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Synthesis of Propiolamide and 1 H, 13 C and 15 N NMR Spectra of Formamide, Acetamide and Propiolamide
Author(s) -
Ferris Thomas D.,
Lee Peter T.,
Farrar Thomas C.
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199709)35:9<571::aid-omr140>3.0.co;2-k
Subject(s) - chemistry , acetamide , formamide , carbon 13 nmr , acetonitrile , chemical shift , coupling constant , proton nmr , yield (engineering) , nmr spectra database , analytical chemistry (journal) , spectral line , organic chemistry , thermodynamics , physics , astronomy , particle physics
A high‐yield synthesis and purification of propiolamide is described. The structure and purity of the compound were confirmed by 1 H, 13 C and 15 N NMR studies. Natural abundance 13 C and 15 N chemical shift measurements in 3.0 M acetonitrile solutions are reported along with 1 H– 1 H, 1 H– 15 N and 1 H– 13 C spin coupling constants. Polarization transfer techniques were used for the 15 N and 13 C measurements. The propiolamide NMR parameters were compared with those for 3.0 M solutions of formamide and acetamide in acetonitrile solution. Measurements at 298 and 278 K indicated that for all three compounds there is still significant rotation about the carbon–nitrogen bond at room temperature. © 1997 by John Wiley & Sons, Ltd.