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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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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 Compounds: Overview01:25

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
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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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Nomenclature of Aromatic Compounds with a Single Substituent01:23

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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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Aromatic Hydrocarbon Anions: Structural Overview01:18

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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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Basicity of Heterocyclic Aromatic Amines01:25

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Structure Elucidation of Pharmaceutically Relevant Compounds Within Pyrene-Based Frameworks.

Mohammad T Chaudhry1, Justin A Newman1, Alfred Y Lee1

  • 1Analytical Research and Development, Merck & Co., Inc., Rahway, New Jersey, 07065, United States of America.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 16, 2024
PubMed
Summary
This summary is machine-generated.

A new framework, tetrakis(guanidinium) pyrenetetrasulfonate (G4PYR), effectively encapsulates small molecules and active pharmaceutical ingredients (APIs) for structural analysis. This method aids in determining molecular structures when traditional crystallization fails.

Keywords:
CrystallographyPharmaceuticalsPyreneStructure elucidation

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Area of Science:

  • Materials Science
  • Crystallography
  • Supramolecular Chemistry

Background:

  • Single-crystal X-ray diffraction (SCXRD) is crucial for molecular structure determination but faces challenges with small molecules and APIs that resist crystallization.
  • Coformers are often required to obtain quality crystals, and some compounds may be unstable under standard crystallization conditions.

Purpose of the Study:

  • To introduce a novel guanidinium-organosulfonate (GS) framework, tetrakis(guanidinium) pyrenetetrasulfonate (G4PYR), for encapsulating challenging small molecules and APIs.
  • To demonstrate the utility of G4PYR in forming well-ordered hydrogen-bonded structures suitable for X-ray diffraction analysis.
  • To establish a workflow for investigating host-guest complex formation using powder X-ray diffraction and high-throughput experimentation.

Main Methods:

  • Synthesis and characterization of the tetrakis(guanidinium) pyrenetetrasulfonate (G4PYR) framework.
  • Encapsulation studies with various small molecules and active pharmaceutical ingredients (APIs).
  • Structural analysis using single-crystal X-ray diffraction (SCXRD) and powder X-ray diffraction (PXRD).
  • High-throughput experimentation for host-guest complex investigation.

Main Results:

  • G4PYR framework successfully encapsulates a range of functionalized small molecules (e.g., benzaldehyde, benzamide) and biologically relevant compounds (e.g., lidocaine, ropinirole, uracil, thymine, adenosine, thymidine).
  • The G4PYR framework forms well-ordered hydrogen-bonding networks with predictable pyrene-pyrene distances.
  • Demonstrated suitability for targeting arene-based APIs with pendant groups.
  • Developed and validated a workflow for host-guest complex formation studies.

Conclusions:

  • Tetrakis(guanidinium) pyrenetetrasulfonate (G4PYR) provides a robust platform for the structural determination of small molecules and APIs that are difficult to crystallize.
  • The G4PYR framework offers a promising strategy for coformer-free crystal engineering and structural analysis.
  • The presented workflow enables efficient investigation of host-guest complex formation, advancing drug discovery and materials science.