116668-54-3Relevant articles and documents
New models for the study of the racemization mechanism of carbodiimides. Synthesis and structure (X-ray crystallography and 1H NMR) of cyclic carbodiimides
Molina, Pedro,Alajarín, Mateo,Sánchez-Andrada, Pilar,Carrió, Juan Server,Martínez-Ripoll, Martín,Anderson, J. Edgar,Jimeno, María Luisa,Elguero, José
, p. 4289 - 4299 (2007/10/03)
The crystal and molecular structure of carbodiimides 2 (5,6,18,19-tetradehydro-5,12,13,18,25,26-hexahydrotetrabenzo[d,h,m,q][1,3,10,12] tetraazacyclooctadecine) and 3 (8,10,22,24-tetraazapentacyclo-[23.3.1.3,7.111,15.1 17,21]dotriaconta-1(29),3,5,7(32),8,9,11,13,15(31),17,19,21(30),22, 23,25,27-hexadecaene) have been determined. The activation barriers for the racemization of carbodiimides 1 (6,7-dihydrodibenzo[d,h][1,3]diazonine), 2, and 3 have been determined. While 1 presents a relatively high barrier (17.4 kcal mol-1), 2 and 3 have very low activation barriers (between 5 and 7 kcal mol-1). We tentatively conclude that open-chain and large-ring carbodiimides racemize by nitrogen inversion or trans-rotation while medium-size cyclic carbodiimides racemize by cis-rotation.