Dynamic H NMR study of 4-methylphenoxyimidoyl azides: conformational or configurational isomerisation? |
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| Authors: | Ali Reza Modarresi-Alam Hossein Keykha Hossein A Dabbagh |
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| Institution: | a Department of Chemistry, Sistan and Baluchestan University, Zahedan 98135, Iran
b College of Chemistry, Isfahan University of Technology, Isfahan 84156, IR, Iran |
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| Abstract: | Dynamic 1H NMR (500 MHz) investigation of 4-methylphenoxyimidoyl azides (4-CH3-C6H4-O-CN-Y)-N3, Y=4-CH3-C6H4-SO2-, 4-Br-C6H4-SO2-, C6H5SO2-, CH3-SO2-, -CN in acetone-d6 at temperature range of 195-280 K is reported. The observed free energy barrier (almost 12 kcal mol−1) is attributed to conformational isomerisation about the N-S bond for Y=4-CH3-C6H4-SO2-, 4-Br-C6H4-SO2-, C6H5SO2-, CH3-SO2- and (almost 14 kcal mol−1) to configurational isomerisation (E/Z) about CN bond for Y=-CN. |
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| Keywords: | Dynamic 1H NMR Imidoyl azides Tetrazoles E/Z isomerisation Rotation about the N-S bond |
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