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Related Concept Videos

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Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

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The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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IUPAC Nomenclature of Aldehydes01:16

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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

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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.
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Separation of the aromatic...

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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
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N-(2-Methyl-phen-yl)maleamic acid.

B Thimme Gowda, Miroslav Tokarčík, K Shakuntala

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the molecular conformation of a novel compound, revealing an intramolecular hydrogen bond influencing its structure. Crystal analysis shows molecules forming zigzag chains via intermolecular hydrogen bonds and linked sheets through pi-pi interactions.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Supramolecular Chemistry

    Background:

    • Understanding molecular conformation and intermolecular interactions is crucial in chemical and materials science.
    • Maleamic acid derivatives are important building blocks in organic synthesis and polymer chemistry.
    • Intramolecular hydrogen bonding can significantly influence molecular geometry and reactivity.

    Purpose of the Study:

    • To elucidate the detailed molecular structure and conformation of the title compound (C(11)H(11)NO(3)).
    • To investigate the role of intramolecular hydrogen bonding on the observed molecular geometry.
    • To characterize the crystal packing and intermolecular interactions within the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Conformational analysis of the amide and carboxylic acid groups was performed.
    • Analysis of hydrogen bonding networks and π-π interactions in the crystal lattice was conducted.

    Main Results:

    • The N-H bond is anti to the C=O bond in the amide segment, and syn to the ortho-methyl group.
    • An intramolecular O-H⋯O hydrogen bond was observed between the carboxyl O-H and the amide carbonyl oxygen.
    • The phenyl ring forms a dihedral angle of 12.7° with the maleamic acid unit.
    • Intermolecular N-H⋯O hydrogen bonds create zigzag chains, further organized into sheets by π-π interactions (3.425 Å).

    Conclusions:

    • The molecular conformation is significantly influenced by an intramolecular hydrogen bond, leading to a rare anti-positioning of the carboxyl C=O and O-H bonds.
    • The crystal structure is characterized by a network of intermolecular hydrogen bonds and π-π stacking interactions.
    • This structural insight provides a foundation for understanding the properties and potential applications of this class of compounds.