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Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
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When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
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Structure of Amines01:19

Structure of Amines

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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
2.8K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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Structures of Carboxylic Acid Derivatives01:28

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.9K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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The crystal structures of three disordered 2-substituted benzimidazole esters.

Chayanna Harish Chinthal1, Hemmige S Yathirajan1, Nagaraja Manju2

  • 1Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.

Acta Crystallographica. Section E, Crystallographic Communications
|May 24, 2021
PubMed
Summary

Three benzimidazole ester crystal structures reveal molecular disorder, impacting aggregation. This study details the specific disorder in substituents and their effects on intermolecular interactions and crystal packing.

Keywords:
benzimidazolescrystal structuredisorderheterocyclic compoundshydrogen bondingsupra­molecular assembly

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Area of Science:

  • Crystallography and Structural Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Benzimidazole derivatives are important scaffolds in medicinal chemistry and materials science.
  • Understanding crystal structures provides insights into molecular behavior and potential applications.
  • Disorder in crystal structures can significantly influence bulk properties and reactivity.

Purpose of the Study:

  • To determine and analyze the crystal structures of three novel benzimidazole esters.
  • To investigate the nature and extent of molecular disorder in these compounds.
  • To correlate structural features, including disorder, with intermolecular interactions and packing motifs.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the three-dimensional structures.
  • Crystallographic data were analyzed to identify and quantify atomic site disorder.
  • Intermolecular interactions, such as hydrogen bonding and π-π stacking, were examined.

Main Results:

  • All three benzimidazole esters exhibited significant molecular disorder in their crystal structures.
  • Specific disordered units included prop-2-yn-1-oxyphenyl (I), propyl substituent (II), and ester unit (III).
  • Disorder affected the formation of continuous intermolecular networks, with C-H⋯π(arene) bonds in (I) bridging different disorder components.

Conclusions:

  • The crystal structures highlight the prevalence of disorder in substituted benzimidazole esters.
  • Molecular disorder influences the observed packing arrangements and intermolecular interactions.
  • These findings contribute to a deeper understanding of structure-property relationships in this class of compounds.