Additional reaction and mechanism of dicyanobenzene: Formation of amidinium or amidine compounds
•Two amidinium diphenylphosphinate compounds with one- or two-dimensional networks or the amidine compound were synthesized by the stoichiometric reaction or relative positions of the cyano groups of dicyanobenzene.•The structure of three compounds was determined by single crystal X-ray analysis.•Th...
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| Published in | Journal of molecular structure Vol. 1234; p. 130203 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier B.V
15.06.2021
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| Abstract | •Two amidinium diphenylphosphinate compounds with one- or two-dimensional networks or the amidine compound were synthesized by the stoichiometric reaction or relative positions of the cyano groups of dicyanobenzene.•The structure of three compounds was determined by single crystal X-ray analysis.•The addition reaction mechanism was suggested based on the results of experiments and DFT calculations.•Fluorescence study showed that compounds 1 and 2 are available photoluminescence solid material.
The interaction of LiN(SiMe3)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 amidinium diphenylphosphinate compounds of the general formula [ArC(NH2)2]+[Ph2PO2]− (Ar = 3-cyanophenyl for 1, 4-cyanophenyl for 2). These compounds, in which the polymeric networks are interconnected through 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 (1,4-phenylene-bis(N-diphenylphosphinato)amidine) 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 is a HOMO-controlled process.
The amidinium diphenylphosphinate compounds with one- or two-dimensional polymeric network which are interconnected through a featured type of synthon, show the typical solid-state and film fluorescence. [Display omitted] |
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| AbstractList | •Two amidinium diphenylphosphinate compounds with one- or two-dimensional networks or the amidine compound were synthesized by the stoichiometric reaction or relative positions of the cyano groups of dicyanobenzene.•The structure of three compounds was determined by single crystal X-ray analysis.•The addition reaction mechanism was suggested based on the results of experiments and DFT calculations.•Fluorescence study showed that compounds 1 and 2 are available photoluminescence solid material.
The interaction of LiN(SiMe3)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 amidinium diphenylphosphinate compounds of the general formula [ArC(NH2)2]+[Ph2PO2]− (Ar = 3-cyanophenyl for 1, 4-cyanophenyl for 2). These compounds, in which the polymeric networks are interconnected through 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 (1,4-phenylene-bis(N-diphenylphosphinato)amidine) 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 is a HOMO-controlled process.
The amidinium diphenylphosphinate compounds with one- or two-dimensional polymeric network which are interconnected through a featured type of synthon, show the typical solid-state and film fluorescence. [Display omitted] |
| ArticleNumber | 130203 |
| Author | Han, Junping Li, Aihong Shang, Donglin Xue, Ruide Ling, Lixia Bai, Shengdi Yang, Nan Wang, Baojun Guo, Jianping |
| Author_xml | – sequence: 1 givenname: Donglin surname: Shang fullname: Shang, Donglin organization: The Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, P. R. China – sequence: 2 givenname: Ruide surname: Xue fullname: Xue, Ruide organization: State Key Laboratory of Solid Waste Reuse for Building Materials, Beijing Building Materials Academy of Science Research, Beijing 100041, P. R. China – sequence: 3 givenname: Lixia surname: Ling fullname: Ling, Lixia organization: Key Laboratory of Coal Science & Technology, Ministry of Education and Shanxi Province, Taiyuan University of Technology, Taiyuan 030024, P. R. China – sequence: 4 givenname: Junping surname: Han fullname: Han, Junping organization: State Key Laboratory of Solid Waste Reuse for Building Materials, Beijing Building Materials Academy of Science Research, Beijing 100041, P. R. China – sequence: 5 givenname: Aihong surname: Li fullname: Li, Aihong organization: State Key Laboratory of Solid Waste Reuse for Building Materials, Beijing Building Materials Academy of Science Research, Beijing 100041, P. R. China – sequence: 6 givenname: Nan surname: Yang fullname: Yang, Nan organization: State Key Laboratory of Solid Waste Reuse for Building Materials, Beijing Building Materials Academy of Science Research, Beijing 100041, P. R. China – sequence: 7 givenname: Baojun surname: Wang fullname: Wang, Baojun organization: Key Laboratory of Coal Science & Technology, Ministry of Education and Shanxi Province, Taiyuan University of Technology, Taiyuan 030024, P. R. China – sequence: 8 givenname: Jianping orcidid: 0000-0001-7302-5493 surname: Guo fullname: Guo, Jianping email: guojianping@bmtbj.cn organization: State Key Laboratory of Solid Waste Reuse for Building Materials, Beijing Building Materials Academy of Science Research, Beijing 100041, P. R. China – sequence: 9 givenname: Shengdi surname: Bai fullname: Bai, Shengdi email: sdbai@sxu.edu.cn organization: The Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, P. R. China |
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| Title | Additional reaction and mechanism of dicyanobenzene: Formation of amidinium or amidine compounds |
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