Crystal engineering using anilic acids and dipyridyl compounds through a new supramolecular synthon

被引:78
作者
Zaman, MB
Tomura, M [1 ]
Yamashita, Y
机构
[1] Inst Mol Sci, Okazaki, Aichi 4448585, Japan
[2] Tokyo Inst Technol, Dept Elect Chem, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268502, Japan
[3] Univ Dhaka, Dept Appl Chem & Chem Technol, Dhaka 1000, Bangladesh
关键词
D O I
10.1021/jo001746i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anilic acids, 2,5-dihydroxy-1,4-benzoquinone (1a), 2,5-dibromo-3,6-dihydroxy-1,4-benzoquinone (bromanilic acid; 1b), 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid; 1c), and 2,5-dicyano-3,6-dihydroxy-1,4-benzoquinone (cyananilic acid; 1d), were cocrystallized with rigid organic ligands containing two pyridine rings, 2,4-bipyridine (2a), 4,4 ' -bipyridine (2b), 1,2-bis(2-pyridyl)ethylene (3a), 1,2-bis(4-pyridyl)ethylene (3b), 2,2 ' -dipyridylacetylene (4a), 3,3 ' -dipyridylacetylene (4b), and 4,4 ' -dipyridylacetylene (4c). Fourteen complexes 5-18 were obtained as single crystals, and their crystal structures were successfully determined by X-ray analysis. All complexes except those with 2a are 1:1 and are composed of an infinite linear or zigzag tape structure, the formation of which is ascribed to intermolecular O-H . . .N, N+-H . . .O, or N+-H . . .O- hydrogen bonds or a combination of these between the anilic acids and the dipyridyl compounds. In the complexes 5 and 6, no infinite tape structure is observed although the molecular units connected by a similar hydrogen-bonding pattern are formed. For the 1:1 complexes, we have found two types of stacking arrangements, segregated stacks (7, 9, 12-15, 18) and alternated ones (8, 10, 11, 16, 17). In the complexes of 1c with the series of dipyridylacetylenes 4 (14, 15, 17), the neutral, dication, and monocaction states are formed depending on the nitrogen positions, which can be attributed to the different basicity of the pyridyl groups.
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页码:5987 / 5995
页数:9
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