Further studies on the rotational barriers of Carbamates. An NMR and DFT analysis of the solvent effect for Cyclohexyl N,N-dimethylcarbamate

N‐arylamides and N‐arylcarbamates NCO internal rotation barrier study by molecular modeling

“…Carbamates, despite their many biological activities and structural similarity to amides, have been far less studied [10,16,17,[28][29][30][31][32][33][34]. Ab initio calculations (HF/3-21G(*)) by Souza and coworkers [31] on methyl N,N-dimethylcarbamate provided a totally planar Z-rotamer, similar to its X-ray crystallographic structure.…”

A simple and efficient synthesis and dynamic NMR studies of some new podands of dithiocarbamates formed from bis(naphthyl) derivatives

“…Delocalization of the nitrogen lone pair over the NCS π system leads the CN bond to acquire a double‐bond character, making the rotational barrier substantially higher than that is observed for simple amines 21–25. The CN rotational barrier in dithiocarbamates lies in the vicinity of 10–15 kcal mol –1 26,27 and carbamates in the vicinity of 15 kcal mol –1 , whereas in amides the values range from 15 to 22 kcal mol –1 21,28–37. Amides were extensively studied, and much is known about the origin of the CN rotational barrier and the influence of the medium.…”

Synthesis and Dynamic NMR Studies of Some New Symmetrical Podands of Dithiocarbamates Formed from Bis(N‐thiazol)chloroacetamides

“…Delocalization of the nitrogen lone pair over the N―C―S π system, leads the C―N bond to acquire double‐bond character making the rotational barrier substantially higher than simple amines . The C―N rotational barrier in DTCs lies on the vicinity of 10–15 kcal/mol 26, and carbamates equals to 15 kcal/mol while in amides the values are ranged from 15 to 22 kcal/mol . Amides were extensively studied and much is known about the origin of the C―N rotational barrier and on the influence of the medium.…”