Hydrogen bonding in 3-azetidinol
1990; Elsevier BV; Volume: 220; Linguagem: Inglês
10.1016/0022-2860(90)80098-5
ISSN1872-8014
AutoresUffe Anthoni, Daniel H. Christensen, Carsten Christophersen, Michael Gajhede, Lars Henriksen, O. Faurskov Nielsen, Per Halfdan Nielsen,
Tópico(s)Surfactants and Colloidal Systems
ResumoInvestigations of the hydrogen bonding of 3-azetidinol in the solid state by X-ray spectroscopy have been extended to solutions in CCl4 and water. Ab initio calculations ranging from the STO-3G to the 6–31G** level indicate that in addition to the non-associated form (A) a conformer with intramolecular hydrogen-bonding OH ··N (B) might occur in the approximate ratio 2:1. IR and 1H NMR spectroscopic studies on CCl4 solutions give evidence in support of this prediction. The IR spectra at low temperatures (−5°C) disclose the presence of an intermolecular hydrogen- bonded chain-stacking form (C) which has a strong affinity to water. Raman spectra in the R (ν) representation of an aqueous solution of 3-azetidinol in the range −400 to 400 cm−1 support the presence of C. A structure for is proposed based upon the X-ray results, involving stacking of the azetidinol rings and strong intermolecular hydrogen bonding necessitating the incorporation of water molecules. The proposal is supported by the ab initio results.
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