Highly Polar Insertion Complexes with Focused IR Spectra and Internal Field-Inhibited Isomerization.
IR spectroscopy
ab initio calculations
insertion
ion pairs
isomerization
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
11 2020
11 2020
Historique:
received:
15
09
2020
revised:
20
10
2020
entrez:
6
11
2020
pubmed:
7
11
2020
medline:
7
11
2020
Statut:
ppublish
Résumé
Complexes of a polar molecule (benzene trioxide) and alkali halide diatoms are predicted to form stable conformers through not only a common attachment, but also trapping the molecule between the counterions. Two possible low- and no-barrier routes of formation of such an insertion complex are identified, and stability and other properties of this and other conformers are analyzed, including polarity and charge distribution. Calculated IR spectra indicate a bright feature specific for the insertion complex, facilitating its reliable experimental detection. Isomerization of the ion-pair-trapped molecule shows a nonobvious inhibition effect (through an increased potential energy barrier) compared to the free molecule due to the reduction of its polarity in the isomerization. Formation of a flatter isomer, trioxonine, is clearly "reported" by a sharp alteration of the IR spectrum, distinguishable also from its variation for the nonreactive relaxation of the insertion complex into an attached one.
Identifiants
pubmed: 33155771
doi: 10.1002/cplu.202000626
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2438-2445Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
Q. He, G. I. Vargas-Zúñiga, S. H. Kim, S. K. Kim, J. L. Sessler, Chem. Rev. 2019, 119, 9753-9835.
I. Saha, K. H. Park, M. N. Han, S. K. Kim, V. M. Lynch, J. L. Sessler, C. H. Lee, Org. Lett. 2014, 16, 5414-5417.
J. R. Avileś-Moreno, G. Berden, J. Oomens, B. Martıńez-Haya, ChemPhysChem 2017, 18, 1324-1332.
G. K. S. Prakash, F. Wang, Z. Zhang, R. Haiges, M. Rahm, K. O. Christe, T. Mathew, G. A. Olah, Angew. Chem. Int. Ed. 2014, 53, 11575-11578;
Angew. Chem. 2014, 126, 11759-11762.
F. Y. Naumkin, Phys. Chem. Chem. Phys. 2008, 10, 6986-6990.
G. Kochhar, F. Y. Naumkin, New J. Chem. 2010, 34, 2932-2936.
B. Cochrane, F. Y. Naumkin, Chem. Phys. Lett. 2016, 643, 137-141.
C. Trujillo, G. Sanchez-Sanz, I. Alkorta, J. Elguero, J. Phys. Chem. A 2011, 115, 13124-13132.
F. Y. Naumkin, J. Phys. Chem. A 2017, 121, 4545-4551.
S. A. C. McDowell, Chem. Phys. Lett. 2016, 665, 105-110.
S. Kerr, F. Y. Naumkin, New J. Chem. 2017, 41, 13576-13584.
S. A. C. McDowell, Comput. Theor. Chem. 2017, 1108, 18-22.
I. Alkorta, F. Blanco, P. M. Deya, J. Elguero, C. Estarellas, A. Frontera, D. Quinonero, Theor. Chem. Acc. 2010, 126, 1-14.
A. Frontera, D. Quinonero, P. M. Deya, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011, 1, 440-459.
F. Y. Naumkin, D. J. Wales, ChemPhysChem. 2020, 21, 348-355.
P. Wang, P. Zhu, W. Wu, H. Kang, C. Ye, Phys. Chem. Chem. Phys. 1999, 1, 3519-3525.
N. Camaioni, R. Po, J. Phys. Chem. Lett. 2013, 4, 1821-1828.
S. Y. Leblebici, T. L. Chen, P. Olalde-Velasco, W. Yang, B. Ma, ACS Appl. Mater. Interfaces 2013, 5, 10105-10110.
A. C. Aragonès, N. L. Haworth, N. Darwish, S. Ciampi, N. J. Bloomfield, G. G. Wallace, I. Diez-Perez, M. L. Coote, Nature 2016, 531, 88-91.
X. Huang, C. Tang, J. Li, L.-C. Chen, J. Zheng, P. Zhang, J. Le, R. Li, X. Li, J. Liu, Y. Yang, J. Shi, Z. Chen, M. Bai, H.-L. Zhang, H. Xia, J. Cheng, Z.-Q. Tian, W. Hong, Sci. Adv. 2019, 5, eaaw3072.
F. Y. Naumkin, Phys. Chem. Chem. Phys. 2006, 8, 4402-4404.
B. E. Ziegler, M. Lecours, R. A. Marta, J. Featherstone, E. Fillion, W. S. Hopkins, V. Steinmetz, N. S. Keddie, D. O'Hagan, T. B. McMahon, J. Am. Chem. Soc. 2016, 138, 7460-7463.
K. L. Schuchardt, B. T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, T. L. Windus, J. Chem. Inf. Model. 2007, 47, 1045-1052.
M. Valiev, E. J. Bylaska, N. Govind, K. Kowalski, T. P. Straatsma, H. J. J. van Dam, D. Wang, J. Nieplocha, E. Apra, T. L. Windus, W. A. de Jong, Comput. Phys. Commun. 2010, 181, 1477-1489.
CRC Handbook of Chemistry and Physics, 88th edn, Ed. David R. Lide (NIST), CRC Press/Taylor & Francis Group, Boca Raton, FL, 2007.
NIST Chemistry WebBook, NIST Standard Ref. Database Number 69, Eds. P. J. Linstrom and W. G. Mallard, NIST, Gaithersburg MD, 20899, https://webbook.nist.gov/chemistry/.
A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
Spectral Database for Organic Compounds, SDBS, https://sdbs.db.aist.go.jp.
N. V. Tkachenko, Z.-M. Sun, A. I. Boldyrev, ChemPhysChem 2019, 20, 2060-2062.