SYNTHESIS AND STRUCTURE OF PIPERIDINOXYPHOSPHONATE COMPLEXES WITH IONS OF BIVALENT METALS

Abstract

The synthesis of the complexes of dimethyl [1-(2-ethoxyethyl)-4-hydroxypiperidin-4-yl]phosphonate possessing the property of a plant growth stimulator, with transition metal ions (Co+2, Ni+2, Mn+2 and Cu+2) has been described. Based on the analysis of the IR spectra of the obtained complexes, the formation of N-Me+2 bond and the shift of absorption band of P = O has been revealed in comparison with the analog of the ligand. Modeling has carried out using the semi-empirical PM3 method. It has been shown that the formation of a complex in which a divalent metal ion forms coordination bonds with nitrogen and oxygen atoms of P=O is energetically most advantageous, while the piperidine ring has the “boat” conformation.

References

[1] Bulygin S.Ju., Demishev L.F., Doronin V.A., Zarishnjak A.S., Pashhenko Ja.V., Turovskij Ju.E, Fateev A.I., Jakovenko M.M. Mikrojelementy v sel'skom hozjajstve / Pod red. chl.-kor. UAAN, d. s.-h. nauk, prof. S. Ju. Bulygina. Dnіpropetrovs'k: «Sіch», 2007. 100 p.
[2] Jel'shenbrojh K. Metalloorganicheskaja himija. M.: BINOM. Laboratorija znanij, 2011. 746 p.
[3] Noffke A.L., Habtemariam A., Pizarro A.M., Sadler P.J. Designing organometallic compounds for catalysis and therapy // Chem.Commun. 2012. 48(4). P. 5219-5246. DOI: 10.1039/c2cc30678f
[4] Yuan Z., Shen X. Syntheses, crystal structures and antimicrobial activities of Cu(II), Ru(II), and Pt(II) compounds with an anthracene-containing tripodal ligand // RSC Advances. 2015. 5(14). 10521-10528. DOI: 10.1039/C4RA09168J
[5] Kukhar V.P., Hudson H.R. Aminophosphonic and Aminophosphinic Acids, Chemistry and Biological Activity // J. Wiley & Sons Ltd: New York, 2000. 634 p.
[6] Konoplev V.E. Prjamoe metallirovanie organicheskih soedinenij kompleksami perehodnyh metallov: Monografija. M., 2015. P. 63.
[7] Pred. pat. 5011 RK. MKI⁶S07F211/48, A61N 43/40. 1-(2-jetoksijetil)-4-(dimetoksifosforil)-4-gidroksipiperidin, obladajushhij stimulirujushhej rost rastenij aktivnost'ju / Ju V.K., Praliev K.D.; zajavl. 28.12.95; opubl. 15.08.97. Bjul. №3.
[8] Tarasevich B.N. IK-spektry osnovnyh klasssov organicheskih soedinenij: Spravochnye materialy: M.: MGU, 2012. 55 p.