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Updated: Jun 1, 2026
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05:15
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Cyclo-hexane-1-spiro-2'-imidazolidine-5'-spiro-1''-cyclo-hexan-4'-one
Summary
This study details the molecular structure of a novel organic compound, C(13)H(22)N(2)O. The research reveals specific ring conformations and intermolecular hydrogen bonding in its crystal form.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Imidazolidine and cyclohexane derivatives are common scaffolds in medicinal chemistry and materials science.
Purpose of the Study:
- To elucidate the precise molecular geometry and crystal packing of the title compound, C(13)H(22)N(2)O.
- To investigate the intermolecular interactions governing the solid-state structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Analysis of bond lengths, bond angles, and non-covalent interactions was performed.
Main Results:
- The central imidazolidine ring adopts an envelope conformation.
- The two fused cyclohexane rings exhibit chair conformations.
- Molecules form centrosymmetric dimers through N-H⋯O hydrogen bonds, a common motif in crystal engineering.
Conclusions:
- The study provides a detailed structural characterization of C(13)H(22)N(2)O.
- The identified hydrogen bonding pattern highlights the role of intermolecular forces in stabilizing the crystal lattice.
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The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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For example, in...
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For example, in...
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Removing one hydrogen from the intervening CH2 group with both...
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