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11:45
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Piperidine-1-carboximidamide.
1Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany.
Acta Crystallographica. Section E, Structure Reports Online
|January 4, 2013
Summary
This study details the molecular structure of a nitrogen-rich compound, C(6)H(13)N(3). Analysis reveals specific bond lengths and angles within the CN(3) unit and a piperidine ring, with molecules forming a 2D network via hydrogen bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the structural properties of nitrogen-rich organic compounds is crucial for developing new materials.
- The specific compound C(6)H(13)N(3) presents an interesting case for structural analysis due to its CN(3) unit and piperidine ring.
Purpose of the Study:
- To elucidate the detailed molecular and crystal structure of the compound C(6)H(13)N(3).
- To analyze the bonding characteristics within the CN(3) functional group and the conformation of the piperidine ring.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonding) was performed.
Main Results:
- The CN(3) unit exhibits both double- and single-bond character, with specific bond lengths of 1.3090(17) Å (C=N) and 1.3640(17) Å (C-NH(2)) and 1.3773(16) Å.
- The N-C-N angles deviate from ideal trigonal-planar geometry, measuring 116.82(12)°, 119.08(11)°, and 124.09(11)°.
- The piperidine ring adopts a chair conformation, and molecules are organized into a two-dimensional network through N-H⋯N hydrogen bonds in the crystal.
Conclusions:
- The structural analysis provides a comprehensive understanding of the bonding and conformational preferences in C(6)H(13)N(3).
- The observed hydrogen bonding network highlights the potential for supramolecular assembly and material design based on this compound.
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The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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