Crystal structures of three β-halolactic acids: hydrogen bonding resulting in differing Z′

Abstract

The crystal structures of three β-halolactic acids have been determined, namely, β-chlorolactic acid (systematic name: 3-chloro-2-hydroxypropanoic acid, C3H5ClO3) (I), β-bromolactic acid (systematic name: 3-bromo-2-hydroxypropanoic acid, C3H5BrO3) (II), and β-iodolactic acid (systematic name: 2-hydroxy-3-iodopropanoic acid, C3H5IO3) (III). The number of molecules in the asymmetric unit of each crystal structure (Z′) was found to be two for I and II, and one for III, making I and II isostructural and III unique. The difference between the molecules in the asymmetric units of I and II is due to the direction of the hydrogen bond of the alcohol group to a neighboring molecule. Molecular packing shows that each structure has alternating layers of intermolecular hydrogen bonding and halogen–halogen interactions. Hirshfeld surfaces and two-dimensional fingerprint plots were analyzed to further explore the intermolecular interactions of these structures. In I and II, energy minimization is achieved by lowering of the symmetry to adopt two independent molecular conformations in the asymmetric unit.

Intermolecular Hydrogen Bonding in Alpha-Hydroxy Carboxylic Acids Crystals: Connectivity, Synthons, Supramolecular Motifs

“…We added our own data for compounds 1-6 to the same sample. In the current year, a publication [33] that contains data on the crystal structure of chloro-, bromo-, and iodolactic acids 6-8 appeared. The structures of all compounds whose supramolecular organization was studied in this work are shown in Scheme 6.…”

Single-Source Precursors for the Controlled Aqueous Synthesis of Bismuth Oxyhalides

“…The synthesis of 3chlorolactic acid has been fully described in our previous publication. 44 Briefly, (±)-3-chloropropane-1,2-diol was placed in a round-bottom flask. Concentrated nitric acid was added with stirring.…”

“…Fourier-transform infrared spectroscopy (FTIR), 1 H nuclear magnetic resonance spectroscopy (NMR), highresolution mass spectrometry (HRMS), and melting point match previous results (Figure S1). 44 Synthesis of Ethyl 3-Bromolactate. The synthesis of ethyl 3bromolactate is adapted from a literature procedure.…”