Additional Reaction and Mechanism of Dicyanobenzene: Formation of Charge-Assisted Hydrogen Bond Networks

16 Pages Posted: 20 Oct 2020

See all articles by Jianping Guo

Jianping Guo

Xi'an Jiaotong University (XJTU), The Silk Road Institute of International and Comparative Law, Students

Donglin Shang

affiliation not provided to SSRN

Ruide Xue

affiliation not provided to SSRN

Lixia Ling

affiliation not provided to SSRN

Junping Han

affiliation not provided to SSRN

Aihong Li

affiliation not provided to SSRN

Nan Yang

Beijing Building Materials Academy of Science Research

Baojun Wang

affiliation not provided to SSRN

Shengdi Bai

affiliation not provided to SSRN

Abstract

The interaction of LiN(SiMe 3 ) 2 with one equivalent of 1,3- or 1,4-dicyanobenzene followed by the addition of one equivalent of chlorodiphenylphosphine and oxidation by hydrogen peroxide gave charge-assisted hydrogen bond supramolecular polymeric structure compounds of the general formula [ArC(NH 2 ) 2 ] + [Ph 2 PO 2 ] - (Ar = 3-cyanophenyl for 1 , 4-cyanophenyl for 2 ). These compounds, which are composed of a featured type of synthon, show the typical solid-state and film fluorescence. When the above reactions were carried out with half of an equivalent of 1,3-dicyanobenzene, compound 1 and ammonium diphenylphosphinate were produced; with half of an equivalent of 1,4-dicyanobenzene, compound 3 was obtained. A mechanism for the formation of compounds 1-3 was proposed. Results of DFT calculations suggested that the nucleophilic addition reaction to the second cyano group of the dicyanobenzene was a HOMO-controlled process.

Keywords: dicyanobenzene, addition reaction, charge assisted hydrogen bond, synthon, solid-state fluorescence

Suggested Citation

Guo, Jianping and Shang, Donglin and Xue, Ruide and Ling, Lixia and Han, Junping and Li, Aihong and Yang, Nan and Wang, Baojun and Bai, Shengdi, Additional Reaction and Mechanism of Dicyanobenzene: Formation of Charge-Assisted Hydrogen Bond Networks. Available at SSRN: https://ssrn.com/abstract=3715474

Jianping Guo (Contact Author)

Xi'an Jiaotong University (XJTU), The Silk Road Institute of International and Comparative Law, Students ( email )

28 Xianning West Road
Xi'an, Shaanxi 710049
China

Donglin Shang

affiliation not provided to SSRN

No Address Available

Ruide Xue

affiliation not provided to SSRN

No Address Available

Lixia Ling

affiliation not provided to SSRN

No Address Available

Junping Han

affiliation not provided to SSRN

No Address Available

Aihong Li

affiliation not provided to SSRN

No Address Available

Nan Yang

Beijing Building Materials Academy of Science Research

Beijing
China

Baojun Wang

affiliation not provided to SSRN

No Address Available

Shengdi Bai

affiliation not provided to SSRN

No Address Available

Do you have a job opening that you would like to promote on SSRN?

Paper statistics

Downloads
5
Abstract Views
28
PlumX Metrics