Use of an electron equivalent relationship between bond length and bond order to study chemical bonding. Part II. A study of bond orders, bond lengths and aromaticity in polycyclic aromatic hydrocarbons

József Emri, G. Lente

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Using the recently introduced concept of electron equivalent bond order, the characteristic bond orders of benzenoid hydrocarbons were studied based on experimental data. Fragmentation schemes can be used successfully to interpret the results and provide a very simple, consistent and useful valence bond approach for benzenoid hydrocarbons. The characteristic bond orders determined from experimental bond lengths can only assume eight discrete values in a relatively narrow range between 12/3 and 11/4 and primarily depend on the number of adjacent carbon-carbon bonds in the structure. The bond orders can also be used to define a quantitative scale of aromaticity for bonds, rings or entire molecules. A method, based on the optimization of quantified tendency toward maximum aromaticity and minimum octet-rule violation simultaneously, is also presented for the prediction of bond orders (and therefore bond lengths) of benzenoid hydrocarbons without any previous experimental information.

Original languageEnglish
Pages (from-to)211-219
Number of pages9
JournalJournal of Molecular Structure: THEOCHEM
Volume671
Issue number1-3
DOIs
Publication statusPublished - Feb 23 2004

Fingerprint

Chemical bonds
Polycyclic Aromatic Hydrocarbons
Bond length
polycyclic aromatic hydrocarbons
Polycyclic aromatic hydrocarbons
Hydrocarbons
hydrocarbons
Electrons
Carbon
electrons
carbon
octets
fragmentation
tendencies
valence
Molecules
optimization
rings
predictions
molecules

Keywords

  • Aromaticity scale
  • Benzenoid hydrocarbons
  • Bond fragmentation
  • Bond length/bond order prediction
  • Electron equivalent bond order

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

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abstract = "Using the recently introduced concept of electron equivalent bond order, the characteristic bond orders of benzenoid hydrocarbons were studied based on experimental data. Fragmentation schemes can be used successfully to interpret the results and provide a very simple, consistent and useful valence bond approach for benzenoid hydrocarbons. The characteristic bond orders determined from experimental bond lengths can only assume eight discrete values in a relatively narrow range between 12/3 and 11/4 and primarily depend on the number of adjacent carbon-carbon bonds in the structure. The bond orders can also be used to define a quantitative scale of aromaticity for bonds, rings or entire molecules. A method, based on the optimization of quantified tendency toward maximum aromaticity and minimum octet-rule violation simultaneously, is also presented for the prediction of bond orders (and therefore bond lengths) of benzenoid hydrocarbons without any previous experimental information.",
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N2 - Using the recently introduced concept of electron equivalent bond order, the characteristic bond orders of benzenoid hydrocarbons were studied based on experimental data. Fragmentation schemes can be used successfully to interpret the results and provide a very simple, consistent and useful valence bond approach for benzenoid hydrocarbons. The characteristic bond orders determined from experimental bond lengths can only assume eight discrete values in a relatively narrow range between 12/3 and 11/4 and primarily depend on the number of adjacent carbon-carbon bonds in the structure. The bond orders can also be used to define a quantitative scale of aromaticity for bonds, rings or entire molecules. A method, based on the optimization of quantified tendency toward maximum aromaticity and minimum octet-rule violation simultaneously, is also presented for the prediction of bond orders (and therefore bond lengths) of benzenoid hydrocarbons without any previous experimental information.

AB - Using the recently introduced concept of electron equivalent bond order, the characteristic bond orders of benzenoid hydrocarbons were studied based on experimental data. Fragmentation schemes can be used successfully to interpret the results and provide a very simple, consistent and useful valence bond approach for benzenoid hydrocarbons. The characteristic bond orders determined from experimental bond lengths can only assume eight discrete values in a relatively narrow range between 12/3 and 11/4 and primarily depend on the number of adjacent carbon-carbon bonds in the structure. The bond orders can also be used to define a quantitative scale of aromaticity for bonds, rings or entire molecules. A method, based on the optimization of quantified tendency toward maximum aromaticity and minimum octet-rule violation simultaneously, is also presented for the prediction of bond orders (and therefore bond lengths) of benzenoid hydrocarbons without any previous experimental information.

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