Differential Behavior of Amino-Imino Constitutional Isomers in Nonlinear Optical Processes

作者：Latorre Sonia; Moreira Iberio de P R; Villacampa Belen; Julia Lluis; Velasco Dolores; Maria Bofill Josep; Lopez Calahorra Francisco

来源：ChemPhysChem, 2010, 11(4): 912-919.

DOI：10.1002/cphc.200900616

• ab initio calculations
• heterocyclic compounds
• nonlinear optics
• tautomerism
• valence-bond model

A detailed study of the "blocked" amino-imino tautomers derived from N-acridine-substituted 2-aminobenzothiazole-and their effect on the nonlinear optical response-is presented. The synthesis, characterization, and nonlinear optical properties of these frozen tautomers namely N-methyl-N-(2-nitroacridin-3-yl)-2-aminobenzothia-zole and 3-methyl-N-(7-nitroacridin-3-yl)-2-iminobenzothiazole, are reported. A theoretical model based on valence-bond theory is also proposed and used to analyze the effect of the nuclear configuration corresponding to each frozen tautomer structure. In the present case the aromatic form and the allylic-anion-like system of the -N-C-N- group inherent to each isomer are crucial for understanding and analyzing the different response of each blocked tautomer.

• 出版日期2010-3-5