M. Cyrański, I. Wawer, A. Zielińska
Jun 1, 2001
Citations
0
Influential Citations
2
Citations
Journal
Journal of Physical Organic Chemistry
Abstract
The crystal structure of 1-(2-hydroxy-4-bromophenyl)-3-methyl-4-methyl-4-imidazolin-2-one was determined by x-ray diffraction. The structure is stabilized by intermolecular hydrogen bonds formed between the 2-hydroxy and central groups. Molecular modelling including ab initio calculations at the HF/6–31+G** level revealed that in the gas phase the molecule is stabilized by an intramolecular hydrogen bond. The derivatives with 3-alkyl, benzyl and phenyl substituents were studied by 13C NMR including solid-state 13C CP/MAS NMR [for 1-(2-hydroxy-4-bromophenyl)-3-methyl-4-methyl-4-imidazolin-2-one] and FT-IR methods. The differences in chemical shifts Δ = δliquid − δsolid are significant for aromatic carbons C(3) (−2.9 ppm), C(4) (3.6 ppm) and C(5) (−3.9 ppm) and, on the other side of the imidazoline ring, of C(7) (−1.5 ppm). These carbons are adjacent to N(1)—C(4), and are subject to the largest changes of the environment during reorientation of the imidazolin-2-one moiety. Copyright © 2001 John Wiley & Sons, Ltd.