R. Patil, Dattatray Chadar, D. Chaudhari
Oct 5, 2014
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Influential Citations
21
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Journal
Journal of Molecular Structure
Abstract
Abstract We would like to introduce seven analogues of 2-( n -alkylamino)-1,4-napthoquinone (where n -alkyl is methyl in LH-1, ethyl in LH-2, propyl in LH-3, butyl in LH-4, pentyl in LH-5, hexyl in LH-6 and heptyl in LH-7). All the said analogues have been successfully synthesized from 1,4-naphthoquinone and well characterised using different spectroscopic techniques. Furthermore, in order to understand the mechanistic aspects of formation of LH-1–LH-7 compounds we could propose the mechanism. The FT-IR spectroscopic analysis of LH-1–LH-7 compounds indicating that the presence of characteristic band of N H group at ∼3340 cm −1 . This band could assigned to existence of intramolecular hydrogen bonding interactions. The 13 C-NMR spectroscopic technique has been used to study structural feature of LH-1–LH-7 compounds via HSQC, COSY and DEPT experiments. Finally, the structural aspects of the LH-2–LH-6 compounds have been confirmed by single crystal X-ray diffraction studies. We could observed that LH-2 compound crystallises in monoclinic space group P 2 1 / c , whereas LH-6 crystallises in triclinic P-1 space group. The molecule of LH-2 and LH-6 compounds forms dimers via N H⋯O hydrogen bonding interaction while polymeric chains of dimers have been seen via C H⋯O hydrogen bonding. It is very interesting to note that the molecules of LH-6 possessing a π – π stacking interaction between C⋯N of the neighbouring chains.