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Updated: May 26, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
A DFT study of the interaction between microhydrated anions and naphthalendiimides
Alba Campo-Cacharrón1, Enrique M Cabaleiro-Lago, Jesús Rodríguez-Otero
1Departamento de Química Física, Facultade de Ciencias, Universidade de Santiago de Compostela, Lugo, Galicia, Spain.
Abstract:
The characteristics of the interaction of anions with naphthalendiimides, the basic structural motif of a newly synthesized anion channel based on anion···π interactions, are studied by computational methods. Stable complexes are formed with bromide, chloride, fluoride or hydroxide anions, which exhibit strong anion···π interactions in the gas phase. Following the sequence of the polarizing power of the anions, hydroxide and fluoride complexes are the most strongly interacting. The presence of a small number of water molecules strongly affects the anion···π interactions, especially for hydroxide and fluoride complexes, so the differences in interaction strength among the anions drop significantly. The calculations suggest that a small number of water molecules can be crucial to reducing dehydration cost and contributing to stabilizing interactions with the naphthalendiimide units.
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