Monitoring structural transformations in crystals. 6. The [4 + 4] photodimerization of 9-methylanthracene

二聚体 单体 分子 环戊酮 化学 结晶学 Crystal(编程语言) 晶体结构 光化学 催化作用 有机化学 聚合物 计算机科学 程序设计语言
作者
Ilona Turowska‐Tyrk,Elżbieta Trzop
出处
期刊:Acta crystallographica [Wiley]
卷期号:59 (6): 779-786 被引量:45
标识
DOI:10.1107/s0108768103023255
摘要

The structural changes in a crystal of 9-methylanthracene (1) during the [4 + 4] photodimerization were monitored by means of X-ray diffraction. This is the first example in the literature of such a study of a [4 + 4] photodimerization. The results obtained were compared with data for the [2 + 2] photodimerization. The shape of the product molecules and their preferred packing can explain the crystal disintegration. This was the reason that the reaction was monitored only to 28% completion. As far as could be determined the reaction proceeds with a constant rate. The cell volume increases at the beginning of the transformation and decreases afterwards. The product molecules do not assume a fixed position in the crystal during the photo-reaction, but move in a smooth way that includes a rotational component. The movements of the reactant are much smaller. Movements of molecules characterized by a rotational component were also observed in the case of the [2 + 2] photodimerization of 5-benzylidene-2-benzylcyclopentanone and 5-benzylidene-2-(4-chlorobenzyl)-cyclopentanone. The distance between the reacting atoms of the adjacent monomer molecules of (1) decreases with the degree of reaction completion, but more slowly than in the case of the [2 + 2] photodimerizations cited above. The orientation of the neighbouring monomer molecules changes during the phototransformation so that the monomer pair resembles the dimer product.

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