Stacking Geometry of 5, 10, 15, 20-Tetramethylporphyrinatonickel (II) by a Modified MM2 Method

Mayumi Kamishima; Masaaki Kojima; Yuzo Yoshikawa

doi:10.14827/jccj1999.13.29

Mayumi Kamishima, Masaaki Kojima, Yuzo Yoshikawa

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JOURNAL FREE ACCESS

2001 Volume 13 Issue 1 Pages 29-36

DOI https://doi.org/10.14827/jccj1999.13.29

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Published: March 31, 2001 Received: November 17, 2000 Available on J-STAGE: August 13, 2009 Accepted: December 28, 2000 Advance online publication: - Revised: -
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Date of correction: August 13, 2009 Reason for correction: - Correction: CITATION Details: Wrong : 1 For example : (a) T. Benzing, T. Tjivikua, J. Wolfe, J. Rebek Jr., Science 242,266 (1988). (b) A. V. Muehldorf, D. Van Engen, J. C. Warner, A. D. Hamilton, J. Am. Chem. Soc., 110, 6561 (1988). (c) J.-M. Lehn, F. Schmidt, J -P. Vigneron, Tetrahedron Lett., 29, 5255 (1988). (d) S. C. Zimmerman, W. Wu, J. Am. Chem. Soc., 111, 8054 (1989).
2 (a) S. K. Burley, G. A. Petsko, Science, 229, 23 (1985). (b) J. Singh, J. M. Thornton, FEBS Lett., 191, 1 (1985).
3 W. Saenger, Principles of Nucleic Acid Structure, Springer-Verlag, New York, (1984).
4 S. Tsuzuki, T. Uchimaru, K. Matsumura, M. Mikami, K. Tanabe, Chem. Phys. Lett., 319,547 (2000).
5 C. H. Hunter, J. K. M. Sanders, J. Am. Chem. Soc., 112, 5525 (1990).
6 M. Rubio, F. Torrens, J. Sánchez-MarÍn. J. Comput. Chem., 14,647 (1993).
7 P. Hobza and V. &Scaron;pirko, J. Phys. Chem. A., 102, 2501 (1998).
8 S. L. Price and A. Stone, J. Chem. Phys., 86, 2859, (1987).
9 (a) Y. Yoshikawa, Chem. Lett., 1385 (1980). (b) Y. Yoshikawa, J. Comput. Chem., 11,326 (1990).
10 For example : (a) M. Murata, M. Kojima, A. Hioki, M. Miyagawa, M. Hirotsu, K. Nakajima, M. Kita, S. Kashino, Y. Yoshikawa, Coord. Chem. Rev., 174,109 (1998). (b) M. Goto, M. Sumimoto, T. Matsumoto, M. Iwasaki, Y. Tanaka, H. Kurosaki, K. Yuto, Y. Yoshikawa, Bull. Chem. Soc. Jpn., 73, 1589 (2000).
11 J. C. Gallucci, P. N. Swepston, and J. A. Ibers, Acta Crystallogr., Sect B, 38, 2134 (1982).
12 F. W. Kutzler, P. N. Swepston, Z. Berkovitch-Yellin, D. E. Ellis, and J. A. Ibers, J. Am. Chem. Soc., 105, 2996 (1983).
13 B. M. Chen and A. Tulinsky, J. Am. Chem. Soc., 94, 4144 (1972).
14 The parameters for the [Ni (tmp)] complex are available from the authors upon request.
15 ZINDO (CAChe version 3.8), CAChe Scientific, 1995. The calculations were carried out on a Power Macintosh 8100/100 (Apple).
16 M. Kamishima, M. Kojima, and Y. Yoshikawa, J. Comput. Chem., in press.

Right : 1 For example : (a) T. Benzing, T. Tjivikua, J. Wolfe, J. Rebek Jr., Science 242,266 (1988). (b) A. V. Muehldorf, D. Van Engen, J. C. Warner, A. D. Hamilton, J. Am. Chem. Soc., 110, 6561 (1988). (c) J.-M. Lehn, F. Schmidt, J -P. Vigneron, Tetrahedron Lett., 29, 5255 (1988). (d) S. C. Zimmerman, W. Wu, J. Am. Chem. Soc., 111, 8054 (1989).
2 (a) S. K. Burley, G. A. Petsko, Science, 229, 23 (1985). (b) J. Singh, J. M. Thornton, FEBS Lett., 191, 1 (1985).
3 W. Saenger, Principles of Nucleic Acid Structure, Springer-Verlag, New York, (1984).
4 S. Tsuzuki, T. Uchimaru, K. Matsumura, M. Mikami, K. Tanabe, Chem. Phys. Lett., 319,547 (2000).
5 C. H. Hunter, J. K. M. Sanders, J. Am. Chem. Soc., 112, 5525 (1990).
6 M. Rubio, F. Torrens, J. Sánchez-MarÍn. J. Comput. Chem., 14,647 (1993).
7 P. Hobza and V. Špirko, J. Phys. Chem. A., 102, 2501 (1998).
8 S. L. Price and A. Stone, J. Chem. Phys., 86, 2859, (1987).
9 (a) Y. Yoshikawa, Chem. Lett., 1385 (1980). (b) Y. Yoshikawa, J. Comput. Chem., 11,326 (1990).
10 For example : (a) M. Murata, M. Kojima, A. Hioki, M. Miyagawa, M. Hirotsu, K. Nakajima, M. Kita, S. Kashino, Y. Yoshikawa, Coord. Chem. Rev., 174,109 (1998). (b) M. Goto, M. Sumimoto, T. Matsumoto, M. Iwasaki, Y. Tanaka, H. Kurosaki, K. Yuto, Y. Yoshikawa, Bull. Chem. Soc. Jpn., 73, 1589 (2000).
11 J. C. Gallucci, P. N. Swepston, and J. A. Ibers, Acta Crystallogr., Sect B, 38, 2134 (1982).
12 F. W. Kutzler, P. N. Swepston, Z. Berkovitch-Yellin, D. E. Ellis, and J. A. Ibers, J. Am. Chem. Soc., 105, 2996 (1983).
13 B. M. Chen and A. Tulinsky, J. Am. Chem. Soc., 94, 4144 (1972).
14 The parameters for the [Ni (tmp)] complex are available from the authors upon request.
15 ZINDO (CAChe version 3.8), CAChe Scientific, 1995. The calculations were carried out on a Power Macintosh 8100/100 (Apple).
16 M. Kamishima, M. Kojima, and Y. Yoshikawa, J. Comput. Chem., in press.

Abstract

The stacking interaction of 5, 10, 15, 20-tetramethylporphyrinatonickel (II) was calculated as a trimer by the molecular mechanics version 2 using both the point-charge model and the three-center charge model. The stacking structure for the complex was reproduced fairly well by both methods; the obtained structures are roughly in agreement with the crystal structure. By using the three-center charge model, the minimum displaced distance between each stacking molecule was consistent with the X-ray structures. On the other hand, the distance obtained from the method using the point-charge model was slightly longer. The obtained Ni—N bonds by both methods were considerably longer compared with the X-ray results. The factor for this elongation is discussed.

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