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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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.
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
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Formation of Halohydrin from Alkenes02:41

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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.
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Aromatic interactions with heterocycles in water.

Gloria Tobajas-Curiel1, Qingqing Sun2,3, Jeremy K M Sanders1

  • 1Yusuf Hamied Department of Chemistry, University of Cambridge Cambridge CB2 1EW UK herchelsmith.orgchem@ch.cam.ac.uk.

Chemical Science
|October 20, 2023
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Summary

This study quantifies aromatic interactions in supramolecular complexes using calix[4]pyrrole receptors and pyridine N-oxide guests in water and chloroform. It reveals how solvent and heteroatoms influence binding, impacting molecular recognition.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • Supramolecular complexes offer a platform to study functional group interactions and solvation effects.
  • Understanding these interactions is crucial for designing selective molecular recognition systems.

Purpose of the Study:

  • To dissect and quantify the contributions of aromatic interactions to the stability of calix[4]pyrrole-heterocycle complexes.
  • To investigate the influence of solvent (water vs. chloroform) on these aromatic interactions.
  • To elucidate the role of heteroatoms within aromatic guests on binding affinity.

Main Methods:

  • Synthesis of four distinct calix[4]pyrrole receptors and eleven pyridine N-oxide guests.
  • Formation of 1:1 supramolecular complexes.
  • Characterization using proton nuclear magnetic resonance (¹H NMR) spectroscopy.
  • Quantification of interaction energies via chemical double mutant cycles.

Main Results:

  • Complex structures are stabilized by four hydrogen bonds, fixing aromatic interaction geometries.
  • In chloroform, aromatic interactions are similar to phenyl groups, with heteroatom position causing repulsion up to 8 kJ/mol.
  • In water, heterocycle interactions are more favorable (up to 12 kJ/mol), correlating with hydrophobicity for non-polar heterocycles.
  • Polar nitrogen atoms in guests form stabilizing water hydrogen bonds (approx. 15 kJ/mol).

Conclusions:

  • Solvation plays a complex role in molecular recognition in water.
  • Aromatic interactions are modulated by solvent polarity and the specific location of heteroatoms.
  • Calix[4]pyrrole-guest complexes provide a robust model for studying fundamental binding principles.