Remarkable electron accepting properties of the simplest benzenoid cyanocarbons: Hexacyanobenzene, octacyanonaphthalene and decacyanoanthracene

Xiuhui Zhang; Qianshu Li; Justin B. Ingels; Andrew C. Simmonett; Steven E. Wheeler; Yaoming Xie; R. Bruce King; Henry F. Schaefer; F. Albert Cotton

doi:10.1039/b515843e

Remarkable electron accepting properties of the simplest benzenoid cyanocarbons: Hexacyanobenzene, octacyanonaphthalene and decacyanoanthracene

Xiuhui Zhang
, Qianshu Li
, Justin B. Ingels
, Andrew C. Simmonett
, Steven E. Wheeler
, Yaoming Xie
, R. Bruce King
, Henry F. Schaefer^*
, F. Albert Cotton

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

21 Citations (Scopus)

Abstract

The optimised structures, electron affinities, and vibrational frequencies of the simplest benzenoid cyanocarbons, namely hexacyanobenzene C ₆(CN)₆, octacyanonaphthalene C₁₀(CN) ₈, and decacyanoanthracene C₁₄(CN)₁₀, have been studied using carefully calibrated density functional methods (Chem. Rev., 2002, 102, 231-282); the predicted adiabatic electron affinities are 3.53 eV for C₆(CN)₆, 4.35 eV for C₁₀(CN)₈ and 5.02 eV for C₁₄(CN)₁₀, which are significantly larger than those of the analogous benzenoid fluorocarbons as well as tetracyanoethane and tetracyanoquinodimethane.

Original language	English
Pages (from-to)	758-760
Number of pages	3
Journal	Chemical Communications
Issue number	7
DOIs	https://doi.org/10.1039/b515843e
Publication status	Published - 2006

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title = "Remarkable electron accepting properties of the simplest benzenoid cyanocarbons: Hexacyanobenzene, octacyanonaphthalene and decacyanoanthracene",

abstract = "The optimised structures, electron affinities, and vibrational frequencies of the simplest benzenoid cyanocarbons, namely hexacyanobenzene C 6(CN)6, octacyanonaphthalene C10(CN) 8, and decacyanoanthracene C14(CN)10, have been studied using carefully calibrated density functional methods (Chem. Rev., 2002, 102, 231-282); the predicted adiabatic electron affinities are 3.53 eV for C6(CN)6, 4.35 eV for C10(CN)8 and 5.02 eV for C14(CN)10, which are significantly larger than those of the analogous benzenoid fluorocarbons as well as tetracyanoethane and tetracyanoquinodimethane.",

author = "Xiuhui Zhang and Qianshu Li and Ingels, \{Justin B.\} and Simmonett, \{Andrew C.\} and Wheeler, \{Steven E.\} and Yaoming Xie and King, \{R. Bruce\} and Schaefer, \{Henry F.\} and Cotton, \{F. Albert\}",

year = "2006",

doi = "10.1039/b515843e",

language = "English",

pages = "758--760",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "7",

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TY - JOUR

T1 - Remarkable electron accepting properties of the simplest benzenoid cyanocarbons

T2 - Hexacyanobenzene, octacyanonaphthalene and decacyanoanthracene

AU - Zhang, Xiuhui

AU - Li, Qianshu

AU - Ingels, Justin B.

AU - Simmonett, Andrew C.

AU - Wheeler, Steven E.

AU - Xie, Yaoming

AU - King, R. Bruce

AU - Schaefer, Henry F.

AU - Cotton, F. Albert

PY - 2006

Y1 - 2006

N2 - The optimised structures, electron affinities, and vibrational frequencies of the simplest benzenoid cyanocarbons, namely hexacyanobenzene C 6(CN)6, octacyanonaphthalene C10(CN) 8, and decacyanoanthracene C14(CN)10, have been studied using carefully calibrated density functional methods (Chem. Rev., 2002, 102, 231-282); the predicted adiabatic electron affinities are 3.53 eV for C6(CN)6, 4.35 eV for C10(CN)8 and 5.02 eV for C14(CN)10, which are significantly larger than those of the analogous benzenoid fluorocarbons as well as tetracyanoethane and tetracyanoquinodimethane.

AB - The optimised structures, electron affinities, and vibrational frequencies of the simplest benzenoid cyanocarbons, namely hexacyanobenzene C 6(CN)6, octacyanonaphthalene C10(CN) 8, and decacyanoanthracene C14(CN)10, have been studied using carefully calibrated density functional methods (Chem. Rev., 2002, 102, 231-282); the predicted adiabatic electron affinities are 3.53 eV for C6(CN)6, 4.35 eV for C10(CN)8 and 5.02 eV for C14(CN)10, which are significantly larger than those of the analogous benzenoid fluorocarbons as well as tetracyanoethane and tetracyanoquinodimethane.

UR - https://www.scopus.com/pages/publications/32644481378

U2 - 10.1039/b515843e

DO - 10.1039/b515843e

M3 - Article

AN - SCOPUS:32644481378

SN - 1359-7345

SP - 758

EP - 760

JO - Chemical Communications

JF - Chemical Communications

IS - 7

ER -

Remarkable electron accepting properties of the simplest benzenoid cyanocarbons: Hexacyanobenzene, octacyanonaphthalene and decacyanoanthracene

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