Skorupska, Ewa A. published the artcileDynamic 1H NMR spectroscopic study of hindered internal rotation in selected N,N-dialkyl isonicotinamides: an experimental and DFT analysis, Formula: C10H14N2O, the publication is Tetrahedron (2013), 69(38), 8147-8154, database is CAplus.
Dynamic 1H NMR measurements were performed for N,N-dialkyl isonicotinamides (alkyl = Me, Et, and Me2CH). Two complementary methods of the anal. of these spectra were used, targeting the estimation of rates of alkyl group exchange and thereby parameters for rotation around the C-N bond. The Gibbs free activation energy in DMSO, ΔGexp≠, is 67.6, 65.3, and 61.4 kJ mol-1, resp. This finding was compared with related DFT and MP2 results on simulated solutions, ΔGcalcd≠s, in search of the best theor. tool reflecting the observed trend that ΔGexp≠ reduces with an increasing bulkiness of the N-alkyl group. Especially, the DFT methods recommended for TS geometry and barrier height calculations were used. The barriers to Car-C(O) bond rotation were also computed, although not measured exptl. An IRC anal. was also carried out. As a result, the above trend was rationalized by steric hindrance in the ground-state forms under study. The changes in their geometric parameters, including pyramidicity descriptors, are fully consistent with such explanation. Among all DFT methods tested, only the use of the BB1K/6-31+G(d,p)/IEF-PCM(DMSO) protocol afforded ΔGcalcd≠s fully comparable to the present DNMR determinations
Tetrahedron published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C12H14BNO2, Formula: C10H14N2O.
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