A H, C and N NMR spectroscopic and GIAO DFT study of ethyl 5-oxo-2-phenyl-4-(2-phenylhydrazono)-4,5-dihydro-1<em>H</em>-pyrrole-3-carboxylate期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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A H, C and N NMR spectroscopic and GIAO DFT study of ethyl 5-oxo-2-phenyl-4-(2-phenylhydrazono)-4,5-dihydro-1H-pyrrole-3-carboxylate

Authors:	Antonín Ly?ka Stanislav Luňák Jr Radim Holuša

Institution:	^a Research Institute for Organic Syntheses (VUOS), Rybitví 296, CZ-533 54 Pardubice 20, Czech Republic ^b University of Hradec Králové, Faculty of Education, Rokitanského 62, CZ 500 03 Hradec Králové 3, Czech Republic ^c Faculty of Chemical Technology, University of Pardubice, Studentská 95, CZ-532 10 Pardubice, Czech Republic

Abstract:	¹⁵N-Labelled ethyl 5-oxo-2-phenyl-4-(2-phenylhydrazono)-4,5-dihydro-1H-pyrrole-3-carboxylate was synthesized by azo-coupling of diazotized aniline (using Na¹⁵NO₂ , 99% ¹⁵N) with ethyl 4,5-dihydro-5-oxo-2-phenyl-(1H)-pyrrole-3-carboxylate. The product was formed as a tautomeric hydrazone mixture as confirmed by ¹³C and ¹⁵N chemical shifts, and was obtained as a mixture of E and Z isomers according to ⁿJ(¹⁵N, ¹³C). A comparison of the ¹H NMR data with GIAO DFT calculations enabled determination of the configuration of the carboxy ester group in both isomers.

Keywords:	Tautomerism Isomerization NMR GIAO
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