APPLICATION OF THE OCTET THEORY TO SINGLE-RING AROMATIC COMPOUNDS
APPLICATION OF THE OCTET THEORY TO SINGLE-RING AROMATIC COMPOUNDS
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八位组理论在单环芳香族化合物中的应用
DOI：
10.1021/ja01429a002
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发表时间：
1922
影响因子：
15
通讯作者：
E. C. Crocker
中科院分区：
文献类型：
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作者：
E. C. Crocker
I.苯介绍。原子结构的“八隅体”或“路易斯-朗缪尔”理论[1]在阐明我们对无机化合物的一般观点方面起了很大作用。它已成功地应用于某些含氮的有机化合物，2应用于某些较简单的烃类，最近还应用于酮类的加成化合物，3但迄今为止，它还没有应用于芳香族化合物结构的复杂问题。立方体似乎是对于8个相互排斥的电子来说必须是最稳定的形式。这种立方八隅体，作为第一种近似，具有很大的价值，因为它清楚地表明了两种不同类型的化合物：共享的电子对或非极性“键”，以及完整的带电八隅体或八隅体与氢核之间的静电吸引，我们认为这是离子化合物。它还清楚地表明，“五价”氮没有5个有机类型的键。除了旧的化合价理论之外，当时还没有人认识到碳、氢和氧对有机化合物的影响。此外，碳的立方体形式与光学活性不相容，光学活性要求原子基本上是四面体的。正如刘易斯最近所说的那样，他的第一篇论文还没有发表，他就断定八隅体可能是四面体而不是立方体。然而，这种四面体类型要求电子或多或少成对存在，这种排列显然与它们带电不一致。帕森斯的磁子理论，其中他认为电子是单位磁系统以及单位的负
I. Benzene Introduction.—The “octet” or“Lewis-Langmuir” theory1of atomic structure has done much to clarify our views concerning inorganic com-pounds in general. It has been applied with conspicuous success to some of the organic compounds ofnitrogen, 2 to some of the simpler hydrocar-bons, and more recently, to addition compoundsof ketones, 3 yet upto thepresent, it has not been applied to theperplexing problem of the struc-ture of aromatic compounds.In the first stages of theevo’ution of thistheory, octets were considered as necessarily cubical for, offhand, the cube appeared to be the form that must be the most stable one for 8 mutually-repelling electrons. This cubical octet, as a first approximation, was ofgreat value, for itplainly indicated two different types of combination: the shared pair of electrons or non-polar “bond,” and the electrostatic attraction betweencomplete, charged octets, or octets and hydrogen kernels, which we recognize as ionic combination. It also made clear that “pentavalent” nitrogen does not have 5 organic-type bonds. No contributions of value, beyond those of the old valence theory, were recognizedat the time as affecting carbon, hydrogenandoxygen as they exist in organic compounds. More-over, the cubical form of carbon was not compatible withoptical activity, which demanded atoms essentially tetrahedral. As Lewis has recently stated, 4 his first paperhad not yet been published before he had decided that the octet was perhaps more likely tetrahedral than cubical. This tetrahedral type, however, demanded that electrons exist more or less in pairs, an arrangement apparently not consistent with their being electrically charged. The magneton theory of Parson, 5 wherein he considered electrons as unit magnetic systems as well as units of negative