Deciphering the Role of Noncovalent Interactions in the Conformations of Dibenzo-1,5-dichalcogenocines.
chalcogen bond
conformational analysis
noncovalent interaction
tellurium
σ-hole
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
04 2022
04 2022
Historique:
revised:
03
01
2022
received:
24
11
2021
pubmed:
2
2
2022
medline:
6
4
2022
entrez:
1
2
2022
Statut:
ppublish
Résumé
This work reports a combined experimental and theoretical study on the new dibenzo-1,5-ditellurocine 2-Te in order to get an overview on the parameters controlling conformational change and to explain the differences with sulfur and selenium analogues. The preference of the boat conformer over the chair one is revealed by DFT calculations. For 2-Te, a ΔG value of about 3 kJ/mol was calculated, close to the value measured by NMR (5 kJ/mol). However, DFT calculations with implicit solvation effects could not clearly establish the presence of an intramolecular Te…HC noncovalent interaction (NCI), as observed in the solid state. The Independent Gradient Model (IGM) methodology discloses an existent but probably not sufficiently discriminating Te…HC NCI. It also confirms that van der Waals interactions between phenyl rings is a source of stabilization of the boat conformer. Furthermore, electrostatic potential analysis suggests that chalcogen bonds between Te σ-holes and solvent might play an important role.
Identifiants
pubmed: 35103424
doi: 10.1002/cplu.202100518
doi:
Substances chimiques
Solvents
0
Selenium
H6241UJ22B
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202100518Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
F. Liu, H. Wang, K. N. Houk, Curr. Org. Chem. 2013, 17, 1470-1480.
J.-H. Ha, S. N. Loh, Chem. Eur. J. 2012, 18, 7984-7999;
G. G. Hammes, Biochemistry 2002, 41, 8221-8228.
A. Goulet-Hanssens, F. Eisenreich, S. Hecht, Adv. Mater. 2020, 32, 1905966;
F. Bigdeli, C. T. Lollar, A. Morsali, H.-C. Zhou, Angew. Chem. Int. Ed. 2020, 59, 46652-4669;
S. Beyazit in Switchable Bioelectronics (Ed.: O. Parlak), Jenny Stanford Publishing, New York, 2020, pp. 27-64.
P. C. Knipe, S. Thompson, A. D. Hamilton, Chem. Sci. 2015, 6, 1630-1639.
H. Wayment-Steele, M. Wu, M. Gotrik, R. Das, Methods Enzymol. 2019, 623, 417-450.
B. A. F. Le Bailly, J. Clayden, Chem. Commun. 2016, 52, 4852-4863.
K. W. Plaxco, H. T. Soh, Trends Biotechnol. 2011, 29, 1-5;
E. J. Lemieux, M. Leclerc in Conjugated Polyelectrolytes (Eds.: B. Liu, G. C. Bazan), Wiley-VCH, Weinheim, 2013, pp. 231-261.
R. Crossley, A. P. Downing, M. Nogradi., A. Braga de Oliveira, W. D. Ollis, I. O. Sutherland, J. C. S. Perkin 1 1973, No volume number for this journal 205-217;
D. Montecalvo, M. St-Jacques, R. Wasylishen, J. Am. Chem. 1973, 95, 2023-2024;
W. D. Ollis, J. E. Stoddart, I. O. Sutherland, Tetrahedron 1974, 30, 1903-1924;
M. L. Jimeno, I. Alkorta, J. Elguero, J. E. Anderson, R. M. Claramunt, J. L. Lavandera, New J. Chem. 1998, 22, 1079-1083;
I. Alkorta, J. Elguero, Struct. Chem. 2010, 21, 885-891.
J. Elguero, A. R. Katritzky, B. S. El-Osta, R. L. Harlow, S. H. Simonsen, J. Chem. Soc. Perkin Trans. 1, 1976, No volume number for this journal 312-315;
C. Foces-Foces, F. H. Cano, P. Cabildo, R. M. Claramunt, J. Elguero, Acta Crystallogr. Sect. C 1991, 47, 2583-2585;
P. Domiano, P. Cozzini, R. M. Claramunt, J. L. Lavandera, D. Sanz, J. Elguero, J. Chem. Soc. Perkin Trans. 2 1992, No volume number for this journal 1609-1620;
P. Cabildo, R. M. Claramunt, P. Cornago, J. L. Lavandera, D. Sanz, N. Jagerovic, M. L. Jimeno, J. Elguero, I. Gilles, J. L. Aubagnac, J. Chem. Soc. Perkin Trans. 2 1996, No volume number for this journal 701-711;
L. Kobryn, W. P. Henry, F. R. Fronczek, R. Sygula, Tetrahedron Lett. 2009, 50, 7124-7127.
R. M. Claramunt, J. L. Lavandera, D. Sanz, J. Elguero, M. L. Jimeno, Tetrahedron 1998, 54, 9569-9580.
W. Fu, T. M. Alam, J. Li, J. Bustamante, T. Lien, R. W. Adams, S. J. Teat, B. J. Stokes, W. Yang, Y. Liu, J. Q. Lu, J. Am. Chem. Soc. 2020, 142, 16651-16660.
F. Ishiwari, S. Miyake, K. Inoue, K. Hirose, T. Fukushima, A. Saeki, Asian J. Org. Chem. 2021, 10, 1377-1381.
M. Iwaoka, M. Tomoda, J. Am. Chem. Soc. 1994, 116, 4463-4464;
M. Iwaoka, H. Komatsu, M. Tomoda, Bull. Chem. Soc. Jpn. 1996, 69, 1825-1828.
T. Chivers, R. S. Laitinen, Chem. Soc. Rev. 2015, 44, 1725-1739.
A. Chand, H. S. Biswal, J. Indian Inst. Sci. 2020, 100, 77-100.
For C−H…Te interaction, see:
T. Steiner, J. Mol. Struct. 1998, 447, 39-42;
M. J. Poropudas, J. M. Rautiainen, R. Oilunkaniemi, R. S. Laitinen, Dalton Trans. 2016, 45, 17206-17215.
For Ne−H…Te interaction, see:
C. J. Warren, D. M. Ho, R. C. Haushalter, A. B. Bocarsly, J. Chem. Soc. Chem. Commun. 1994, 3, 361-363;
R. Chen, J. Zhou, X. Liu, F. Hu, L. An, Y. Kan, C. Xue, Inorg. Chem. Commun. 2013, 28, 55-59.
M. Ghosh, P. Panwaria, S. Tothadi, A. Das, S. Khan, Inorg. Chem. 2020, 59, 17811-17821.
T. L. Hill, J. Chem. Phys. 1948, 16, 399-404.
B. Jeziorski, R. Moszynski, K. Szalewicz, Chem. Rev. 1994, 94, 1887-1930;
K. Szalewicz, WIREs Comput. Mol. Sci. 2012, 2, 254-272.
K. Morokuma, J. Chem. Phys. 1971, 55, 1236-1244;
M. J. S. Philipps, T. Fox, C. S. Tautermann, C.-K. Skylaris, Chem. Soc. Rev. 2015, 44, 3177-3211.
R. M. Parrish, J. F. Gonthier, C. Corminboeuf, D. Sherrill, J. Chem. Phys. 2015, 143, 051103;
P. Su, Z. Chen, W. Wu, Chem. Phys. Lett. 2015, 635, 250-256.
M. A. Blanco, A. M. Pendas, E. Francisco, J. Chem. Theory Comput. 2005, 1, 1096-109.
C. Lefebvre, G. Rubez, H. Khartabil, J.-C. Boisson, J. Contreras-Garcia, E. Hénon, Phys. Chem. Chem. Phys. 2017, 19, 17928-17936;
C. Lefebvre, H. Khartabil, J.-C. Boisson, J. Contreras-Garcia, J.-P. Piquemal, E. Hénon, ChemPhysChem 2018, 19, 724-735.
W. J. M. van Tilborg, R. Plomp, Recl. Trav. Chim. Pays-Bas 1977, 96, 282-286;
E. Voigt, H. Meier, Angew. Chem. Int. Ed. 1976, 15, 117;
Angew. Chem. 1976, 88, 94;
K. Kanakarajan, H. Meier, J. Org. Chem. 1983, 48, 881-883;
H. Meier, J. Prakt. Chem. 1996, 338, 383-385.
S. Yamazaki, K. Kohgami, M. Okazaki, S. Yamabe, T. Arai, J. Org. Chem. 1989, 54, 240-243.
D. Shanks, H. Frisell, H. Ottosson, L. Engman, Org. Biomol. Chem. 2006, 4, 846-852.
R. Gleiter, G. Haberhauer, D. B. Werz, F. Rominger, C. Bleiholder, Chem. Rev. 2018, 118, 2010-2041.
C. Y. Legault, CYLview, 1.0b; University of Sherbrooke, 2009 (http://www.cylview.org);
Deposition Number 2108623 (for 2-Te) contains 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. Eyring, Chem. Rev. 1935, 17, 65-77;
D. G. Truhlar, B. C. Garrett, S. J. Klippenstein, J. Phys. Chem. 1996, 100, 12771-12800.
S. K. Wolff, T. Ziegler, E. van Lenthe, E. J. Baerends, J. Chem. Phys. 1999, 110, 7689-7698;
J. Autschbach, S. Zheng, Annu. Rep. NMR Spectrosc. 2009, 67, 1-95.
J. Autschbach, T. Ziegler, J. Chem. Phys. 2000, 113, 936-947.
M. Ernzerhof, G. Scuseria, J. Chem. Phys. 1999, 110, 5029-5036.
I. L. Rusakova, L. B. Krivdin, Mendeleev Commun. 2018, 28, 1-13.
M. R. Milovanović, M. Boucher, Y. Cornaton, S. D. Zarić, M. Pfeffer, J. Djukic, Eur. J. Inorg. Chem. 2021, 2021, 4690-4699.
R. F. W. Bader, In Atoms in Molecules: A Quantum Theory; Clarendon: Oxford, 1990.
L. J. Farrugia, C. Evans, D. Lentz, M. Roemer, J. Am. Chem. 2009, 131, 1251-1268;
M. Hamdaoui, C. Desrousseaux, H. Habbita, J.-P. Djukic, Organometallics 2017, 36, 4864-4882.
H. Khartabil, L. Doudet, I. Allart-Simon, M. Ponce-Vargas, S. Gérard, E. Hénon, Org. Biomol. Chem. 2020, 18, 6840-6848.
M. Ponce-Vargas, C. Lefebvre, J.-C. Boisson, E. Hénon, J. Chem. Inf. Model. 2020, 60, 268-278.
J. Klein, H. Khartabil, J.-C. Boisson, J. Contreras-Garcia, J.-P. Piquemal, E. Hénon, J. Phys. Chem. A 2020, 124, 1850-1860.
F. Würthner, J. Org. Chem. 2021, Not Yet available, 1021/acs.joc.1c00625.
J. S. Murray, P. Lane, T. Clark, P. Politzer, J. Mol. Model. 2007, 13, 1033-1038.
C. B. Aakeroy, D. L. Bryce, G. R. Desiraju, A. Frontera, A. C. Legon, F. Nicotra, K. Rissanen, S. Scheiner, G. Terraneo, P. Metrangolo, G. Resnati, Pure Appl. Chem. 2019, 91, 1889-1892.
K. T. Mahmudov, M. N. Kopylovich, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Dalton Trans. 2017, 46, 10121-10138;
L. Vogel, P. Wonner, S. M. Huber, Angew. Chem. Int. Ed. 2019, 58, 1880-1891;
Angew. Chem. 2019, 131, 1896-1907;
N. Biot, D. Bonifazi, Coord. Chem. Rev. 2020, 413, 213243.
P. Scilabra, G. Terraneo, G. Resnati, Acc. Chem. Res. 2019, 52, 1313-1324.
J. Y. C. Lim, P. D. Beer, Chem 2018, 4, 731-783.
J. Bamberger, F. Ostler, O. García Mancheño, ChemCatChem 2019, 11, 5198-5211;
M. Breugst, J. J. Koenig, Eur. J. Org. Chem. 2020, 2020, 5473-5487.
For recent examples from our group, see:
R. Weiss, E. Aubert, P. Peluso, S. Cossu, P. Pale, V. Mamane, Molecules 2019, 24, 4484;
R. Weiss, E. Aubert, P. Pale, V. Mamane, Angew. Chem. Int. Ed. 2021, 60, 19281-19286.
M. H. Kolář, P. Hobza, Chem. Rev. 2016, 116, 5155-5187.
T. Brinck, J. S. Murray, P. Politzer, Int. J. Quantum Chem. 1992, 44, 57-64.
L. Tian, F. Chen, J. Comput. Chem. 2012, 33, 580-592.
S. Kolb, G. A. Oliver, D. B. Werz, Angew. Chem. Int. Ed. 2020, 59, 22306-22310;
Angew. Chem. 2020, 132, 22490-22495;
M. Rodewald, J. M. Rautiainen, T. Niksch, H. Görls, R. Oilunkaniemi, W. Weigand, R. S. Laitinen, Chem. Eur. J. 2020, 26, 13806-13818.
M. R. Milovanović, Q. Dherbassy, J. Wencel-Delord, F. Colobert, S. D. Zarić, J.-P. Djukic, ChemPhysChem 2020, 21, 2136-2142.
G. Te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-967.
J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
E. Caldeweyher, S. Ehlert, A. Hansen, H. Neugebauer, S. Spicher, C. Bannwarth, S. Grimme, J. Chem. Phys. 2019, 150, 154122.
E. Van Lenthe, J. G. Snijder, E. J. Baerends, J. Chem. Phys. 1996, 105, 6505-6516.
E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1993, 99, 4597-4610;
E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1994, 101, 9783-9792;
E. van Lenthe, A. Ehlers, E. J. Baerends, J. Chem. Phys. 1999, 110, 8943-8953.
A. Klamt, G. Schüürmann, J. chem. Soc. Perkin Trans. 2 1993, No volume number for this journal 799-805;
A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235;
A. Klamt, V. Jonas, J. Chem. Phys. 1996, 105, 9972-9981.
M. Franchini, P. H. T. Philipsen, L. Visscher, J. Comput. Chem. 2013, 34, 1819-1827.
G. Henkelman, B. P. Uberuaga, H. Jonsson, J. Chem. Phys. 2000, 113, 9901-9904.
F. Neese, WIREs Comput. Mol. Sci. 2012, 2, 73-78.
F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
C. F. Macrae, I. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shields, J. S. Stevens, M. Towler, P. A. Wood, J. Appl. Crystallogr. 2020, 53, 226-235.
W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graph. 1996, 14, 33-38.