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CRYSTAL STRUCTURE, SPECTRAL CHARACTERISATION AND THERMAL STUDY OF A NOVEL COMPOUND (Z)-3-((2-HYDROXYPROPYL) AMINO)-N,N-DIMETHYLBUT-2-ENAMIDE

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Abstract

A novel organic compound namely, (Z)-3-((2-hydroxypropyl)amino)-N,N-dimethylbut-2-enamide was synthesised by reacting N,N′-dimethylacetoacetamide (DMACAC) and 1-amino-2-propanol. The crystal structure of this compound was determined using single crystal X-ray diffraction method which revealed a planar geometry. Stabilisation of this compound by intramolecular hydrogen bonding is discussed. It was further characterised by TG-DTA, FTIR, NMR and Mass spectrometry. The compound was found to undergo a single step weight loss giving 1.7% residue at 320 °C in a high pure N2 atmosphere and melts in the temperature range of 119-122 °C.

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REFERENCES

  1. R. W. Layer. The chemistry of imines. Chem. Rev., 1963, 63(5), 489-510. https://doi.org/10.1021/cr60225a003

    Article  CAS  Google Scholar 

  2. H. Tanak, M. Yavuz, and O. Büyükgüngör. 2-Methyl-6-[2-(trifluoromethyl)phenyliminomethyl]phenol. Acta Crystallogr., Sect. E: Struct. Rep. Online, 2009, 65(11), o2949. https://doi.org/10.1107/s1600536809044560

    Article  CAS  Google Scholar 

  3. H. Tanak, F. Toğurman, S. Kalecik, N. Dege, and M. Yavuz. 2-{(E)-[(2-methyl-3-nitrophenyl)imino]methyl}-4-nitrophenol. Acta Crystallogr., Sect. E: Struct. Rep. Online, 2013, 69(7), o1085. https://doi.org/10.1107/s1600536813015407

    Article  CAS  Google Scholar 

  4. A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, and T. Lectka. The development of the first catalyzed reaction of ketenes and imines: catalytic, asymmetric synthesis of β-lactams. J. Am. Chem. Soc., 2002, 124(23), 6626-6635. https://doi.org/10.1021/ja0258226

    Article  CAS  PubMed  Google Scholar 

  5. M. D. Cohen, G. M. J. Schmidt, and S. Flavian. 388. Topochemistry. Part VI. Experiments on photochromy and thermochromy of crystalline anils of salicylaldehydes. J. Chem. Soc., 1964, 2041. https://doi.org/10.1039/jr9640002041

    Article  Google Scholar 

  6. E. Hadjoudis, M. Vittorakis, and I. Moustakali-Mavridis. Photochromism and thermochromism of Schiff bases in the solid state and in rigid glasses. Tetrahedron, 1987, 43(7), 1345-1360. https://doi.org/10.1016/s0040-4020(01)90255-8

    Article  CAS  Google Scholar 

  7. H. Tanak, Y. Bingöl Alpaslan, M. Yavuz, E. Ağar, F. Erşahin, and O. Büyükgüngör. 2-[(2,4-Dimethylphenyl)iminomethyl]-3,5-dimethoxyphenol. Acta Crystallogr., Sect. E: Struct. Rep. Online, 2009, 65(7), o1572. https://doi.org/10.1107/s1600536809021278

    Article  CAS  Google Scholar 

  8. E. Sinn and C. M. Harris. Schiff base metal complexes as ligands. Coord. Chem. Rev., 1969, 4(4), 391-422. https://doi.org/10.1016/s0010-8545(00)80080-6

    Article  CAS  Google Scholar 

  9. S. A. Kuby. A Study of Enzymes. Boca Raton, FL, USA: CRC Press, 1990, Vol. 2.

  10. H. Nozaki, H. Takaya, S. Moriuti, and R. Noyori. Homogeneous catalysis in the decomposition of diazo compounds by copper chelates. Tetrahedron, 1968, 24(9), 3655-3669. https://doi.org/10.1016/s0040-4020(01)91998-2

    Article  CAS  Google Scholar 

  11. S. Doherty, R. J. Errington, N. Housley, J. Ridland, W. Clegg, and M. R. J. Elsegood. N-Alkoxy-β-ketoiminate complexes of groups 4 and 5: synthesis and characterization of the complexes [(η5-C5H4R)M{CH3C(O)CHC(NCH2CHR′O)CH3}Cln] (M = Ti, n = 1; M = Nb, n = 2; R = H, Me; R′ = H, Me), [Ti{CH3C(O)CHC(NCH2CHR′O)CH3}Cl2(thf)], and [Ti{CH3C(O)CHC(NCH2CHR′O)CH3}2]. Organometallics, 1999, 18(6), 1018-1029. https://doi.org/10.1021/om980510q

    Article  CAS  Google Scholar 

  12. S. Arockiasamy, V. S. Raghunathan, P. A. Premkumar, P. Kuppusami, A. Dasgupta, P. Parameswaran, C. Mallika, and K. S. Nagaraja. Plasma-assisted MOCVD of titanium oxide and its composite coatings using metallo-organic precursors. Chem. Vap. Deposition, 2007, 13(12), 691-697. https://doi.org/10.1002/cvde.200706627

    Article  CAS  Google Scholar 

  13. N. Dege. Synthesis, crystal structure, Hirshfeld surface analysis of bis(N,N-diethylenediamine)cadmium(II)] dichloride. J. Struct. Chem., 2023, 64(4), 563-570. https://doi.org/10.1134/s0022476623040042

    Article  CAS  Google Scholar 

  14. S. Hamamci Alisir, N. Dege, and R. Tapramaz. Synthesis, crystal structures and characterizations of three new copper(II) complexes including anti-inflammatory diclofenac. Acta Crystallogr., Sect. C: Struct. Chem., 2019, 75(4), 388-397. https://doi.org/10.1107/s2053229619001827

    Article  CAS  Google Scholar 

  15. G. M. Sheldrick. SHELXL, version 2014. Göttingen, Germany: University of Göttingen, 2014.

  16. I. Moustakali-Mavridis, E. Hadjoudis, and A. Mavridis. Crystal and molecular structure of some thermochromic Schiff bases. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1978, 34(12), 3709-3715. https://doi.org/10.1107/s0567740878011930

    Article  Google Scholar 

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Correspondence to S. Arockiasamy.

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Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 9, 116731.https://doi.org/10.26902/JSC_id116731

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Sindhu, S., Arockiasamy, S. CRYSTAL STRUCTURE, SPECTRAL CHARACTERISATION AND THERMAL STUDY OF A NOVEL COMPOUND (Z)-3-((2-HYDROXYPROPYL) AMINO)-N,N-DIMETHYLBUT-2-ENAMIDE. J Struct Chem 64, 1677–1685 (2023). https://doi.org/10.1134/S0022476623090111

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