Insight from electron density and energy framework analysis on the structural features of Fx-TCNQ (x = 0, 2, 4) family of molecules

Rahul Shukla; Christian  Ruzié; Guillaume Schweicher; Alan R. Kennedy; Yves H. Geerts; Deepak Chopra; Basab Chattopadhyay

doi:10.1107/S2052520618017109

Insight from electron density and energy framework analysis on the structural features of F_x-TCNQ (x = 0, 2, 4) family of molecules

Rahul Shukla, Christian Ruzié, Guillaume Schweicher, Alan R. Kennedy, Yves H. Geerts, Deepak Chopra, Basab Chattopadhyay

Pure And Applied Chemistry

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Abstract

In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. F_x-TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N≡C...F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

Original language	English
Pages (from-to)	71-78
Number of pages	8
Journal	Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume	75
Issue number	Part 1
DOIs	https://doi.org/10.1107/S2052520618017109
Publication status	Published - 28 Feb 2019

Keywords

fluorination
tetra-cyano-quino-dimethane
π-hole interaction
tetrel bond
electron density
energy framework
TCNQ
intermolecular interactions
charge density analysis

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Shukla-etal-ACSB-2018-Insight-from-electron-density-and-energy-framework-analysisFinal published version, 1.42 MB

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Shukla, R., Ruzié, C., Schweicher, G., Kennedy, A. R., Geerts, Y. H., Chopra, D., & Chattopadhyay, B. (2019). Insight from electron density and energy framework analysis on the structural features of F_x-TCNQ (x = 0, 2, 4) family of molecules. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 75(Part 1), 71-78. https://doi.org/10.1107/S2052520618017109

@article{983bbc21172946e8a8697fe44fa098ea,

title = "Insight from electron density and energy framework analysis on the structural features of Fx-TCNQ (x = 0, 2, 4) family of molecules",

abstract = "In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. Fx-TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N≡C...F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.",

keywords = "fluorination, tetra-cyano-quino-dimethane, π-hole interaction, tetrel bond, electron density, energy framework, TCNQ, intermolecular interactions, charge density analysis",

author = "Rahul Shukla and Christian Ruzi{\'e} and Guillaume Schweicher and Kennedy, {Alan R.} and Geerts, {Yves H.} and Deepak Chopra and Basab Chattopadhyay",

year = "2019",

month = feb,

day = "28",

doi = "10.1107/S2052520618017109",

language = "English",

volume = "75",

pages = "71--78",

journal = "Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials",

issn = "2052-5192",

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Shukla, R, Ruzié, C, Schweicher, G, Kennedy, AR, Geerts, YH, Chopra, D & Chattopadhyay, B 2019, 'Insight from electron density and energy framework analysis on the structural features of F_x-TCNQ (x = 0, 2, 4) family of molecules', Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, vol. 75, no. Part 1, pp. 71-78. https://doi.org/10.1107/S2052520618017109

Insight from electron density and energy framework analysis on the structural features of F_x-TCNQ (x = 0, 2, 4) family of molecules. / Shukla, Rahul; Ruzié, Christian ; Schweicher, Guillaume et al.

In: Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, Vol. 75, No. Part 1, 28.02.2019, p. 71-78.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Insight from electron density and energy framework analysis on the structural features of Fx-TCNQ (x = 0, 2, 4) family of molecules

AU - Shukla, Rahul

AU - Ruzié, Christian

AU - Schweicher, Guillaume

AU - Kennedy, Alan R.

AU - Geerts, Yves H.

AU - Chopra, Deepak

AU - Chattopadhyay, Basab

PY - 2019/2/28

Y1 - 2019/2/28

N2 - In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. Fx-TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N≡C...F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

AB - In this study, the nature and characteristics of the intramolecular and intermolecular interactions in crystal structures of the fluoro-substituted 7,7,8,8-tetracyanoquinodimethane (TCNQ) family of molecules, i.e. Fx-TCNQ (x = 0, 2, 4), are explored. The molecular geometry of the reported crystal structures is directly dependent on the degree of fluorination in the molecule, which consequently also results in the presence of an intramolecular N≡C...F—C π-hole tetrel bond. Apart from this, the energy framework analysis performed along the respective transport planes provides new insights into the energetic distribution in this class of molecules.

KW - fluorination

KW - tetra-cyano-quino-dimethane

KW - π-hole interaction

KW - tetrel bond

KW - electron density

KW - energy framework

KW - TCNQ

KW - intermolecular interactions

KW - charge density analysis

UR - https://journals.iucr.org/b/

U2 - 10.1107/S2052520618017109

DO - 10.1107/S2052520618017109

M3 - Article

VL - 75

SP - 71

EP - 78

JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

SN - 2052-5192

IS - Part 1

ER -

Insight from electron density and energy framework analysis on the structural features of F_x-TCNQ (x = 0, 2, 4) family of molecules

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