Vibrational and electronic circular dichroism of dimethyl mesobilirubins-XIIIα

Journal of Physical Chemistry B

Volumn 116, Issue 19, 2012, Pages 5628-5636

  Abbate, Sergio ^a   Lebon, France ^a   Longhi, Giovanna ^a   Boiadjiev, Stefan E ^b   Lightner, David A ^c  

^a UNIVERSITY OF BRESCIA   (Italy)

^b MEDICAL UNIVERSITY PLEVEN   (Bulgaria)

^c UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DENSITY FUNCTIONAL THEORY; DICHROISM;

AB INITIO DENSITY FUNCTIONAL THEORIES (DFT); ASSIGNMENT OF; CONFORMATIONAL PROPERTIES; ELECTRONIC CIRCULAR DICHROISM; EXCITON MODELS; OBSERVED DATA; SOLVENT MOLECULES; TIME-DEPENDENT DFT; VIBRATIONAL ABSORPTION; VIBRATIONAL CIRCULAR DICHROISM SPECTRUM; VIBRATIONAL NORMAL MODES;

CALCULATIONS;

BILIRUBIN; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; COMPARATIVE STUDY; CONFORMATION; ELECTRONICS; HYDROGEN BOND; INFRARED RADIATION; SOLUTION AND SOLUBILITY; TIME; VIBRATION;

BILIRUBIN; CIRCULAR DICHROISM; ELECTRONICS; HYDROGEN BONDING; INFRARED RAYS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SOLUTIONS; SOLVENTS; TIME FACTORS; VIBRATION;

EID: 84862061532     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp3013255     Document Type: Article

References (44)

1. Mc Donagh, A. F. Bile Pigments: Bilatrienes and 5,15-Biladienes. In The Porphyrins; Dolphin, D., Ed; Academic Press: New York, 1979; Vol. 6, p 293.
2. Schmid, R.; McDonagh, A. F. Hyperbilirubinemia. In The Metabolic Basis for Inherited Diseases; Stanbury, J. B., Wyngaorder, J. B., Frederickson, D. S., Eds.; McGraw-Hill: New York, 1978; pp 1221-1257.
3. Bonnett, R.; Davies, J. E.; Hursthouse, M. B.; Sheldrick, G. M. Proc. R. Soc. London B 1978, 202, 249-268
4. LeBas, C.; Allegret, A.; Mauguen, Y.; De Rango, C; Bailly, M. Acta Crystallogr. B 1980, B36, 3007-3011
5. Kaplan, D.; Navon, G. Israel J. Chem 1983, 23, 177-186
6. Dörner, T.; Knipp, B.; Lightner, D. A. Tetrahedron 1997, 53, 2697-2716
7. Berova, N.; Nakanishi, K. Exciton Chirality Methods: Principles and Applications. In Circular Dichroism: Principles and Applications, 2 nd ed.; Berova, N.; Nakanishi, K.; Woody, R. A., Eds.; Wiley-VCH: New York, 2000.
8. Person, R. V.; Peterson, B. R.; Lightner, D. A. J. Am. Chem. Soc. 1994, 116, 42-59
9. Boiadjiev, S. E.; Lightner, D. A. J. Am. Chem. Soc. 2000, 122, 378-383
10. Boiadjiev, S. E.; Lightner, D. A. Chirality 2001, 13, 251-257
11. Stephens, P. J. In Computational Medicinal Chemistry for Drug Discovery; Bultinck, P.; de Winter, H.; Langenaecker, W.; Tollenaere, J., Eds.; Marcel Dekker: New York, 2003; Chapter 26, pp 699-725.
12. Stephens, P. J.; Devlin, F. J.; Pan, J. J. Chirality 2008, 20, 643-663
13. Nafie, L. A.; Freedman, T. B. In Circular Dichroism: Principles and Applications; Nakanishi, K.; Berova, N.; Woody, R. W., Eds.; Wiley-VCH: New York, 2000; Chapter 4, pp 97-132.
14. Keiderling, T. A. In Circular Dichroism: Principles and Applications; Nakanishi, K.; Berova, N.; Woody, R. W., Eds.; Wiley-VCH: New York, 2000; Chapter 22, pp 621-666.
15. Polavarapu, P. L.; Zhao, C. Fresenius' J. Anal. Chem. 2000, 366, 727-734
16. Stephens, P. J. J. Phys. Chem. 1985, 89, 748-751
17. Stephens, P. J.; Lowe, M. A. Annu. Rev. Phys. Chem. 1985, 36, 213
18. Buckingham, A. D.; Fowler, P. W.; Galwas, P. A. Chem. Phys. 1987, 112, 1
19. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. A 1994, 98, 11623
20. Cheeseman, J. R.; Devlin, F. J.; Frisch, M. J.; Stephens, P. J. Chem. Phys. Lett. 1996, 252, 211
21. Stephens, P. J.; Ashvar, C. S.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. Mol. Phys. 1996, 89, 579-594
22. Nicu, V. P.; Neugebauer, J.; Wolff, S. K.; Baerends, E. J. Theor. Chem. Acc. 2008, 119, 245-263
23. Andrushchenko, V.; Bouř, P. Chirality 2010, 22, E96-E114
24. Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Smith, A. B., III. J. Nat. Prod. 2006, 69, 1055-1064
25. Bergueño-Tapia, E.; Joseph-Nathan, P. Phytochemistry 2008, 69, 2251-2256
26. Abbate, S.; Ciogli, A.; Fioravanti, S.; Gasparrini, F.; Longhi, G.; Pellacani, L.; Rizzato, E.; Spinelli, D.; Tardella, P. A. Eur. J. Org. Chem. 2010, 6193-6199
27. Abbate, S.; Burgi, L. F.; Castglioni, E.; Lebon, F.; Longhi, G.; Toscano, E.; Caccamese, S. Chirality 2009, 21, 436-441
28. Goncharova, I.; Urbanová, M. Tetrahedron: Asymmetry 2007, 18, 2061-2068
29. Goncharova, I.; Urbanová, M. Anal. Bioanal. Chem. 2008, 392, 355-1365
30. Goncharova, I.; Urbanová, M. Anal. Biochem. 2009, 392, 28-36
31. Alagona, G.; Ghio, C.; Monti, S. Phys. Chem. Chem. Phys. 2000, 2, 4884-4890
32. Granucci, G.; Mazzoni, M.; Persico, M.; Toniolo, A. Phys. Chem. Chem. Phys. 2005, 7, 2594-2598
33. Metzroth, T.; Lenhart, M.; Gauss, J. Appl. Magn. Reson. 2008, 33, 457-467
34. Boiadjiev, S. E.; Person, R. V.; Puzicha, G.; Knobler, C.; Maverick, E.; Trueblood, K. N.; Lightner, D. A. J. Am. Chem. Soc. 1992, 114, 10123-10133
35. Puzicha, G.; Pu, Y.-M; Lightner, D. A. J. Am. Chem. Soc. 1991, 113, 3583-3592
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C; Jaramillo, J.; Gomperts, R. E.; Stratmann, O.; Yazyev, A. J.; Austin, R.; Cammi, C.; Pomelli, J. W.; Ochterski, R.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Pittsburgh, PA, 2009.
37. Brower, J. O.; Huggins, M. T.; Boiadjiev, S. E.; Lightner, D. A. Monatsh. Chem. 2000, 131, 1047-1053
38. Boiadjiev, S. E.; Lightner, D. A. J. Heterocyclic Chem. 2000, 37, 863-870
39. Furche, F.; Ahlrichs, R.; Wachsmann, C.; Weber, E.; Sobank, A.; Vögtle, F.; Grimme, S. J. Am. Chem. Soc. 2000, 122, 1717-1724
40. Yamay, T.; Taw, D. P.; Handy, N. Chem. Phys. Lett. 2004, 393, 51-57
41. Bauman, D.; Killet, C.; Boiadjiev, S. E.; Lightner, D. A.; Schönhofer, A.; Kuball, H. G. J. Phys. Chem. 1996, 100, 11546-11558
42. Kaplan, D.; Navon, G. Biochem. J. 1982, 201, 605-613
43. Zhang, P.; Polavarapu, P. L. J. Phys. Chem. A 2007, 111, 858-871
44. Yang, B.; Taylor, R. C.; Morris, M. D.; Wang, X.-Z.; Wu, J.-G.; Yu, B.-Z.; Xu, G.-X.; Soloway, R. D. Spectrochim. Acta 1993, 49A, 1733-1749