Gas-phase photoelectron spectroscopic and theoretical studies of 1,2- dichalcogenins: Ionization energies, orbital assignments, and an explanation of their color

Journal of the American Chemical Society

Volumn 122, Issue 21, 2000, Pages 5065-5074

  Glass, Richard S ^a   Gruhn, Nadine E ^a   Lichtenberger, Dennis L ^a   Lorance, Edward ^a   Pollard, John R ^a   Birringer, Marc ^b   Block, Eric ^b   Deorazio, Russell ^b   He, Chunhong ^b   Shan, Zhixing ^b   Zhang, Xing ^b  

^a UNIVERSITY OF ARIZONA   (United States)

^b STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHALGONIN; THIARUBRINE A; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CALCULATION; CHEMICAL BINDING; COLOR; DRUG SCREENING; ELECTROCHEMISTRY; SPECTROSCOPY;

EID: 0034738062     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9941330     Document Type: Article

References (35)

1. Bohlmann, F.; Zdero, C. In The Chemistry of Heterocyclic Compounds; Gronowitz, S., Ed.; Wiley: New York, 1985; Vol. 44, Chapter 3.
2. Rodriguez, E. In Biologically Active Natural Products; Cutler, H. G., Ed.; ACS Symposium Series 380; American Chemical Society: Washington, DC, 1988; pp 432-437.
3. Bierer, D. E.; Dener, J. M.; Dubenko, L. G.; Gerber, R. E.; Litvak, J.; Peterli, S.; Peterli-Roth, P.; Truong, T. V.; Mao, G.; Bauer, B. E. J. Med. Chem. 1995, 38, 2628-2648.
4. Borsdorf, R.; Hofmann, H.-J.; Kohler, H.-J.; Scholz, M.; Fabian, J. Tetrahedron 1970, 26, 3227-3231.
5. Fabian, J.; Hartmann, H. Z. Chem. 1978, 18, 145-146.
6. Herndon, W. C.; Parkanyi, C. Tetrahedron 1978, 34, 3419-3425.
7. Fabian, J.; Birner, P. Collect. Czech. Chem. Commun. 1988, 53, 2096-2115.
8. Cimiraglia, R.; Fabian, J.; Hess, B. A., Jr. J. Mol. Struct. (THEOCHEM) 1991, 230, 287-293.
9. Mann, M.; Fabian, J. J. Mol. Struct. (THEOCHEM) 1995, 331, 51-61.
10. Glass, R. S.; Pollard, J. R.; Schroeder, T. B.; Lichtenberger, D. L.; Block, E.; DeOrazio, R.; Guo, C.; Thiruvazhi, M. Phosphorus, Sulfur, Silicon 1997, 120/121, 439-440.
11. Pitchko, V.; Goddard, J. D. Chem. Phys. Lett. 1998, 289, 391-395.
12. Ishida, T.; Oe, S.; Aihara, J. J. Mol. Struct. (THEOCHEM) 1999, 461-462, 553-559.
13. Gillies, J. Z.; Gillies, C. W.; Cotter, E. A.; Block, E.; DeOrazio, R. J. Mol. Spectrosc. 1996, 180, 139-144.
14. Block, E.; Birringer, M.; DeOrazio, R.; Fabian, J.; Glass, R. S.; Guo, C.; He, C.; Lorance, E.; Qian, Q.; Schroeder, T. B.; Shan, Z.; Thiruvazhi, M.; Wilson, G. S.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 5052-5064.
15. Lichtenberger, D. L.; Kellogg, G. E.; Kristofski, J. G.; Page, D.; Turner, S.; Klinger, G.; Lorenzen, J. Rev. Sci. Instrum. 1986, 52, 2366-2366.
16. Westcott, B. L.; Gruhn, N. E.; Enemark, J. H. J. Am. Chem. Soc. 1998, 120, 3382-3386.
17. Turner, D. W.; Baker, C.; Baker, A. D.; Brandle, C. R. Molecular Photoelectron Spectroscopy; Wiley-Interscience: London, 1970.
18. Block, E.; Birringer, M.; He, C. Angew. Chem., Int. Ed. Engl. 1999, 38, 1604-1607.
19. Lichtenberger, D. L.; Copenhaver, A. S. J. Electron Spectrosc. Relat. Phenom. 1990, 50, 335-352.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, B. B.; Stefanov, A.; Nanayakkara, M.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision E.2; Gaussian Inc.: Pittsburgh, PA, 1995.
21. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
22. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135-149.
23. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of He I Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific Societies Press: Tokyo, 1981.
24. Yeh, J. J.; Lindau, I. At. Data Nucl. Data Tables 1985, 32, 1-155.
25. Gelius, U. J. Electron. Spectrosc. Relat. Phenom. 1974, 5, 985-1057.
26. Glass, R. S.; Broeker, J. L.; Jatcko, M. E. Tetrahedron 1989, 45, 1263-1272.
27. Westcott, B. L., Ph.D. Dissertation, The University of Arizona, Tucson AZ, 1997.
28. Bock, H.; Brähler, G.; Dauplaise, D.; Meinwald, J. Chem. Ber. 1981, 114, 2622-2631.
29. Tschmutowa, G.; Bock, H. Z. Naturforsch. 1976, 31B, 1616-1620.
30. Chang, F. C.; Young, V. Y.; Prather, J. W.; Cheng, K. L. J. Electron. Spectrosc. Relat. Phenom. 1986, 40, 363-383.
31. Geometry optimizations were also performed on the first singlet and triplet exeited states of 1,2-dithiin. In these excited states there is a substantial lengthening of the S-S bond length and a lowering of the S-S stretching frequency (see Table 5 in the Supporting Information), which is further proof that the transition in the visible region involves an excited state with significant occupation of a S-S antibonding orbital.
32. Bersuker, I. B. Electronic Structure and Properties of Transition Metal Compounds; John Wiley and Sons: New York, 1996.
33. Percampus, H. H. UV-Vis Atlas of Organic Compounds; VCH: New York, 1992.
34. Nicolaou, K. C.; Defrees, S. A.; Hwang, C. K.; Stylianides, N.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3029-3039.
35. Ishii, A.; Akazawa, T.; Maruta, T.; Nakayama, J.; Hoshino, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 777-779.