Conformation and absolute configuration of 11,12-cyclopropyl retinal analogs - An RHF/DFT/CIS study

Journal of Molecular Modeling

Volumn 7, Issue 5, 2001, Pages 132-139

  Kampermann, Hermann ^a   Kolster, Klaus ^a   Buss, Volker ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

Ab initio calculations; Gaussian CIS; Retinal; Retinal analogs

Indexed keywords

CYCLOPROPANE DERIVATIVE; METHYL GROUP; RETINAL; RETINOID DERIVATIVE; RHODOPSIN; SCHIFF BASE;

ARTICLE; CIRCULAR DICHROISM; CIS TRANS ISOMERISM; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG CONFORMATION; ENERGY; GEOMETRY; HUMAN; MATHEMATICAL COMPUTING; MOLECULAR INTERACTION; PRIORITY JOURNAL; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0035789393     PISSN: 16102940     EISSN: None     Source Type: Journal    
DOI: 10.1007/S008940100020     Document Type: Article

References (20)

1. Wald, G. Science 1968, 162, 230.
2. Nakanishi, K.; Crouch, R. Isr. J. Chem. 1995, 35, 253.
3. Akita, H.; Tanis, S. P.; Adams, M.; Balogh-Nair, V.; Nakanishi, K. J. Am. Chem. Soc. 1980, 102, 6372.
4. Lou, J.; Hashimoto, M.; Berova, N.; Nakanishi, K. Org. Lett. 1999, 1, 51.
5. Tan, Q.; Lou, J.; Borhan, B.; Karnaukhova, E.; Berova, N.; Nakanishi, K. Angew. Chem. 1997, 109, 2190; Angew. Chem. Int. Ed. Engl. 1997, 36, 2089.
6. Buss, V.; Kolster, K.; Terstegen, F.; Vahrenhorst, R. Angew. Chem. 1998, 110, 1997; Angew. Chem. Int. Ed. Engl. 1998, 37, 1893.
7. 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,; Petersson, J. 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.; 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.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.5; Gaussian: Pittsburgh, PA, 1998.
8. Greenberg, A.; Stevenson, T. A. In Molecular Structure and Energetics; Liebman, J.F., Greenberg, A., Eds.; VCH: New York, 1986; Vol. 3, p 193.
9. Schleyer, P. v. R.; Buss, V. J. Am. Chem. Soc. 1969, 91, 5880.
10. DeMeijere, A.; Lüttke, A. Tetrahedron 1969, 25, 2047.
11. Skancke, A.; Boggs, J. E. J. Mol. Struct. 1979, 51, 267.
12. Volltrauer, H. N.; Schwendeman, R. H. J. Chem. Phys. 1971, 54, 260.
13. De Mare, G. R.; Peterson, M. R. J. Mol. Struct. 1983, 104, 115.
14. Hoffmann, R. Tetrahedron Lett. 1970, 2907.
15. Bocian, D. F.; Strauss, H. L. J. Am. Chem. Soc. 1977, 99, 2866.
16. Bocian, D. F.; Strauss, H. L. J. Am. Chem. Soc. 1977, 99, 2876.
17. Buss, V. Chirality 2001, 13, 13.
18. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy. Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
19. Rao, C. N. R. Ultra-Violet and Visible Spectroscopy; Butterworths: London, 1975; p 51.
20. Czikkely, V.; Försterling, H.-D.; Kuhn, H. Chem. Phys.Lett. 1970, 6, 207.