Thiourea-Based Tritopic Halogen-Bonding Acceptors.
X-ray diffraction
halogen bonding
isothiocyanates and thiocyanates
noncovalent interactions
thiourea-based receptors
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
02 May 2023
02 May 2023
Historique:
revised:
14
03
2023
received:
13
01
2023
medline:
16
3
2023
pubmed:
16
3
2023
entrez:
15
3
2023
Statut:
ppublish
Résumé
A series of thiourea-based tritopic receptor molecules were synthesized to be used as building blocks for halogen-bonded assemblies. Here, 16 new receptor molecules were synthesized from two different 2,4,6-trialkyl-1,3,5-tris(bromomethyl)benzene starting materials via tris(isothiocyanatomethyl)benzene intermediates. The alkyl substituents in the benzene ring proved to be important for isothiocyanate group formation instead of competing thiocyanate group. The synthesis route allowed us to synthesize the isothiocyanate intermediates and further the receptor molecules without the typically used and highly toxic thiophosgene. The synthesized receptor molecules were used to study their halogen-bond acceptor properties with diiodotetrafluorobenzene donors by single-crystal X-ray diffraction method. We were able to obtain five new crystal structures of halogen-bonded complexes, in which all receptors showed two to four accepted C-I⋅⋅⋅S halogen bonds. The observed halogen bonds were highly directional and showed large variation in C=S⋅⋅⋅I acceptor angles, indicating flexible acceptor properties of sulfur.
Identifiants
pubmed: 36920017
doi: 10.1002/asia.202300031
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300031Subventions
Organisme : Academy of Finland
ID : 310975
Organisme : Academy of Finland
ID : 314343
Organisme : Academy of Finland
ID : 335600
Organisme : University of Jyvaskyla
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
N. Akhtar, N. Pradhan, A. Saha, V. Kumar, O. Biswas, S. Dey, M. Shah, S. Kumar, D. Manna, Chem. Commun. 2019, 55, 8482-8485.
E. V. Beletskiy, X.-B. Wang, S. R. Kass, J. Phys. Chem. A 2016, 120, 8309-8316.
Z. Li, F.-Y. Wu, L. Guo, A.-F. Li, Y.-B. Jiang, J. Phys. Chem. B 2008, 112, 7071-7079.
V. Juste-Navarro, L. Prieto, I. Delso, R. Manzano, T. Tejero, E. Reyes, J. L. Vicario, P. Merino, Adv. Synth. Catal. 2017, 359, 4122-4128.
F. Topić, K. Rissanen, J. Am. Chem. Soc. 2016, 138, 6610-6616.
K. S. Eccles, R. E. Morrison, A. S. Sinha, A. R. Maguire, S. E. Lawrence, Cryst. Growth Des. 2015, 15, 3442-3451.
L. Happonen, J. M. Rautiainen, A. Valkonen, Cryst. Growth Des. 2021, 21, 3409-3419.
N. K. Beyeh, F. Pan, K. Rissanen, Angew. Chem. Int. Ed. 2015, 54, 7303-7307;
Angew. Chem. 2015, 127, 7411-7415.
O. Dumele, N. Trapp, F. Diederich, Angew. Chem. Int. Ed. 2015, 54, 12339-12344;
Angew. Chem. 2015, 127, 12516-12521.
L. Turunen, A. Peuronen, S. Forsblom, E. Kalenius, M. Lahtinen, K. Rissanen, Chem. Eur. J. 2017, 23, 11714-11718.
O. Dumele, B. Schreib, U. Warzok, N. Trapp, C. A. Schalley, F. Diederich, Angew. Chem. Int. Ed. 2017, 56, 1152-1157;
Angew. Chem. 2017, 129, 1172-1177.
G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, G. Terraneo, Chem. Rev. 2016, 116, 2478-2601.
R. Taylor, O. Kennard, W. Versichel, Acta Crystallogr. Sect. B 1984, 40, 280-288.
C. B. Aakeröy, C. L. Spartz, in Halogen Bonding I: Impact on Materials Chemistry and Life Sciences (Eds.: P. Metrangolo, G. Resnati), Springer International Publishing, Cham, 2015, 155-182.
P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. Int. Ed. 2008, 47, 6114-6127;
Angew. Chem. 2008, 120, 6206-6220.
R. Bertani, P. Sgarbossa, A. Venzo, F. Lelj, M. Amati, G. Resnati, T. Pilati, P. Metrangolo, G. Terraneo, Coord. Chem. Rev. 2010, 254, 677-695.
C. B. Aakeröy, T. K. Wijethunga, J. Desper, J. Mol. Struct. 2014, 1072, 20-27.
J. Teyssandier, K. S. Mali, S. de Feyter, ChemistryOpen 2020, 9, 225-241.
A. Mukherjee, S. Tothadi, G. R. Desiraju, Acc. Chem. Res. 2014, 47, 2514-2524.
R. Kampes, S. Zechel, M. D. Hager, U. S. Schubert, Chem. Sci. 2021, 12, 9275-9286.
M. Saccone, L. Catalano, J. Phys. Chem. B 2019, 123, 9281-9290.
R. S. Nunes, D. Vila-Viçosa, P. J. Costa, J. Am. Chem. Soc. 2021, 143, 4253-4267.
R. Wilcken, M. O. Zimmermann, A. Lange, A. C. Joerger, F. M. Boeckler, J. Med. Chem. 2013, 56, 1363-1388.
A. M. S. Riel, D. A. Decato, J. Sun, O. B. Berryman, Chem. Commun. 2022, 58, 1378-1381.
D. Bulfield, S. M. Huber, Chem. Eur. J. 2016, 22, 14434-14450.
J. S. Murray, P. Lane, P. Politzer, J. Mol. Model. 2009, 15, 723-729.
P. Politzer, J. S. Murray, T. Clark, Phys. Chem. Chem. Phys. 2013, 15, 11178-11189.
R. B. Walsh, C. W. Padgett, P. Metrangolo, G. Resnati, T. W. Hanks, W. T. Pennington, Cryst. Growth Des. 2001, 1, 165-175.
A. Crihfield, J. Hartwell, D. Phelps, R. B. Walsh, J. L. Harris, J. F. Payne, W. T. Pennington, T. W. Hanks, Cryst. Growth Des. 2003, 3, 313-320.
M. T. Messina, P. Metrangolo, W. Panzeri, E. Ragg, G. Resnati, Tetrahedron Lett. 1998, 39, 9069-9072.
K. Boubekeur, J.-L. Syssa-Magalé, P. Palvadeau, B. Schöllhorn, Tetrahedron Lett. 2006, 47, 1249-1252.
L. Koskinen, P. Hirva, E. Kalenius, S. Jääskeläinen, K. Rissanen, M. Haukka, CrystEngComm 2015, 17, 1231-1236.
A. Vanderkooy, A. K. Gupta, T. Földes, S. Lindblad, A. Orthaber, I. Pápai, M. Erdélyi, Angew. Chem. Int. Ed. 2019, 58, 9012-9016;
Angew. Chem. 2019, 131, 9110-9114.
L. Turunen, F. B. Németh, D. A. Decato, I. Pápai, O. B. Berryman, M. Erdélyi, Bull. Chem. Soc. Jpn. 2021, 94, 191-196.
L. Turunen, U. Warzok, R. Puttreddy, N. K. Beyeh, C. A. Schalley, K. Rissanen, Angew. Chem. Int. Ed. 2016, 55, 14033-14036;
Angew. Chem. 2016, 128, 14239-14242.
N. A. Esipenko, P. Koutnik, T. Minami, L. Mosca, V. M. Lynch, G. v. Zyryanov, P. Anzenbacher, Chem. Sci. 2013, 4, 3617-3623.
H. Valkenier, C. M. Dias, K. L. Porter Goff, O. Jurček, R. Puttreddy, K. Rissanen, A. P. Davis, Chem. Commun. 2015, 51, 14235-14238.
X. Wang, F. Hof, Beilstein J. Org. Chem. 2012, 8, 1-10.
M. C. Etter, J. C. MacDonald, J. Bernstein, Acta Crystallogr. Sect. B 1990, 46, 256-262.
C. R. Groom, F. H. Allen, Angew. Chem. Int. Ed. 2014, 53, 662-671;
Angew. Chem. 2014, 126, 675-684.
A. J. Peloquin, A. C. Ragusa, C. D. McMillen, W. T. Pennington, Acta Crystallogr. Sect. C 2021, 77, 599-609.
A. J. Peloquin, C. D. McMillen, S. T. Iacono, W. T. Pennington, ChemPlusChem 2021, 86, 549-557.
P. Cauliez, V. Polo, T. Roisnel, R. Llusar, M. Fourmigué, CrystEngComm 2010, 12, 558-566.
A. J. Peloquin, J. M. McCollum, C. D. McMillen, W. T. Pennington, Angew. Chem. Int. Ed. 2021, 60, 22983-22989;
Angew. Chem. 2021, 133, 23165-23171.
S. Watts, A. J. Peloquin, M. Bandara, C. D. McMillen, W. T. Pennington, Acta Crystallogr. Sect. C 2022, 78, 702-715.
A. C. Ragusa, A. J. Peloquin, M. M. Shahani, K. N. Dowling, J. A. Golen, C. D. McMillen, D. Rabinovich, W. T. Pennington, Acta Crystallogr. Sect. B: Struct. Sci., Cryst. Eng. Mater. 2022, 78, 745-755.
A. J. Peloquin, A. C. Ragusa, H. D. Arman, C. D. McMillen, W. T. Pennington, J. Chem. Crystallogr. 2022, 52, 512-524.
A. J. Peloquin, S. C. Hill, H. D. Arman, C. D. McMillen, D. Rabinovich, W. T. Pennington, J. Chem. Crystallogr. 2022, 52, 62-72.
K. M. Bairagi, K. S. Ingle, R. Bhowal, S. A. Mohurle, A. Hasija, O. I. Alwassil, K. N. Venugopala, D. Chopra, S. K. Nayak, ChemPlusChem 2021, 86, 1167-1176.
J. I. Jay, C. W. Padgett, R. D. B. Walsh, T. W. Hanks, W. T. Pennington, Cryst. Growth Des. 2001, 1, 501-507.
H. D. Arman, R. L. Gieseking, T. W. Hanks, W. T. Pennington, Chem. Commun. 2010, 46, 1854-1856.
N. Bricklebank, S. J. Coles, M. B. Hursthouse; 2003; 03SRC204; Crystal Structure Report Archive, University of Southampton; 10.5258/ecrystals/900.
Y. V. Torubaev, I. V. Skabitskiy, P. Rusina, A. A. Pasynskii, D. K. Rai, A. Singh, CrystEngComm 2018, 20, 2258-2266.
X. Ding, M. Tuikka, M. Haukka, Crystals 2020, 10, 165.
M. V. Chernysheva, J. M. Rautiainen, X. Ding, M. Haukka, J. Solid State Chem. 2021, 295, 121930.
U. Manna, B. Portis, T. K. Egboluche, M. Nafis, Md. A. Hossain, Front. Chem. 2021, 8, 575701.
E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley & Sons, Danvers, MA, 1994.
A. R. Kiasat, R. Badri, S. Sayyahi, Chin. Chem. Lett. 2008, 19, 1301-1304.
Y. Ren, M. Li, N.-B. Wong, S.-Y. Chu, J. Mol. Model. 2006, 12, 182-189.