Molecular structure of N-(2-phenylethyl)amide of α-(1,1-ethylenedioxy)-ethyl γ-hydroxybutyric acid (I) and¹H NMR spectra of (I) and N-(p-methoxybenzyl)derivative (III)

Abstract

The spectroscopic and X-ray investigation of the N-(2-phenylethyl) amide of α-(1,1-ethylenedioxy)-ethyl-γ-hydroxybutyric acid are reported. The¹H NMR spectra for the title structure and for the N-(p-methoxybenzyl) amide of α-(1,1-ethylenedioxy)-ethyl-γ-hydroxybutyric acid are given. The N-(2-phenylethyl)amide of α-(1,1-ethylenedioxy)-ethyl-γ-hydroxybutyric acid, C₁₆H₂₃O₄N, crustallizes in the monoclinic space groupP2 ₁/c witha=21.547(5),b=6.333(2),c=11.822(3) Å and β=101.01(2)°. The dioxolane ring has a half-chair conformation with ΔC₂(O3)=2.4° and |φ|_av=18.2°. The inconsiderable deviations from planarity of the six atoms of the amide group are caused mainly by twist around the C4−N1 bond and out-of-plane bending at the N1 atom (τ(C4−N1)=4°, X_N =7°, X_c =0.4° ). The amide group plane is nearly coplanar with the phenyl ring. The molecules are connected by two intermolecular hydrogen bonds.