Smith, Bradley D’s team published research in Tetrahedron Letters in 2004-03-22 | 639520-70-0

Tetrahedron Letters published new progress about C-N bond. 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Formula: C12H16BrNO2.

Smith, Bradley D.; Goodenough-Lashua, DeeAnne M.; D’Souza, Carlisle J. E.; Norton, Kieran J.; Schmidt, Leslie M.; Tung, James C. published the artcile< Substituent effects on the barrier to carbamate C-N rotation>, Formula: C12H16BrNO2, the main research area is substituent effect barrier carbamate carbon nitrogen rotation.

Seven aryl-substituted t-Bu N-methyl-N-aryl carbamates were prepared, and in each case, the barrier to C-N bond rotation, ΔG‡, was determined in CDCl3 solution using variable temperature NMR. A linear free energy relationship is observed between ΔG‡ and the electronic stabilization effect of the substituent on the N-aryl ring. More specifically, electron donating groups increase ΔG‡, whereas withdrawing groups decrease ΔG‡. A plot against σ- was more linear (r2=0.96), than a plot against σ (r2 = 0.90) or σ+ (r2 = 0.88) and a value of ρ = 1.76 was obtained at 243 K. Thus, rotation about the carbamate C-N bond in weakly polar chloroform involves a decrease in pos. charge on the nitrogen.

Tetrahedron Letters published new progress about C-N bond. 639520-70-0 belongs to class bromides-buliding-blocks, and the molecular formula is C12H16BrNO2, Formula: C12H16BrNO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary