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Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

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.

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

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,...

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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5,5-Dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one

Quiroga¹, Insuasty, Abonia

¹Grupo de Investigacion de Compuestos Heterociclicos, Departamento de Quimica, Universidad de Valle, AA 25360, Cali, Colombia.

Acta Crystallographica. Section C, Crystal Structure Communications

|December 19, 2000

Summary

This summary is machine-generated.

This study reveals how C(12)H(17)N(3)O molecules form a 3D network through specific hydrogen bonds. These bonds, involving nitrogen-hydrogen and oxygen atoms, dictate the compound's structural arrangement.

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Area of Science:

Crystal Engineering
Supramolecular Chemistry
Materials Science

Background:

Understanding intermolecular forces is crucial for designing novel materials.
Hydrogen bonding plays a key role in the self-assembly of molecular structures.
The specific arrangement of molecules dictates macroscopic properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound C(12)H(17)N(3)O.
To identify and characterize the hydrogen bonding interactions present in the crystal lattice.
To understand how these interactions lead to the formation of a three-dimensional network.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of hydrogen bond distances and angles was performed.
The formation of the extended three-dimensional network was visualized and analyzed.

Main Results:

The crystal structure of C(12)H(17)N(3)O was successfully determined.
Two distinct N-H…O hydrogen bonds were identified, linking adjacent molecules.
These hydrogen bonds result in the formation of an intricate three-dimensional supramolecular network.
Specific N…O distances of 2.804(3) Å and 2.766(3) Å were observed, with a common acceptor oxygen atom.

Conclusions:

The title compound C(12)H(17)N(3)O self-assembles into a robust 3D network via directed hydrogen bonding.
The identified hydrogen bonding motif is a significant factor in the compound's solid-state structure.
This structural insight could inform the design of related compounds with tailored properties.