Producción Científica Profesorado

Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study



Tlahuextl Romero, Angela Margarita

1998

F. J. Martínez-Martínez, I. I. Padilla-Martínez, M. A. Brito, E. D. Geniz, R. C. Rojas, J. B. R. Saavedra, H. Höpfl, Margarita Tlahuextl, R. Contreras, 12. Three-center intramolecular hidrogen bonding in oxamide derivatives. NMR and X-ray diffraction study, J. Chem. Soc. Perkin Trans. 2, 401-406 (1998). DOI: 10.1039/A704640E


Abstract


This contribution describes the synthesis and structural investigation of the symmetric and non-symmetric oxamides N,N?-bis(2-hydroxyphenyl)oxamide 1, N,N?-bis(5-tert-butyl-2-hydroxyphenyl)oxamide 2, N,N?-bis(3,5-dimethyl-2-hydroxyphenyl)oxamide 3, N,N?-bis(2-hydroxybenzyl)oxamide 4, N,N?-diphenethyloxamide 5, N-(2-hydroxyphenyl)-N?-(2-methoxyphenyl)oxamide 6, N-(2-hydroxyphenyl)-N?-phenethyloxamide 7, (1S,2R)-()-N-(2-hydroxyphenylcarbamoylcarbonyl)norephedrine 8, (1R,2S)-()-N-(2-hydroxyphenylcarbamoylcarbonyl) 9, ethyl N-(2-hydroxyphenyl)oxalamate 10 and ethyl N-(2-methoxyphenyl)oxalamate 11. The structures were established by 1H, 13C, 15N and variable temperature NMR spectroscopy. Compounds 14 and 611 are stabilized by intramolecular three-center hydrogen bonding between the amide proton and two oxygen atoms. The 1H NMR ??/?T value of the amide proton correlates with the 15N NMR chemical shift. The X-ray diffraction molecular structures of 1 and 11 showed a planar conformation with trans configuration in the solid state, corresponding to the preferred conformation found in solution.



Producto de Investigación




Artículos relacionados

SYNTHESIS OF NOVEL DINUCLEAR COMPLEXES OF Fe(O) DERIVED FROM 1,2-DICARBONYLIC MONOHYDRAZONES

Hydrogen bond studies in substituted N-(2-hydroxyphenyl)--2-[(4-methylbenzenesulfonyl)amino]acetamid...

Coordination chemistry of iminodiacetic esters. Structural and spectroscopic characterization of cop...

Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides

Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides

Synthesis and structural studies of N-(p-toluenesulfonyl)-amino acid 3,5-di-tert-butyl-2-phenolamide...

Diastereoselective alkylation of chiral glycinate derivatives containing the a-phenylethyl group.

Speciation of the new ligand di-isopropyliminodiacetoamide with Cu(II) using computational processin...

Synthesis of Zn compounds derived from 1H-benzimidazol-2-ylmethanamine

1 H, 13C, 15N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structur...