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Classical and Reverse Substituent Effects in Substituted Anthrol Derivatives.

Halina Szatylowicz1, Mateusz A Domanski1, Tadeusz M Krygowski2

  • 1Faculty of Chemistry Warsaw University of Technology Noakowskiego 3 00-664 Warsaw Poland.

Chemistryopen
|January 31, 2019
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Summary

This study investigates substituent effects in anthrols using quantum chemistry. It reveals mutual interdependencies between descriptors, highlighting both classical and reverse substituent influences.

Keywords:
anthrolaromaticitycomputational chemistryreverse substituent effectssubstituent effects

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Area of Science:

  • Organic Chemistry
  • Quantum Chemistry
  • Computational Chemistry

Background:

  • Anthrols are important organic compounds with diverse applications.
  • Understanding substituent effects is crucial for predicting and modifying molecular properties.
  • Previous studies have explored substituent effects in various aromatic systems.

Purpose of the Study:

  • To investigate the substituent effect in 1-, 2-, and 9-anthrols.
  • To analyze the interplay between substituents and the anthrol core using quantum chemical descriptors.
  • To characterize both classical and reverse substituent effects.

Main Methods:

  • Density Functional Theory (DFT) calculations using the B3LYP/6-311++G(d,p) level of theory.
  • Application of quantum chemistry-based descriptors: charge of the substituent active region (cSAR), substituent effect stabilization energy (SESE), and charge flow index (CFI).
  • Assessment of aromaticity using the HOMA index.

Main Results:

  • Established mutual interdependencies between various electronic descriptors (cSAR, SESE, CFI, and substituent constants σ).
  • Quantified the influence of substituents (NO2, CN, OH, NH2) on the anthrol system, particularly on the hydroxyl (OH) group.
  • Demonstrated the existence and significance of reverse substituent effects (influence of OH on the substituent) using the cSAR approach.

Conclusions:

  • The study provides a comprehensive understanding of substituent effects in anthrols.
  • Quantum chemical descriptors offer valuable insights into electronic interactions within substituted aromatic systems.
  • The findings contribute to the predictive modeling of chemical properties for substituted anthrols.