Struct. Chem. 16, 339-345 (2005)

DOI: 10.1007/s11224-005-4464-7

Dimers of 1,8a-dihydro-1,8-naphthyridine derivatives as models of chiral self-recognition

A theoretical study of the dimer formation of chiral 1,8a-dihydro-1,8-naphthyridine derivatives has been carried out by means of DFT calculations. In the cases treated, the heterochiral dimers (RS orSR) are always more stable than the homochiral ones (RR or SS). Two possible proton transfer processes have been studied, the concerted and the non-concerted ones. The non-concerted TS corresponds to a true TS while the concerted one presents two imaginary frequencies. The geometrical characteristics of the hydrogen bonds in all the structures calculated have been correlated using the Steiner–Limbach model.