Next Article in Journal
Behind the Looking-Glass: A Review on Human Symmetry Perception
Next Article in Special Issue
On the Importance of Clar Structures of Polybenzenoid Hydrocarbons as Revealed by the π-Contribution to the Electron Localization Function
Previous Article in Journal
SU(2) and SU(1,1) Approaches to Phase Operators and Temporally Stable Phase States: Applications to Mutually Unbiased Bases and Discrete Fourier Transforms
Previous Article in Special Issue
How to Find the Fries Structures for Benzenoid Hydrocarbons
Open AccessArticle

On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems

1
Department of Chemistry, Warsaw University of Life Sciences (SGGW), ul. Nowoursynowska 159c, 02-776 Warszawa, Poland
2
Interdisciplinary Department of Biotechnology, Warsaw University of Life Sciences (SGGW), ul. Nowoursynowska 166, 02-776 Warszawa, Poland
*
Author to whom correspondence should be addressed.
Symmetry 2010, 2(3), 1485-1509; https://doi.org/10.3390/sym2031485
Received: 31 December 2009 / Revised: 19 May 2010 / Accepted: 7 July 2010 / Published: 12 July 2010
(This article belongs to the Special Issue Aromaticity and Molecular Symmetry)
The HOMA (Harmonic Oscillator Model of Aromaticity) index, reformulated in 1993, has been very often applied to describe π-electron delocalization for mono- and polycyclic π-electron systems. However, different measures of π-electron delocalization were employed for the CC, CX, and XY bonds, and this index seems to be inappropriate for compounds containing heteroatoms. In order to describe properly various resonance effects (σ-π hyperconjugation, n-π conjugation, π-π conjugation, and aromaticity) possible for heteroatomic π-electron systems, some modifications, based on the original HOMA idea, were proposed and tested for simple DFT structures containing C, N, and O atoms. An abbreviation HOMED was used for the modified index. View Full-Text
Keywords: geometry-based index; π-electron delocalization; σ-π hyperconjugation; n-π conjugation; π-π conjugation; aromaticity; heteroatomic compounds; DFT geometry-based index; π-electron delocalization; σ-π hyperconjugation; n-π conjugation; π-π conjugation; aromaticity; heteroatomic compounds; DFT
Show Figures

Scheme 1

MDPI and ACS Style

Raczyńska, E.D.; Hallman, M.; Kolczyńska, K.; Stępniewski, T.M. On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems. Symmetry 2010, 2, 1485-1509. https://doi.org/10.3390/sym2031485

AMA Style

Raczyńska ED, Hallman M, Kolczyńska K, Stępniewski TM. On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems. Symmetry. 2010; 2(3):1485-1509. https://doi.org/10.3390/sym2031485

Chicago/Turabian Style

Raczyńska, Ewa D.; Hallman, Małgorzata; Kolczyńska, Katarzyna; Stępniewski, Tomasz M. 2010. "On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems" Symmetry 2, no. 3: 1485-1509. https://doi.org/10.3390/sym2031485

Find Other Styles

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Search more from Scilit
 
Search
Back to TopTop