Halogen Bonding Between Anions: Association of Anion Radicals of Tetraiodo-p-benzoquinone with Iodide Anions.
halides
halogen bonding
quinones
radical anions
supramolecular chemistry
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
21 Sep 2020
21 Sep 2020
Historique:
received:
25
03
2020
revised:
26
04
2020
pubmed:
5
6
2020
medline:
5
6
2020
entrez:
5
6
2020
Statut:
ppublish
Résumé
Halogen bonding between two negatively charged species, tetraiodo-p-benzoquinone anion radicals (I
Identifiants
pubmed: 32497382
doi: 10.1002/anie.202004384
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
17197-17201Subventions
Organisme : Division of Chemistry
ID : CHE-1607746
Organisme : Division of Chemistry
ID : CHE-1625543
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
Supramolecular Chemistry: From Molecules to Nanomaterials (Eds.: P. Gale, J. Steed), Wiley-VCH, Chichester, 2012.
C. A. Hunter, Angew. Chem. Int. Ed. 2004, 43, 5310-5324;
Angew. Chem. 2004, 116, 5424-5439;
A. Frontera, P. Gamez, M. Mascal, T. J. Mooibroek, J. Reedijk, Angew. Chem. Int. Ed. 2011, 50, 9564-9583;
Angew. Chem. 2011, 123, 9736-9756;
P. Politzer, J. S. Murray, T. Clark, Phys. Chem. Chem. Phys. 2013, 15, 11178-11189;
T. Clark, Faraday Discuss. 2017, 203, 9-27.
J.-M. Lü, S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2003, 125, 12161-12171;
M. Kertesz, Chem. Eur. J. 2019, 25, 400-416.
J. J. Novoa, P. Lafuente, R. E. Del Sesto, J. S. Miller, Angew. Chem. Int. Ed. 2001, 40, 2540-2545;
Angew. Chem. 2001, 113, 2608-2613;
S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2007, 129, 828-838.
N. G. White, CrystEngComm 2019, 21, 4855-4858;
R. Barbas, R. Prohens, A. Bauzá, A. Franconetti, A. Frontera, Chem. Commun. 2018, 55, 115-118.
Y.-H. Tian, M. Kertesz, J. Phys. Chem. A 2011, 115, 13942-13949;
M. Capdevila-Cortada, J. S. Miller, J. J. Novoa, Chem. Eur. J. 2014, 20, 7784-7795;
I. Garcia-Yoldi, J. S. Miller, J. J. Novoa, J. Phys. Chem. A 2009, 113, 484-492;
I. Garcia-Yoldi, J. S. Miller, J. J. Novoa, J. Phys. Chem. A 2007, 111, 8020-8027;
Y. Jung, M. Head-Gordon, Phys. Chem. Chem. Phys. 2004, 6, 2008-2011;
K. Molčanov, C. Jelsch, B. Landeros, J. Hernández-Trujillo, E. Wenger, V. Stilinović, B. Kojić-Prodić, E. C. Escudero-Adán, Cryst. Growth Des. 2019, 19, 391-402.
S. Khan, S. Roy, K. Harms, A. Bauzá, A. Frontera, S. Chattopadhyay, Inorg. Chim. Acta 2019, 487, 465-472;
Z. Chi, T. Yan, Q. Li, S. Scheiner, J. Phys. Chem. A 2019, 123, 7288-7295;
A. Gogoi, D. Dutta, A. K. Verma, H. Nath, A. Frontera, A. K. Guha, M. K. Bhattacharyya, Polyhedron 2019, 168, 113-126.
E. Corradi, S. V. Meille, M. T. Messina, P. Metrangolo, G. Resnati, Angew. Chem. Int. Ed. 2000, 39, 1782-1786;
Angew. Chem. 2000, 112, 1852-1856.
G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, A. G. Resnati, G. Terraneo, Chem. Rev. 2016, 116, 2478-2601;
L. C. Gilday, S. W. Robinson, T. A. Barendt, M. J. Langton, B. R. Mullaney, P. D. Beer, Chem. Rev. 2015, 115, 7118-7195;
S. Benz, A. I. Poblador-Bahamonde, N. Low-Ders, S. Matile, Angew. Chem. Int. Ed. 2018, 57, 5408-5412;
Angew. Chem. 2018, 130, 5506-5510.
C. Weinberger, R. Hines, M. Zeller, S. V. Rosokha, Chem. Commun. 2018, 54, 8060-8063;
R. Puttreddy, J. M. Rautiainen, T. Mäkelä, K. Rissanen, Angew. Chem. Int. Ed. 2019, 58, 18610-18618;
Angew. Chem. 2019, 131, 18783-18791.
M. Domagała, A. Lutyńska, M. Palusiak, J. Phys. Chem. A 2018, 122, 5484-5492;
J. Lieffrig, O. Jeannin, A. Frąckowiak, I. Olejniczak, R. Świetlik, S. Dahaoui, E. Aubert, E. Espinosa, P. Auban-Senzier, M. Fourmigué, Chem. Eur. J. 2013, 19, 14804-14813;
K. E. Riley, K.-A. Tran, Faraday Discuss. 2017, 203, 47-60;
M. Węcławik, A. Gągor, A. Piecha, R. Jakubas, W. Medycki, CrystEngComm 2013, 15, 5633-5640.
Note added in revisions:
In contrast to a large number of complexes of neutral or cationic XB donors with anions,[9, 12c] the only report of XB between different anions was published recently (after this work was submitted).[12b]
J. Holthoff, E. Engelage, R. Weiss, S. M. Huber, Angew. Chem. Int. Ed. 2020, 59, 11150-11157;
Angew. Chem. 2020, 132, 11244-11251;
P. H. Svensson, L. Kloo, Chem. Rev. 2003, 103, 1649-1684.
B. Rausch, M. D. Symes, L. J. Cronin, J. Am. Chem. Soc. 2013, 135, 13656-13659;
K. Ohkubo, A. Fujimoto, S. Fukuzumi, J. Am. Chem. Soc. 2013, 135, 5368-5371;
M. Cheng, X. Yang, F. Zhang, J. Zhao, L. Sun, Angew. Chem. Int. Ed. 2012, 51, 9896-9899;
Angew. Chem. 2012, 124, 10034-10037.
Y. Iida, Bull. Chem. Soc. Jpn. 1970, 43, 2772-2776;
J.-M. Lü, S. V. Rosokha, I. S. Neretin, J. K. Kochi, J. Am. Chem. Soc. 2006, 128, 16708-16719.
M. T. Huynh, C. W. Anson, A. C. Cavell, S. S. Stahl, S. Hammes-Schiffer, J. Am. Chem. Soc. 2016, 138, 15903-15910;
T. Kawashima, K. Ohkubo, S. Fukuzumi, Phys. Chem. Chem. Phys. 2011, 13, 3344-3362;
J. Datta, A. Bhattacharya, K. K. Kundu, Bull. Chem. Soc. Jpn. 1988, 61, 1735-1742.
S. Kepler, M. Zeller, S. V. Rosokha, J. Am. Chem. Soc. 2019, 141, 9338-9348.
K. Molčanov, G. Mali, J. Grdadolnik, J. Stare, V. Stilinović, B. Kojić-Prodić, Cryst. Growth Des. 2018, 18, 5182-5183.
A. Jalilov, S. Deats, M. Albukhari, M. Zeller, S. V. Rosokha, ChemPlusChem 2020, 85, 441-449.
Deposition Number(s) 1988834 (for (Et4N+)2I−⋅I4Q−.), and 1988835 (for (Fc*+)I4Q−.) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.
H. Kobayashi, T. Danno, I. Shirotani, Bull. Chem. Soc. Jpn. 1974, 47, 2333-2334.
A. Bondi, J. Phys. Chem. 1964, 68, 441-451;
R. D. Shannon, Acta Crystallogr. Sect. A 1976, 32, 751-767.
Y. Zhao, D. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241.
J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3093.
R. F. W. Bader, Chem. Rev. 1991, 91, 893-928.
The NCI index is the reduced density gradient s=|∇ρ|/(2(3π2)1/3)/ρ4/3), (where ρ is the electron density). An isosurface of s determines the spatial areas of the interaction, and the signs of the second eigenvalue of the density Hessian, sign(λ2)ρ, determines whether the interaction is bonding (λ2<0) or repulsive (λ2>0).[25b] The analysis was carried out and visualized using Multiwfn, VMD, and ASE programs.[25c-e]
E. R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras-García, A. J. Cohen, M. W. Yang, J. Am. Chem. Soc. 2010, 132, 6498-6506;
T. Lu, F. Chen, J. Comput. Chem. 2012, 33, 580-592;
W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graphics 1996, 14, 33-38;
A. H. Larsen, J. J. Mortensen, J. Blomqvist, I. E. Castelli, R. Christensen, M. Dulak, J. Friis, M. N. Groves, B. Hammer, C. Hargus, et al., J. Phys. Condens. Matter 2017, 29, 273002.
For example, DFT computations with acetonitrile as a medium showed that 2:2 complexes formed by linking of two I4Q−. radical anions via two I− anions are characterized by a ΔE of −2.8 kcal mol−1. The XB length (3.78 Å) in the 2:2 complexes (Figure S3) is higher than that in the corresponding 1:1 pair (3.74 Å). This might be one of the reasons of the differences between calculated and solid-state structural data.
Note that earlier works showed that more or less polar solvents represent the optimal medium for modelling intermolecular interactions in ionic solids.[11c]
Molecular-orbital interactions might also stabilize anion-anion bonding, as was suggested for other XB complexes. See:
R. J. Hach, R. E. Rundle, J. Am. Chem. Soc. 1951, 73, 4321-4324;
G. C. Pimentel, J. Chem. Phys. 1951, 19, 446;
S. M. Huber, E. Jimenez-Izal, J. M. Ugalde, I. Infante, Chem. Commun. 2012, 48, 7708;
S. V. Rosokha, C. L. Stern, J. T. Ritzert, Chem. Eur. J. 2013, 19, 8774;
M. Eraković, D. Cinčić, K. Molčanov, V. Stilinović, Angew. Chem. Int. Ed. 2019, 58, 15702;
Angew. Chem. 2019, 131, 15849.