Conformational behaviors of trans-2,3-bis(methylthio)-1,4-dioxane, -dithiane and –diselenane. A hybrid-DFT study and NBO interpretations
Subject Areas : Journal of the Iranian Chemical ResearchDavood Nori-Shargh 1 , Zahra Mahmoodi 2 , Nasrin Masnabadi 3 , Hooriye Yahyaei 4 , Seiedeh Negar Mousavi 5
1 - Department of Chemistry, Science Faculty, Arak Branch, Islamic Azad University, Arak, Iran
2 - Department of Chemistry, Science Faculty, Arak Branch, Islamic Azad University, Arak, Iran
3 - Department of Chemistry, Roudehen Branch, Islamic Azad University, Roudehen, Iran
4 - Department of Chemistry, Islamic Azad University, Zanjan Branch, P.O.Box 49195.467,Zanjan, Iran
5 - Department of Chemistry, Science Faculty, Arak Branch, Islamic Azad University, Arak, Iran
Keywords:
Abstract :
[1] U. Lemieux, S. Koto, Tetrahedron 30 (1974) 1933-1944.
[2] T. Edwards, Chem. Ind. (London) (1955) 1102-1111.
[3] E. Juaristi, G. Cuevas, The Anomeric Effect, CRC Press. Inc., Florida, 1995.
[4] C. Altona, C. Romers, E. Havinga, Tetrahedron Lett. 21 (1959) 16-20.
[5] N.D. Epiotis, R.L. Yates, R.J. Larson, C.R. Kirmayer, F. Bernardi, J. Am. Chem. Soc. 99 (1977)
8379-8388.
[6] E.L. Eliel, S.H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
[7] J.P. Praly, R.U. Lemieux, Can. J. Chem. 65 (1987) 213-223.
[8] M.A. Pericás, A. Riera, J. Guilera, Tetrahedron 42 (1986) 2717-2718.
[9] N.S. Zefirof, L.G. Gurvich, A.S. Shashkov, M.Z. Krimer, E.A. Vorob’eva, Tetrahedron 32 (1976)
1211-1219.
[10] E.L. Eliel, E. Juaristi, J. Am. Chem. Soc. 100 (1978) 6114-6119.
[11] E. Juaristi, J. Chem. Edu. 56 (1979) 438-441.
[12] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A.
Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone,
B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K.
Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene,
X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E.
Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K.
Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels,
M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q.
Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I.
Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M.
Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian
03, Revision B.03, Gaussian, Inc., Wallingford CT, 2004.
[13] A.D. Becke, J. Chem. Phys. 98 (1993) 5648-5652.
[14] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785-789.
[15] W.J. Hehre, L. Radom, P.V.R. Schleyer, J.A. Pople, Ab initio Molecular Orbital Theory Wiley, New
York, 1986.
[16] J.M. Seminario, P. Politzer, (Eds), Modern Density Function Theory, A Tool for Chemistry,
Elsevier, Amsterdam, 1995.
[17] E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, J.A. Bohmann, C.M. Morales, F.
Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2004. NBO
Version 5.G.
[18] F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 7 (2005) 3297-3305.
[19] D. Nori-Shargh, F. Roohi, F. Deyhimi, R. Naeem-Abyaneh, J. Mol. Struct. (Theochem) 763 (2006)
21-28.
D. Nori-Shargh & et al. / J. Iran. Chem. Res. 3 (2010) 179-189
189
[20] D. Nori-Shargh, M. Malekhosseini, F. Deyhimi, J. Mol. Struct. (Theochem) 763 (2006) 187-198.
[21] D. Nori-Shargh, F. Deyhimi, J.E. Boggs, S. Jameh-Bozorghi, R. Shakibazadeh, J. Phys. Org. Chem.
20 (2007) 355-364.
[22] D. Nori-Shargh, H. Yahyaei, J. Mol. Struct. (Theochem) 913 (2009) 8-15.
[23] D. Nori-Shargh, N. Hassanzadeh, M. Kosari, S. Sharifi, J. Mol. Struct. (Theochem) 940 (2010) 129-
134.
[24] A. Zeinalinezhad, D. Nori-Shargh, Z. Abbasi-Bakhtiari, J.E. Boggs, J. Mol. Struct. (Theochem) 947
(2010) 52-57.
[25] D. Nori-Shargh, H. Yahyaei, J.E. Boggs, J. Mol. Graph. Model. 28 (2010) 807-813.
[26] K.B. Wiberg, M.A. Murcko, J. Phys. Chem. 91 (1987) 3616-3620.
[27] F. Freeman, A. Phornvoranunt, W.J. Hehre, J. Phys. Org. Chem. 11 (1998) 831-835.
[28] T.M. Gilbert, Tetrahedron Lett. 39 (1998) 9147-9150.
[29] M. Remko, P.D. Lyne, W.G. Richards, Phys. Chem. Chem. Phys. 1 (1999) 5353-5357.
[30] D. Strickland, R.A. Caldwell, J. Phys. Chem. 97 (1993) 13394-13402.
[31] I. Arnason, G.K. Thorarinson, E. Matern, J. Mol. Struct. (Theochem) 545 (1998) 91-102.