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New Schiff bases derived from benzyl carbazate with alkyl and heteroaryl ketones

Isolation, structural characterization, thermal behavior and molecular docking studies

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Abstract

The condensation reaction of benzyl carbazate with the ketones, viz., dimethylketone, dipropylketone, cyclobutanone, cyclopentanone, cyclohexanone, cycloheptanone, 2-acetylpyridine, 3-acetylpyridine and 4-acetylpyridine, yielded the Schiff bases [benzyl 2-(propan-2-ylidene)hydrazinecarboxylate (1), benzyl 2-(heptan-4-ylidene)hydrazinecarboxylate (2), benzyl 2-(cyclobutanylidene)hydrazinecarboxylate (3), benzyl 2-(cyclopentnylidene)hydrazinecarboxylate (4), benzyl 2-(cyclohexanylidene)hydrazinecarboxylate (5), benzyl 2-(cycloheptanylidene)hydrazinecarboxylate (6), benzyl 2-(1-(pyridine-2-yl) ethylidene)hydrazinecarboxylate (7), benzyl 2-(1-(pyridine-3-yl) ethylidene)hydrazinecarboxylate (8) and benzyl 2-(1-(pyridine-4-yl) ethylidene)hydrazinecarboxylate (9)], respectively. These were all characterized by elemental analysis, FT-IR and NMR (1H and 13C) spectroscopic methods, and in addition, the structures of compounds 4, 8 and 9 have been confirmed by single-crystal X-ray diffraction studies, and their crystal structures are shown to be stabilized by hydrogen bonding. The thermal properties of all the Schiff bases have been studied in air and all of them underwent melting followed by endo- and exothermic decomposition processes to yield an ethanimine (CH3–CH=NH) intermediate which in turn decomposes exothermically to give gaseous products. In a nitrogen atmosphere, these compounds also show similar thermal behavior but with the absence of an intermediate. A docking study of compounds 2, 4 and 9 with human BChE provides useful structural information on their inhibition properties.

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Acknowledgements

P. Nithya acknowledges University Grant Commission (UGC-SAP), New Delhi, for the award of BSR—Senior Research Fellowship. We thank the University of Otago for the purchase of the diffractometer, and the Chemistry Department, University of Otago, for the support of the work of JS. Our sincere thanks go to the SIF, VIT University, Vellore, for providing access to their NMR spectral facilities. COE-AMGT, Amrita Vishwa Vidyapeetham University, Coimbatore, is gratefully acknowledged for permitting us to record the TG–DTA under a nitrogen atmosphere.

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  1. Department of Chemistry, Bharathiar University, Coimbatore, 641 046, Tamil Nadu, India

    Palanivelu Nithya, Sannasi Helena, Ramar Rajamanikandan & Subbiah Govindarajan

  2. Department of Chemistry, University of Otago, Dunedin, 9054, New Zealand

    Jim Simpson

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  1. Palanivelu Nithya
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Correspondence to Subbiah Govindarajan.

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10973_2017_6205_MOESM1_ESM.doc

Supplementary material 1 Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number CCDC- 1455910-1455912. Copies of the data can be obtained free of charge from the CCDC (12 Union Road, Cambridge CB2 1EZ, UK; Tel.: +44-1223-336408; Fax: +44-1223-336003; e-mail: deposit@ccdc.cam.ac.uk; Web site http://www.ccdc.cam.ac.UK) (DOC 2532 kb)

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Nithya, P., Simpson, J., Helena, S. et al. New Schiff bases derived from benzyl carbazate with alkyl and heteroaryl ketones. J Therm Anal Calorim 129, 1001–1019 (2017). https://doi.org/10.1007/s10973-017-6205-8

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