Aromatic Stabilization Energy and Magnetic Properties in Fulvalenes: Is There a Connection Between These Two Aromaticity Indices?

详细信息    查看全文

• 作者：Amnon Stanger
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：78
• 期：24
• 页码：12374-12380
• 全文大小：305K
• 年卷期：v.78,no.24(December 20, 2013)
• ISSN：1520-6904

文摘

The nucleus-independent chemical shift (NICS) and Coulombic energy of 15 j,k-fulvalenes (j, k = 3, 5, 7, 9, 11) were investigated. It was found that in all of the hetero derivatives (j 鈮?k) charge transfer between the rings occurs. It occurs when the one ring contains 4n + 1 and the other 4n + 3 蟺 electrons, forming two rings containing numbers of 蟺 electrons closer to 4n + 2, and also when both rings contain either 4n + 3 or 4n + 1 蟺 electrons, forming a partially aromatized ring and a partially antiaromatized ring. Both types of charge transfer are associated with aromatic stabilization energy. The NICS values are consistent with the above-described partial aromatization and antiaromatization. A semiquantitative relationship between the aromatic stabilization energy and NICS is given.