Syntheses and structural properties of severely distorted porphyrins: N-methyl derivatives

Heterocycles

Volumn 45, Issue 4, 1997, Pages 651-658

  Clement, Todd E ^a   Nguyen, Liem T ^a   Khoury, Richard G ^a   Nurco, Daniel J ^a   Smith, Kevin M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013083801     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-7754     Document Type: Article

References (12)

1. A. H. Jackson and G. R. Dearden, Ann. N. Y. Acad. Sci., 1973, 206, 151.
2. D. K. Lavallee, 'The Chemistry and Biochemistry of N-Substituted Porphyrins,' VCH, New York, 1987, pp. 1-6.
3. K. M. Barkigia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner, and K. M. Smith, J. Am. Chem. Soc., 1990, 112, 8851.
4. C. J. Medforth, M. O. Senge, K. M. Smith, L. D. Sparks, and J. A. Shelnutt, J. Am. Chem. Soc., 1992, 114, 9859, and references cited therein.
5. a) K. M. Barkigia, L. Chantranupong, K. M. Smith, and J. Fajer, J. Am. Chem. Soc., 1988, 110, 7566;
6. b) C. J. Medforth, M. D. Berber, K. M. Smith, and J. A. Shelnutt, Tetrahedron Lett., 1990, 31, 3719;
7. M. O. Senge, T. Ema, and K. M. Smith, J. Chem. Soc., Chem. Commun., 1995, 733.
8. a) D. K. Lavallee, 'The Chemistry and Biochemistry of N-Substituted Porphyrins,' VCH, New York, 1987, pp. 7-39;
9. b) M. O. Senge, T. P. Forsyth, L. T. Nguyen, and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1994, 33, 2485.
10. T. P. Wijesekera, J. B. Paine III, D. Dolphin, F. W. B. Einstein, and T. Jones, J. Am. Chem. Soc., 1983, 105, 6747.
11. For a preliminary study of N-methylation of highly distorted porphyrins, see M. D. Berber de Jiminez, 'Ph.D. Dissertation', University of California, Davis, 1990. pp. 150-154.
12. -1). Hydrogen atom positions were generated by their idealized geometry and refined using a riding model. One of the iodine anions was disordered over two half occupied sites. All non-hydrogen atoms were refined with anisotropic thermal parameters. The final structure had 745 parameters with R 1 = 0.069 and wR2 = 0.211.