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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

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...
Stereoisomerism of Cyclic Compounds02:33

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,...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

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.
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

r-2,c-6-Bis(4-methoxy-phen-yl)-c-3,t-3-dimethyl-piperidin-4-one.

S Ponnuswamy, V Mohanraj, P Gayathri

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of C(21)H(25)NO(3), revealing two independent molecules with piperidine rings in a chair conformation. Both molecules exhibit equatorial methoxy-phenyl rings and are connected by hydrogen bonds and C-H⋯π interactions.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • The specific conformation and intermolecular interactions of compounds like C(21)H(25)NO(3) influence their solid-state behavior and potential applications.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(21)H(25)NO(3).
    • To analyze the molecular conformation, including the piperidine ring and methoxy-phenyl substituents.
    • To identify and describe the intermolecular interactions present in the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
    • Identification of hydrogen bonds (N-H⋯O) and C-H⋯π interactions characterized the crystal packing.

    Main Results:

    • The asymmetric unit contains two crystallographically independent molecules (A and B).
    • In both molecules, the piperidine ring adopts a chair conformation with equatorially attached methoxy-phenyl rings.
    • Dihedral angles between benzene rings were measured as 73.79°(8) for molecule A and 77.71°(8) for molecule B.
    • Intermolecular N-H⋯O hydrogen bonds and C-H⋯π interactions were identified, linking the molecules in the crystal structure.

    Conclusions:

    • The crystal structure of C(21)H(25)NO(3) has been successfully determined.
    • The conformational preferences and intermolecular interactions provide a detailed understanding of the compound's solid-state organization.
    • This structural information is fundamental for further studies on the compound's physical and chemical properties.