Thieno[3,4-f]isothianaphthene and its N -substitutes: A theoretical insight

Molecular Simulation

Volumn 32, Issue 6, 2006, Pages 457-464

  Shen, W ^a   Li, M ^b   Huang, H ^b   Li, Y ^b   Wang, S ^b  

^a SICHUAN UNIVERSITY   (China)

^b SOUTHWEST UNIVERSITY   (China)

Author keywords

DFT; Electronic structure; N substitutes; Nonclassical structure; Thieno 3,4 f isothianaphthene

Indexed keywords

CONDUCTIVE PLASTICS; ELECTRONIC STRUCTURE; GEOMETRY; IONIZATION; PROBABILITY DENSITY FUNCTION;

N-SUBSTITUTES; NONCLASSICAL STRUCTURES; SPLITTING ENERGIES; THIENO[3,4-F]ISOTHIANAPHTHENE;

AROMATIC COMPOUNDS;

EID: 33748560133     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020600863014     Document Type: Article

References (32)

1. M.P. Cava, N.M. Pollack, G.A. Dieterle. Nonclassical condensed thiophenes. I. 1,3-Disubstituted thieno[3,4-c]thiophenes. J. Am. Chem. Soc., 95, 2558 (1973).
2. K.T. Potts, D. Mckeough. Synthesis of nonclassical thiophenes. J. Am. Chem. Soc., 96, 4268 (1974).
3. R. Gleiter, R. Bartetzko, G. Brähler, H. Bock. Electronic structure of sulfur compounds. 28. Radical ions. 24. Electronic structure of tetraphenylthieno[3,4-c]thiophene. Photoelectron, electron spin resonance, and electronic absorption spectra. J. Org. Chem., 43, 3893 (1978).
4. K.J. Miller, K.F. Moschner, K.T. Potts. Theoretical study of thieno[3,4-c]thiophene, a nonclassical thiophene system. J. Am. Chem. Soc., 105, 1705 (1983).
5. 2-Sulfur heterocycles. An ah initio and density functional study. J. Org. Chem., 62, 1766 (1997).
6. V. Schomaker, L. Pauling. The electron diffraction investigation of the structure of benzene, pyridine, pyrazine, butadiene-1,3, cyclopentadiene, furan, pyrrole, and thiophene. J. Am. Chem. Soc., 61, 1769 (1939).
7. M.P. Cava, N.M. Pollack. Reactive tetravalent sulfur intermediates. Nonclassical thiophthene. J. Am. Chem. Soc., 89, 3639 (1967).
8. M.P. Cava, G.M.E. Husbands. Tetraphenylthieno[3,4-c]thiophene. A stable nonclassical thiophene. J. Am. Chem. Soc., 91, 3952 (1969).
9. A. Ishii, J. Nakayama, J. Kazami, Y. Ida, T. Nakamura, M. Hoshino. Synthesis and reactions of 1,3,4,6-tetra-2-thienylthieno[3,4-c]thiophene. J. Org. Chem., 56, 78 (1991).
10. T. Kobayashi, K. Ozaki, S. Yoneda. Electronic structure of tetrakis(isopropylthio)thieno[3,4-c]thiophene studied by photoelectron and electronic absorption spectroscopies combined with MO calculations. J. Am. Chem. Soc., 110, 1793 (1988).
11. H.C. Brown, B.T. Cho, W.S. Park. Chiral synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-0-(1,2:5,6-di-O-isopropylidene-.alpha-D-glucofuranosyl) -9-boratabicyclo[3.3.1] nonane. J. Org. Chem., 53, 1231 (1988).
12. A. Mangini, C. Zauli. Calculation of some π-electron states in furan, thiophen, and the parent hydrocarbon compound using valence-bond approximation. J. Chem. Soc., 2210 (1960).
13. D.T. Clark. A self consistent field molecular orbital treatment of the reactivity of thiophene and the isomeric thienothiophenes. Tetrahedron, 24, 2663 (1968).
14. J. Cioslowski, P.R. Surjan. An observable-based interpretation of electronic wavefunctions: application to "hypervalent" molecules. J. Mol. Struct. (THEOCHEM), 255, 9 (1992).
15. M. Mann, J. Fabian. Structures and properties of 1,2-dithiolylium-4- methide, 1,2-dithiolylium-4-olate and 1,2-dithiolylium-4-thiolate: an MO study at the HF and post-HF levels. J. Phys. Org. Chem., 8, 536 (1995).
16. R. Gleiter, R. Bartetzko, G. Brähler, H. Bock. Electronic structrue of tetraphenylthieno[3,4-c]thiophene. Photoelectron, electron spin resonance, and electronic absorption spectra. J. Org. Chem.., 43, 3893 (1978).
17. M. Tachibana, S. Tanaka, Y. Yamashita, K. Yoshizaw. Small band-gap polymers involving tricyclic nonclassical thiophene as a building block. J. Phys. Chem. B, 106, 3549 (2002).
18. R.G. Parr, W. Yang. Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York (1989).
19. A.D. Becke. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys., 98, 5648 (1993).
20. C. Lee, W. Yang, R.G. Parr. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 37, 785 (1988).
21. D.E. Woon, T.H. Dunning. Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon. J. Chem. Phys., 98, 1358 (1993).
22. J.E. Carpenter, F. Weinhold. Analysis of the geometry of the hydroxymethyl radical by the "different hybrids for different spins" natural bond orbital procedure. J. Mol. Struct. (THEOCHEM), 169, 41 (1988).
23. A.E. Reed, L.A. Curtiss, F. Weinhold. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev., 88, 899 (1988).
24. J.P. Foster, F. Weinhold. Natural hybrid orbitals. J. Am. Chem. Soc., 102, 7211 (1980).
25. A.E. Reed, R.B. Weinstock, F. Weinhold. Natural population analysis. J. Chem. Phys., 83, 735 (1985).
26. P.v.R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, NJ.R.v. Hommes. Nucleus-independent chemical shifts: a simple and efficient aromaticity probe. J. Am. Chem. Soc., 118, 6317 (1996).
27. R.F.W. Bader. Atoms in Molecules, A Quantum Theory; International Series of Monographs in Chemistry, 22, Oxford University Press, Oxford, UK (1990).
28. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., 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, 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.C. 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. AlLaham, 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 A.1, Gaussian, Inc., Pittsburgh PA (2003).
29. F. Biegler-König, J. Schönbohm, R. Derdau, D. Bayles, F.W. AIM2000, version2.0, McMaster University Bader (2002).
30. V.I. Minkin, M.N. Glukhovtsev, B.Y. Simkin. Aromaticity and Antiammaticity, Wiley, New York (2002).
31. P.J. Garratt. Aromaticity, Wiley, New York (1986).
32. J.A. Eluidge, L.M. Jackman. Studies of aromaticity by nuclear magnetic resonance spectroscopy. Part I. 2-Pyridones and related systems. J. Chem. Soc., 859 (1961).