Publication detail

A H-1, C-13 and N-15 NMR spectroscopic and GIAO DFT study of ethyl 5-oxo-2-phenyl-4-(phenylhydrazono)-4,5-dihydro-1H-pyrrole-3-carboxylate

Authors: Lyčka Antonín | Luňák Stanislav | Aysha Tarek | Holuša Radim | Hrdina Radim

Year: 2010

Type of publication: článek v odborném periodiku

Name of source: Tetrahedron Letters

Publisher name: Pergamon-Elsevier Science Ltd.

Place: Oxford

Page from-to: 3149-3151

Titles:

Language	Name	Abstract	Keywords
cze	1H, 13C a 15N NMR spektroskopie a GIAO DFT studie ethyl 5-oxo-2-fenyl-4-(fenylhydrazono)-4,5-dihydro-1H-pyrrol-3-karboxylátu	15N-značený ethyl 5-oxo-2-fenyl-4-(2-fenylhydrazono)-4,5-dihydro-1H-pyrrol-3-karboxylát byl připraven azo-kopulací diazotovaného aniline (s použitím Na15NO2, 99% 15N) s ethyl 4,5-dihydro-5oxo-2-fenyl-(1H)-pyrrol-3-karboxylátu. Produkt tvořila směs s tautomerní hydrazono formou, což bylo potvrzeno 13C a 15N chemickými posuny a bylo pozorováno jako směs E a Z isomer v souladu s nJ(15N, 13C). Porovnání 1H NMR dat s GIAO DFT výpočty umožnilo určení konfigurace karboxy esterové skupiny obou isomer,	Tautomerie; Izomerizace; NMR; GIAO
eng	A H-1, C-13 and N-15 NMR spectroscopic and GIAO DFT study of ethyl 5-oxo-2-phenyl-4-(phenylhydrazono)-4,5-dihydro-1H-pyrrole-3-carboxylate	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-5oxo-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.	Tautomerism; Isomerization; NMR; GIAO

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