, 59, 2138   DOI   ScienceOn
16 Borsdorf, R.; Muller, R.; Tenner, R.; Kleinpeter, E. Z. Chem. 1976, 16, 106
17 Yeunga, G. F. C.; Setiadia, D. H.; Chass, G. A.; Imre G. C. J. Mol. Struct. (Theochem) 2003, 666-667, 393-396   DOI   ScienceOn
18 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.; Baboul, A. G.; 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN98, Revision A.7; Gaussian: Pittsburgh, PA, 1998
19 Perrin, C. L. Pure Appl. Chem. 1995, 67, 719   DOI   ScienceOn
20 Perrin, C. L.; Fabian, M. A.; Brunckova, J.; Ohta, B. K. J. Am. Chem. Soc. 1999, 121, 6911   DOI   ScienceOn
21 Sakurai, S.; Meinander, N.; Morris, K.; Laane, J. J. Am. Chem. Soc. 1999, 121, 5056   DOI   ScienceOn
22 Omoto, K.; Marusaki, K.; Hirao, H.; Imade, M.; Fujimoto, H. J. Phys. Chem. A 2000, 104, 6499   DOI   ScienceOn
23 Tvaroka, I. J. Phys. Chem. A 2000, 100, 11305
24 Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019, and references therein   DOI   ScienceOn
25 Dabbagh, H. A.; Modarresi-Alam, A.; Tadjarodi, A.; Taeb, A. Tetrahedron 2002, 58, 2621   DOI   ScienceOn
26 Jensen, F. R.; Bushweller, C. H. Adv. Alicycl. Chem. 1971, 3, 139   DOI
27 Wiberg, K. B.; Hammer, J. D.; Castejon, H.; Bailey, W. F.; De Leon, E.; Jarrett, R. M. J. Org. Chem. 1999, 64, 2085   DOI   ScienceOn
28 Tvaroska, I.; André, I.; Carver, J. P. J. Mol. Struct. (Theochem) 1999, 469, 103   DOI   ScienceOn
29 Jiang, Y.; Cole, R. B. J. Am. Soc. Mass. Spectrom. 2005, 16, 60   DOI   ScienceOn
30 Tvaroska, I.; Carver, J. P. Carbohydrate Research, 1998, 309, 1   DOI   ScienceOn
31 Kleinpeter, E.; Taddei, F. J. Mol. Struct. 2002, 585, 223   DOI   ScienceOn