Physical Science International Journal

Synthesis and Molecular Structure of (E)-Methyl 3-(2-Hydroxyphenyl)-2-(Piperidine-1-Carbonyl) Acrylate Stabilized by Hydrogen Bonding and C-H…π Interactions

Imtiaz Khan *

Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan

Aliya Ibrar

Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan

Bhajan Lal

Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan

Ataf Ali Altaf

Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan

Jonathan M. White

Bio-21 Institute, School of Chemistry, University of Melbourne, Parkville-3052, Australia

*Author to whom correspondence should be addressed.

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Abstract

The crystal and molecular structure of (E)-methyl 3-(2-hydroxyphenyl)-2-(piperidine-1-carbonyl)acrylate, synthesized by one-pot three component reaction of salicylaldehyde, diethyl malonate and piperidine, has been reported. The title compound 4 crystallizes from a mixture of petroleum ether/ethyl acetate in the monoclinic space group P21/n with lattice parameters a = 8.0099(3) Å, b = 19.6227(7) Å, c = 9.6322(4) Å, β = 107.004(4)°, V = 1447.77(10) ų and Z = 4. The molecules of the target compound 4 form H-bonded dimers in the crystal lattice. These dimers are held together by C-H…π interactions, between the piperidine equatorial α-hydrogen and the aromatic ring and C-H…O interactions between the axial α-piperidine hydrogen and the hydroxyl oxygen.

 

Keywords: Acrylate, crystal structure, hydrogen bonding, π-interactions

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