ci0497354_si_001.pdf (81.39 kB)
Molecular Modeling of Anti-Bredt Compounds
journal contribution
posted on 2005-03-28, 00:00 authored by Igor NovakThe molecular structure and thermochemical stability of 40 bicyclic alkenes and imines containing between
five and eight heavy atoms has been investigated computationally by high-level G3/B3LYP method. The
same method was also used to study their building blocks: monocyclic alkenes and imines. The relative
stability of isomers, standard enthalpies of formation and strain energies are discussed and compared. Our
results suggest that molecular mechanics provides an unsatisfactory description of strain energies in bridgehead
alkenes. Some bridgehead alkene and imine species represent structures which are not local minima on the
potential energy surface and are hence unlikely to be isolated. Furthermore, some bicyclic alkenes and
imines have open-shell 1,2-diradical character.