کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1409551 | 1501792 | 2012 | 9 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Experimental and theoretical study on the reaction of N3-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride Experimental and theoretical study on the reaction of N3-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride](/preview/png/1409551.png)
Two new 1,2,4-triazole-containing alkenoic acid derivatives were obtained from the reaction of N-phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride, depending on the reaction conditions. The structures of 2-((4-phenyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl)methyl)acrylic acid or (E)-2-methyl-3(4-phenyl-5-(pyridine-2-yl)-4H-1,2,4-triazol-3-yl)acrylic acid were confirmed by means of 1D and 2D NMR spectroscopic data as well as by single-crystal X-ray diffraction analysis. The experiential 1H and 13C chemical shifts were compared with those calculated with B3LYP, EDF1, and EDF2 density functional theories. The theoretical study of the observed terminal-to-internal alkene isomerization was performed with density functional (DFT) B3LYP/6-31+G∗ method using SM8 water and DMF solvation models. Antimicrobial activities of the newly prepared alkenoic acid derivatives were verified experimentally by a broth microdilution method.
► New isomeric 1,2,4-triazole-containing alkenoic acids are obtained.
► Mechanisms of base-catalyzed and neutral thermal 1,3-proton shifts are studied theoretically.
► The structures are confirmed by 1D and 2D NMR and single crystal X-ray diffraction analysis.
► Antimicrobial activity of the 1,2,4-triazole-containing alkenoic acids are investigated.
Journal: Journal of Molecular Structure - Volume 1022, 29 August 2012, Pages 211–219