Geometrical Structures and Magnetic Properties of Trinaphtho[ abc,ghi,mno ][18]annulene and its congeners †

Abstract

Pariser–Parr–Pople-type SCF MO and semiempirical magnetic-susceptibility calculations show that trinaphtho[abc,ghi,mno]- and two kinds of triazuleno[abc,ghi,mno][18]annulenes have large diamagnetic susceptibilities and aromatic-islands structures in which three naphthalenes or three azulenes are linked by three olefinic bridges, whereas tripentaleno[abc,ghi,mno]- and triheptaleno[abc,ghi,mno][18]annulenes have small diamagnetic susceptibilities and polyolefine structures where bond alternations are distributed all over their molecular planes.

Keywords

bond alternation magnetic susceptibility [18]Annulene

References

Meier

, Kretzschmann

and Kolshorn

, J. Org. Chem., 1992, 57, 6847.

(a) Kretzschmann

, Müller

, Kolshorn

, Schollmeyer

and Meier

, Chem. Ber., 1994, 127, 1735

Meier

and Müller

, Angew. Chem., 1995, 107, 1598; Angew. Chem. Int. Ed. Engl., 1995, 34, 1437

Müller

, Meier

, Bouas-Laurent

and Desvergne

J. P.

, J. Org. Chem., 1996, 61, 5474

Schnorpfeil

, Meier

and Irie

, Helv. Chim. Acta, 2001, 84, 2467.

(a) Bader

R. F. W.

, Mol. Phys., 1960, 3, 137

Pearson

R. G.

, J. Am. Chem. Soc., 1969, 91, 4947

Bartell

L. S.

, J. Chem. Educ., 1969, 45, 754.

(a) Nakajima

, Fortshr. Chem. Forsch., 1972, 32, 1

10.

Nakajima

, Toyota

and Fujii

, Bull. Chem. Soc. Jpn., 1972, 45, 1022

11.

Kataoka

and Nakajima

, J. Chem. Soc., Perkin Trans. 2, 1986, 1529

12.

Kataoka

, Toyota

and Nakajima

, J. Chem. Soc., Perkin Trans. 2, 1988, 1633

13.

Kataoka

and Toyota

, J. Chem. Res. (S), 1998, 278.

14.

Yamaguchi

and Nakajima

, Bull. Chem. Soc. Jpn., 1974, 47, 1898.

15.

Kataoka

, J. Tohoku Pharmaceutical University, 1999, 46, 219. Since this paper was written in Japanese, it is limited in availability. For comparison, therefore, parts of the results are given in the present paper.