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On Diphenalenes Comprising Seven Hexagonal Rings.

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Related Experiment Video

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Intra-Omental Islet Transplantation Using h-Omental Matrix Islet filliNG hOMING
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Three Queries about the HOMA Index.

Jan Cz Dobrowolski1

  • 1Institute of Nuclear Chemistry and Technology, 16 Dorodna Street, 03-195 Warsaw, Poland.

ACS Omega
|November 19, 2019
PubMed
Summary

The Harmonic Oscillator Model of Aromaticity (HOMA) is a reliable geometric index, but unlikely to be surpassed by benzene. New indices may offer alternatives but not necessarily superior aromaticity evaluation.

Area of Science:

  • Computational chemistry
  • Theoretical chemistry
  • Organic chemistry

Background:

  • The Harmonic Oscillator Model of Aromaticity (HOMA) is a widely used geometric index for assessing molecular aromaticity.
  • HOMA has a global maximum for benzene, unlike magnetic indices like NICS, raising questions about its limits and potential for higher aromaticity.
  • Existing definitions and comparisons with magnetic indices prompt re-evaluation of HOMA's scope and the development of alternative geometric indices.

Purpose of the Study:

  • To investigate if molecules with aromaticity greater than benzene exist beyond HOMA's definition.
  • To explore the viability of the cyclohexatriene moiety (HOMA=0) within larger molecular systems.
  • To assess the potential for improved geometrical aromaticity indices and compare them with HOMA.

Main Methods:

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  • Calculated HOMA and NICS indices for over 50 hexahomosubstituted benzenes.
  • Evaluated HOMA, EN, and GEO indices for over 100 triply fused hexasubstituted benzenes.
  • Assessed HOMA and a new Geometrical Auxiliary Index (GAI) for diverse hydrocarbons, including alkane constitutional isomers up to nine carbons.

Main Results:

  • Results suggest it is unlikely for a molecule to possess greater aromaticity than benzene according to HOMA.
  • The study questions the necessity of using cyclohexatriene as a reference for HOMA.
  • A new Geometrical Auxiliary Index (GAI) was introduced and compared with HOMA across various molecular structures.

Conclusions:

  • HOMA is a robust descriptor, but its upper limit suggests benzene's maximal aromaticity within its framework.
  • Alternative reference molecules for HOMA could be considered.
  • While new geometrical indices can be developed, their superiority in evaluating aromaticity over HOMA requires further validation.