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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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3-Ethyl-4-methyl-1H-pyrazol-2-ium-5-olate.

R S Rathore, T Narasimhamurthy, R Venkat Ragavan

Acta Crystallographica. Section E, Structure Reports Online

|November 18, 2011

Summary

This study details a zwitterionic pyrazole derivative, C(6)H(10)N(2)O. Its crystal structure features unique iminium-amine hydrogen bonding, forming undulating sheets parallel to the (100) plane.

Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Pyrazole derivatives are important in medicinal chemistry and materials science.
Understanding crystal packing interactions is crucial for predicting material properties.

Purpose of the Study:

To characterize the crystal structure of the zwitterionic pyrazole derivative C(6)H(10)N(2)O.
To elucidate the dominant intermolecular interactions governing its crystal packing.

Main Methods:

Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
Analysis of hydrogen bonding and non-covalent interactions was performed.

Main Results:

The compound C(6)H(10)N(2)O exists as a zwitterion.

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A prominent three-center iminium-amine N(+)-H⋯O(-)⋯H-N interaction was identified.

These interactions lead to the formation of undulating sheet-like structures oriented parallel to the (100) crystallographic plane.

Conclusions:

The crystal structure is dominated by a specific hydrogen bonding motif.
The observed packing arrangement influences the solid-state properties of this zwitterionic pyrazole derivative.