Ethyl 3-[1-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorin-2-yl)propan-2-ylidene]carbazate: a combined X-ray and density functional theory (DFT) study.
In the title compound, C(11)H(21)N(2)O(5)P, one of the two carbazate N atoms is involved in the C=N double bond and the H atom of the second N atom is engaged in an intramolecular hydrogen bond with an O atom from the dimethylphosphorin-2-yl group, which is in an uncommon cis position with respect to the carbamate group. The cohesion of the crystal structure is also reinforced by weak intermolecular hydrogen bonds. Density functional theory (DFT) calculations at the B3LYP/6-311++g(2d,2p) level revealed the lowest energy structure to have a Z configuration at the C=N bond, which is consistent with the configuration found in the X-ray crystal structure, as well as a less stable E counterpart which lies 2.0 kcal mol(-1) higher in potential energy. Correlations between the experimental and computational studies are discussed.
Arfaoui
Youssef
Y
Laboratoire de Chimie Physique, Faculté des Sciences, El Manar II, 2092 Tunis, Tunisia.
Kouass
Salah
S
Salah
Nesrine
N
Ben Akacha
Azaiez
A
Guesmi
Abderrahmen
A