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Related Concept Videos

Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Opioid Analgesics: Morphine and Other Natural Cogeners

Opioids are a class of drugs that mimic endogenous opioid peptides and act on opioid receptors, and help in pain relief. These compounds are classified as natural, synthetic, or semi-synthetic. Natural opioids, like morphine, codeine, and thebaine, are derived from the opium poppy plant (Papaver somniferum or Papaver album) and are termed opiates. Synthetic opioids are artificial, while semi-synthetic opioids combine natural and synthetic compounds. Morphine, a prototypical opioid, possesses a...

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4-(4-Nitro-phen-yl)morpholine.

Li-Jiao Wang, Wei-Wei Li, Sheng-Yong Yang

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2012
    PubMed
    Summary
    This summary is machine-generated.

    Aromatic π-π stacking interactions were found to stabilize the crystal structure of C(10)H(12)N(2)O(3). The morpholine ring within this compound adopts a chair conformation, contributing to its structural stability.

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    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

    Published on: January 3, 2018

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding intermolecular forces is crucial for predicting and controlling material properties.
    • Aromatic π-π stacking is a key non-covalent interaction in organic solids.
    • Crystal structure analysis provides fundamental insights into molecular arrangement and stability.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(10)H(12)N(2)O(3).
    • To investigate the role of aromatic π-π stacking interactions in stabilizing the crystal lattice.
    • To determine the conformational preferences of the morpholine ring within the crystal structure.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
    • Analysis of intermolecular distances and angles was performed to identify and quantify specific interactions.
    • Conformational analysis of the morpholine ring was conducted based on the determined atomic coordinates.

    Main Results:

    • The crystal structure of C(10)H(12)N(2)O(3) was successfully determined.
    • Significant aromatic π-π stacking interactions were identified, with a perpendicular distance of 3.7721(8) Å between parallel planes, confirming their role in stabilization.
    • The morpholine ring was observed to adopt a chair conformation.

    Conclusions:

    • Aromatic π-π stacking interactions are a primary stabilizing force in the crystal structure of C(10)H(12)N(2)O(3).
    • The chair conformation of the morpholine ring is consistent with typical conformational preferences for such saturated heterocycles.
    • This study provides valuable data on the interplay of non-covalent interactions and molecular conformation in organic crystal engineering.