For the computation of bond dissociation energies (BDE), all sites that
are likely to act as H donors were considered (Scheme 2). They
correspond to those already present in the rasagiline framework (sitesa , b , c and d ), and the new possibilities
arising from incorporating functional groups (-OH, -NH2,
-SH and -COOH) in sites R1 to R4. These
four groups were chosen because they can enhance the antioxidant
behaviour and modify the acid-base ratio. Two rasagiline analogs were
used to analyze the effects of the terminal alkyne group in
physicochemical parameters, toxicity, synthetic accessibility, and the
global reactivity indexes. They are:
N-(propanyl)-2,3-dihydroinden-1-amine (RI), which
present a terminal methyl group instead of the corresponding rasagiline
terminal alkyne; and 1-(R)-aminoindan (RII) that present
no alkyl chain. The derived comparisons could be interesting since no
rational studies comparing these molecules have been carried out.
Because of this structural modification, the e site in
RI was included, while d site in
RII was not considered, for BDE calculations.