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Updated: Jun 1, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
5-Meth-oxy-2-[(2-morpholinoeth-yl)-iminio-meth-yl]phenolate
Nooraziah Mohd Lair1, Hapipah Mohd Ali, Seik Weng Ng
1Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
Summary
The study found that the title compound, C(14)H(20)N(2)O(3), exists as zwitterions. These molecules form both intra-molecular and inter-molecular hydrogen bonds, leading to inversion dimers.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Zwitterionic compounds play crucial roles in biological systems.
- Understanding hydrogen bonding is key to predicting molecular interactions and properties.
Purpose of the Study:
- To elucidate the molecular structure and hydrogen bonding characteristics of the title compound, C(14)H(20)N(2)O(3).
- To investigate the formation of zwitterions and dimers in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of hydrogen bonding networks, including intra- and inter-molecular interactions.
Main Results:
- The title compound crystallizes with two independent molecules per asymmetric unit, both adopting a zwitterionic form.
- Protonation of imino nitrogen atoms was observed.
- Intra-molecular hydrogen bonds were formed between the =N-H unit and a negatively charged oxygen atom.
- Weaker inter-molecular N-H⋯O hydrogen bonds were identified, leading to the formation of inversion dimers.
Conclusions:
- The compound exists in a zwitterionic state in the crystal lattice.
- The identified hydrogen bonding patterns dictate the self-assembly of molecules into inversion dimers.
- This structural information is vital for understanding the compound's physical and chemical properties.
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