Differential Behavior of Amino–Imino Constitutional Isomers in Nonlinear Optical Processes |
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| Authors: | Sonia Latorre Ibério de P R Moreira Dr Belén Villacampa Dr Lluís Julià Dr Dolores Velasco Dr Josep Maria Bofill Prof Dr Francisco López‐Calahorra Prof Dr |
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| Institution: | 1. Departament de Química Orgànica, Institut de Nanociències i Nanotecnologia (IN2UB), Universitat de Barcelona, Martí i Franquès, 1‐11, 08028 Barcelona (Spain), Fax: (+34)?93‐339‐78‐78;2. Departament de Química Física, Institut de Química, Teòrica i Computacional (IQTCUB), Universitat de Barcelona, Martí i Franquès, 1‐11, 08028 Barcelona (Spain);3. Departamento de Física de la Materia Condensada, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza‐CSIC, 50009 Zaragoza (Spain);4. Departament de Química Orgànica Biològica i Modelització Molecular, Institut de Química, Avan?ada de Catalunya—CSIC, Jordi Girona, 18‐26, 08034 Barcelona (Spain);5. Departament de Química Orgànica, Institut de Química, Teòrica i Computacional (IQTCUB), Universitat de Barcelona, Martí i Franquès, 1‐11, 08028 Barcelona (Spain), Fax: (+34)?93‐339‐78‐78 |
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| Abstract: | 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‐6‐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 effects 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 responses of each “blocked” tautomer. |
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| Keywords: | ab initio calculations heterocyclic compounds nonlinear optics tautomerism valence– bond model |
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