Anga, S and Biswas, S and Kottalanka, R K and Mallik, Bhabani Shankar and Panda, Tarun K
(2014)
Structural and Mechanistic Insights of Substituted Perimidine - Experimental and Computational Studies.
Canadian Chemical Transactions, 2 (1).
pp. 72-82.
ISSN 2291-6458
Abstract
We report here
the synthesis of phenyl(2
-
phenyl
-
2,3
-
dihydro
-
1H
-
perimidin
-
2
-
yl)methanone (
2
)
by the condensation reaction between 1,8
-
diaminonaphthalene (
1
) and benzil in equimolar ratio at
ambient temperature. Further reaction of compound
2
with one equivalent of sodium borohydride at 0 ºC
resulted in quantitative conversion of
ketone to corresponding alcohol, namely, phenyl(2
-
phenyl
-
2,3
-
dihydro
-
1H
-
perimidin
-
2
-
yl)methanol (
3
). The solid
-
state structures of both the compounds were
established using single
-
crystal X
-
ray diffraction analysis. We probed,
using quantum mechanics, the
mechanism of formation of compound
2
through two of the most plausible routes and observed that it was
more plausible that the first route, energy
-
wise, would result in product
2
. We also calculated the
stabilization energy of intermolecular hydrogen bond
ing, which leads to the formation of a dimer, which
has already been observed in the solid
-
state structure of compound
3
.
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