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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...
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.
Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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Green Synthesis of Quinoline-Based Ionic Liquid
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1-(6,8-Dibromo-2-methyl-quinolin-3-yl)ethanone.

R Prasath, P Bhavana, Seik Weng Ng

    Acta Crystallographica. Section E, Structure Reports Online
    |November 8, 2011
    PubMed
    Summary

    This study details the crystal structure of C(12)H(9)Br(2)NO, revealing two similar molecules in the asymmetric unit. Differences in ketone-methyl group orientation and crystal packing stabilized by hydrogen bonds and pi-pi interactions were observed.

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    Published on: February 15, 2016

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Solid-State Chemistry

    Background:

    • The asymmetric unit of a crystal structure can contain multiple independent molecules.
    • Intermolecular interactions, such as hydrogen bonds and pi-pi stacking, play a crucial role in crystal packing.
    • Conformational analysis is essential for understanding molecular behavior in the solid state.

    Purpose of the Study:

    • To determine and analyze the crystal structure of the compound C(12)H(9)Br(2)NO.
    • To investigate the conformational differences between independent molecules within the asymmetric unit.
    • To elucidate the intermolecular interactions governing the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and torsion angles to describe molecular conformation.
    • Identification and quantification of intermolecular interactions, including C-H···O, C-H···Br, and pi-pi interactions.

    Main Results:

    • The asymmetric unit contains two independent molecules (1 and 2) with similar conformations.
    • A notable difference was observed in the relative orientation of the ketone-methyl groups, indicated by distinct C-C-C-C torsion angles (-1.7(6)° for molecule 1 and -16.8(6)° for molecule 2).
    • Crystal packing is characterized by layered structures stabilized by C-H···O and pi-pi interactions, with additional C-H···Br contacts.

    Conclusions:

    • The crystal structure of C(12)H(9)Br(2)NO reveals nuanced conformational variations between independent molecules.
    • The observed crystal packing is primarily driven by a combination of hydrogen bonding and pi-pi stacking interactions.
    • Understanding these structural features provides insights into the solid-state behavior of this compound.