Chemistry - A European Journal, volume 23, issue 4, pages 852-864
New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction
Chulanova Elena A
1, 2, 3
,
Pritchina Elena A.
3
,
Malaspina Lorraine
4
,
Grabowsky Simon
4
,
Mostaghimi Farzin
4
,
Beckmann Jens
4
,
Bagryanskaya Irina Yu.
2, 3
,
Shakhova Margarita V
5
,
Konstantinova Lidia S.
6, 7
,
Rakitin Oleg A.
6, 7
,
Gritsan N.P
1, 5
,
Zibarev Andrey V.
2, 5
4
Institute for Inorganic Chemistry and Crystallography; University of Bremen; 28359 Bremen Germany
|
Publication type: Journal Article
Publication date: 2016-12-13
Journal:
Chemistry - A European Journal
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 4.3
ISSN: 09476539, 15213765
General Chemistry
Catalysis
Organic Chemistry
Abstract
The design and synthesis of novel charge-transfer (CT) complexes are of interest for fundamental chemistry and applications to materials science. In addition to the recently described first CT complex with both electron acceptor (A) and donor (D) groups belonging to the 1,2,5-thiadiazole series (1; A: 4-nitro-2,1,3-benzothiadiazole; D: 4-amino-2,1,3-benzothiadiazole), herein novel CT complexes 2 and 3 with 1,2,5-thiadiazoles as both A (4,6-dinitro-2,1,3-benzothiadiazole and [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole) and D (4-amino-2,1,3-benzothiadiazole) were synthesized. The series is completed by complex 4 with [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole as A and phenoxatellurine as D. Structures of complexes 2-4 were characterized by single-crystal X-ray diffraction (XRD), as well as solution and solid-state UV/Vis spectroscopy. Thermodynamics of their formation were obtained by density functional theory (DFT) calculations, their bonding situations were analyzed by quantum theory of atoms in molecules (QTAIM) calculations and dimer model energies of interactions quantified in the framework of the Hirshfeld surface (HS) analysis. With DFT calculations, the largest value of CT between D and A was found for complex 2, with 0.027 e in the XRD structure and 0.150 e in the optimized structure in MeCN. In the UV/Vis spectra, the λmax of the CT bands of 2-4 varied in the range λ=517-705 nm. Model energy calculations for 1-4 revealed the importance of both dispersion interactions and hydrogen bonding between D and A as contributors to CT in the crystalline state. In an attempt to enlarge the CT value with bis[1,2,5-thiadiazolo][3,4-b;3',4'-e]pyrazine as A and 4-amino-2,1,3-benzoselenadiazole as D, an unprecedented 1:1 addition reaction was observed upon formation of a C-N bond between atom C7 of D and pyrazine atom N4 of A, accompanied by hydrogen atom transfer from C7 to another pyrazine atom N8 (compound 5). According to DFT calculations, the reaction is a multistep process featuring diradical intermediates and hydrogen atom intramolecular migration over four positions. Molecular and crystal structures of 5 (solvate with toluene) were elucidated by XRD and the crystal structure revealed a rather unusual porous framework.
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Chulanova E. A. et al. New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction // Chemistry - A European Journal. 2016. Vol. 23. No. 4. pp. 852-864.
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Chulanova E. A., Pritchina E. A., Malaspina L., Grabowsky S., Mostaghimi F., Beckmann J., Bagryanskaya I. Y., Shakhova M. V., Konstantinova L. S., Rakitin O. A., Gritsan N., Zibarev A. V. New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction // Chemistry - A European Journal. 2016. Vol. 23. No. 4. pp. 852-864.
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TY - JOUR
DO - 10.1002/chem.201604121
UR - https://doi.org/10.1002%2Fchem.201604121
TI - New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction
T2 - Chemistry - A European Journal
AU - Pritchina, Elena A.
AU - Mostaghimi, Farzin
AU - Shakhova, Margarita V
AU - Konstantinova, Lidia S.
AU - Chulanova, Elena A
AU - Malaspina, Lorraine
AU - Grabowsky, Simon
AU - Beckmann, Jens
AU - Bagryanskaya, Irina Yu.
AU - Rakitin, Oleg A.
AU - Gritsan, N.P
AU - Zibarev, Andrey V.
PY - 2016
DA - 2016/12/13 00:00:00
PB - Wiley
SP - 852-864
IS - 4
VL - 23
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2016_Chulanova,
author = {Elena A. Pritchina and Farzin Mostaghimi and Margarita V Shakhova and Lidia S. Konstantinova and Elena A Chulanova and Lorraine Malaspina and Simon Grabowsky and Jens Beckmann and Irina Yu. Bagryanskaya and Oleg A. Rakitin and N.P Gritsan and Andrey V. Zibarev},
title = {New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction},
journal = {Chemistry - A European Journal},
year = {2016},
volume = {23},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002%2Fchem.201604121},
number = {4},
pages = {852--864},
doi = {10.1002/chem.201604121}
}
Cite this
MLA
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Chulanova, Elena A., et al. “New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction.” Chemistry - A European Journal, vol. 23, no. 4, Dec. 2016, pp. 852-864. https://doi.org/10.1002%2Fchem.201604121.