Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in p-CH3CH2COC6H4-C≡C-C≡C-p-C6H4COCH3CH2

The electron density of p-CH3CH2COC6H4-C≡CC≡C-p-C6H4COCH3CH2 has been investig...

Full description

Bibliographic Details
Main Authors:	Przemysław Starynowicz, Sławomir Berski, Nurbey Gulia, Karolina Osowska, Tadeusz Lis, Sławomir Szafert
Format:	Article
Language:	English
Published:	MDPI AG 2020-09-01
Series:	Molecules
Subjects:	polyynes density map single-crystal X-ray diffraction theoretical calculations electron localization function
Online Access:	https://www.mdpi.com/1420-3049/25/19/4388

id	doaj-8f1899bd33724164b2f1864b851dfce1
record_format	Article
spelling	doaj-8f1899bd33724164b2f1864b851dfce12020-11-25T03:19:03ZengMDPI AGMolecules1420-30492020-09-01254388438810.3390/molecules25194388Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>Przemysław Starynowicz0Sławomir Berski1Nurbey Gulia2Karolina Osowska3Tadeusz Lis4Sławomir Szafert5Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, PolandDepartment of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, PolandDepartment of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, PolandDepartment of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, PolandDepartment of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, PolandDepartment of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, PolandThe electron density of <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡CC≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub> has been investigated on the basis of single-crystal X-ray diffraction data collected to high resolution at 100 K and from theoretical calculations. An analysis of the X-ray data of the diyne showed interesting “liquidity” of electron distribution along the carbon chain compared to 1,2-diphenylacetylene. These findings are compatible with the results of topological analysis of Electron Localization Function (ELF), which has also revealed a larger (than expected) concentration of the electron density at the single bonds. Both methods indicate a clear π-type or “banana” character of a single bond and a significant distortion from the typical conjugated structure of the bonding in the diyne with a small contribution of cumulenic structures.https://www.mdpi.com/1420-3049/25/19/4388polyynesdensity mapsingle-crystal X-ray diffractiontheoretical calculationselectron localization function
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Przemysław Starynowicz Sławomir Berski Nurbey Gulia Karolina Osowska Tadeusz Lis Sławomir Szafert
spellingShingle	Przemysław Starynowicz Sławomir Berski Nurbey Gulia Karolina Osowska Tadeusz Lis Sławomir Szafert Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub> Molecules polyynes density map single-crystal X-ray diffraction theoretical calculations electron localization function
author_facet	Przemysław Starynowicz Sławomir Berski Nurbey Gulia Karolina Osowska Tadeusz Lis Sławomir Szafert
author_sort	Przemysław Starynowicz
title	Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>
title_short	Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>
title_full	Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>
title_fullStr	Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>
title_full_unstemmed	Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>
title_sort	is it conjugated or not? the theoretical and experimental electron density map of bonding in <i>p</i>-ch<sub>3</sub>ch<sub>2</sub>coc<sub>6</sub>h<sub>4</sub>-c≡c-c≡c-<i>p</i>-c<sub>6</sub>h<sub>4</sub>coch<sub>3</sub>ch<sub>2</sub>
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2020-09-01
description	The electron density of <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡CC≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub> has been investigated on the basis of single-crystal X-ray diffraction data collected to high resolution at 100 K and from theoretical calculations. An analysis of the X-ray data of the diyne showed interesting “liquidity” of electron distribution along the carbon chain compared to 1,2-diphenylacetylene. These findings are compatible with the results of topological analysis of Electron Localization Function (ELF), which has also revealed a larger (than expected) concentration of the electron density at the single bonds. Both methods indicate a clear π-type or “banana” character of a single bond and a significant distortion from the typical conjugated structure of the bonding in the diyne with a small contribution of cumulenic structures.
topic	polyynes density map single-crystal X-ray diffraction theoretical calculations electron localization function
url	https://www.mdpi.com/1420-3049/25/19/4388
work_keys_str_mv	AT przemysławstarynowicz isitconjugatedornotthetheoreticalandexperimentalelectrondensitymapofbondinginipichsub3subchsub2subcocsub6subhsub4subccccipicsub6subhsub4subcochsub3subchsub2sub AT sławomirberski isitconjugatedornotthetheoreticalandexperimentalelectrondensitymapofbondinginipichsub3subchsub2subcocsub6subhsub4subccccipicsub6subhsub4subcochsub3subchsub2sub AT nurbeygulia isitconjugatedornotthetheoreticalandexperimentalelectrondensitymapofbondinginipichsub3subchsub2subcocsub6subhsub4subccccipicsub6subhsub4subcochsub3subchsub2sub AT karolinaosowska isitconjugatedornotthetheoreticalandexperimentalelectrondensitymapofbondinginipichsub3subchsub2subcocsub6subhsub4subccccipicsub6subhsub4subcochsub3subchsub2sub AT tadeuszlis isitconjugatedornotthetheoreticalandexperimentalelectrondensitymapofbondinginipichsub3subchsub2subcocsub6subhsub4subccccipicsub6subhsub4subcochsub3subchsub2sub AT sławomirszafert isitconjugatedornotthetheoreticalandexperimentalelectrondensitymapofbondinginipichsub3subchsub2subcocsub6subhsub4subccccipicsub6subhsub4subcochsub3subchsub2sub
_version_	1724624054806118400

Is It Conjugated or Not? The Theoretical and Experimental Electron Density Map of Bonding in <i>p</i>-CH<sub>3</sub>CH<sub>2</sub>COC<sub>6</sub>H<sub>4</sub>-C≡C-C≡C-<i>p</i>-C<sub>6</sub>H<sub>4</sub>COCH<sub>3</sub>CH<sub>2</sub>

Similar Items