Kinetic stabilization of N,N-dimethyl-2-propyn-1-amine N-oxide by encapsulation.
Thermally and in nonprotic media N,N-dimethyl-2-propyn-1-amine N-oxide undergoes two consecutive sigmatropic rearrangements affording propenal. Two molecular containers capable of the quantitative inclusion/encapsulation of the N-oxide are described. The N-oxide becomes kinetically stabilized when included in the containers. The relationship between the observed kinetic stabilization of the N-oxide and the thermodynamic and kinetic stability of its inclusion complexes is explained and modeled.
Institute of Chemical Research of Catalonia (ICIQ), Avgda. Països Catalans 16, 43007 Tarragona, Spain, and Catalan Institution for Research and Advanced Studies (ICREA), Passeig Lluís Companys, 23, 08018 Barcelona, Spain.
Albano
A
Galán
Guzmán
G
Gil-Ramírez
Pablo
P
Ballester
D000480:Alkynes / Q000737:chemistry*; D007700:Kinetics; D008958:Models, Molecular; D010087:Oxides / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D013816:Thermodynamics
D000480:Alkynes; C587467:N,N-dimethyl-2-propyn-1-amine N-oxide; D010087:Oxides; D010293:Pargyline