Structural and Mechanistic Insights of Substituted Perimidine - Experimental and Computational Studies

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

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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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IITH Creators:
IITH CreatorsORCiD
Mallik, Bhabani Shankarhttp://orcid.org/0000-0001-9657-1497
Panda, Tarun Khttp://orcid.org/0000-0003-0975-0118
Item Type: Article
Uncontrolled Keywords: Perimidine ; Heterocyclic; Transition State; Density Functional Theory; X - Ray; Hydrogen Bonding
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 24 Oct 2016 10:07
Last Modified: 07 Sep 2017 10:56
URI: http://raiithold.iith.ac.in/id/eprint/2829
Publisher URL: https://doi.org/10.13179/canchemtrans.2014.02.01.0...
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