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DOI: 10.1039/A704640E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 401-406

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

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F. J. Martínez-Martínez, I. I. Padilla-Martínez, M. A. Brito, E. D. Geniz, R. C. Rojas, J. B. R. Saavedra, H. Höpfl, M. Tlahuextl and R. Contreras

Abstract

This contribution describes the synthesis and structural investigation of the symmetric and non-symmetric oxamides N,N[hair space]′-bis(2-hydroxyphenyl)oxamide 1, N,N[hair space]′-bis(5-tert-butyl-2-hydroxyphenyl)oxamide 2, N,N[hair space]′-bis(3,5-dimethyl-2-hydroxyphenyl)oxamide 3, N,N[hair space]′-bis(2-hydroxybenzyl)oxamide 4, N,N[hair space]′-diphenethyloxamide 5, N-(2-hydroxyphenyl)-N[hair space]′-(2-methoxyphenyl)oxamide 6, N-(2-hydroxyphenyl)-N[hair space]′-phenethyloxamide 7, (1S,2R)-(–)-N-(2-hydroxyphenylcarbamoylcarbonyl)norephedrine 8, (1R,2S[hair space])-(–)-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 1–4 and 6–11 are stabilized by intramolecular three-center hydrogen bonding between the amide proton and two oxygen atoms. The 1H NMR Δδ/ΔT 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.

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