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Spectroscopic Measurement of a Halogen Bond Energy

Corresponding Author

Prof. Dr. Xinxing Zhang

[email protected]

orcid.org/0000-0001-5884-2727

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Dr. Gaoxiang Liu,

Dr. Gaoxiang Liu

Departments of Chemistry, Johns Hopkins University, Baltimore, MD, 21218 USA

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Sandra Ciborowski,

Sandra Ciborowski

Departments of Chemistry, Johns Hopkins University, Baltimore, MD, 21218 USA

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Wei Wang,

Wei Wang

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Chu Gong,

Chu Gong

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Yifan Yao,

Yifan Yao

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Prof. Dr. Kit Bowen,

Corresponding Author

Prof. Dr. Kit Bowen

[email protected]

orcid.org/0000-0002-2858-6352

Departments of Chemistry, Johns Hopkins University, Baltimore, MD, 21218 USA

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Prof. Dr. Xinxing Zhang,

Corresponding Author

Prof. Dr. Xinxing Zhang

[email protected]

orcid.org/0000-0001-5884-2727

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Dr. Gaoxiang Liu,

Dr. Gaoxiang Liu

Departments of Chemistry, Johns Hopkins University, Baltimore, MD, 21218 USA

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Sandra Ciborowski,

Sandra Ciborowski

Departments of Chemistry, Johns Hopkins University, Baltimore, MD, 21218 USA

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Wei Wang,

Wei Wang

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Chu Gong,

Chu Gong

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Yifan Yao,

Yifan Yao

Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education), Renewable Energy Conversion and Storage Center (ReCAST), College of Chemistry, Nankai University, Tianjin, 300071 China

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Prof. Dr. Kit Bowen,

Corresponding Author

Prof. Dr. Kit Bowen

[email protected]

orcid.org/0000-0002-2858-6352

Departments of Chemistry, Johns Hopkins University, Baltimore, MD, 21218 USA

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First published: 11 June 2019

https://doi.org/10.1002/anie.201906279

Citations: 17

Dedicated to the 100th anniversary of Nankai University

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Graphical Abstract

Strong noncovalent interaction: While halogen bonding has been widely recognized in many fields of chemistry, a benchmark spectroscopic measurement of its strength is still absent. Here, the strength of a poster child halogen bond between Br⁻ and CCl₃Br using anion photoelectron spectroscopy is reported.

Abstract

Halogen bonding (XB) has emerged as an important bonding motif in supramolecules and biological systems. Although regarded as a strong noncovalent interaction, benchmark measurements of the halogen bond energy are scarce. Here, a combined anion photoelectron spectroscopy and density functional theory (DFT) study of XB in solvated Br⁻ anions is reported. The XB strength between the positively-charged σ-hole on the Br atom of the bromotrichloromethane (CCl₃Br) molecule and the Br⁻ anion was found to be 0.63 eV (14.5 kcal mol⁻¹). In the neutral complexes, Br(CCl₃Br)_1,2, the attraction between the free Br atom and the negatively charged equatorial belt on the Br atom of CCl₃Br, which is a second type of halogen bonding, was estimated to have interaction strengths of 0.15 eV (3.5 kcal mol⁻¹) and 0.12 eV (2.8 kcal mol⁻¹).

Supporting Information

References

1P. Politzer, J. S. Murray, T. Clark, Phys. Chem. Chem. Phys. 2013, 15, 11178–11189.
10.1039/c3cp00054k
CAS PubMed Web of Science® Google Scholar
2P. Politzer, P. Lane, M. C. Concha, Y. Ma, J. S. Murray, J. Mol. Model. 2007, 13, 305–311.
10.1007/s00894-006-0154-7
CAS PubMed Web of Science® Google Scholar
3G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati, G. Terraneo, Chem. Rev. 2016, 116, 2478–2601.
10.1021/acs.chemrev.5b00484
CAS PubMed Web of Science® Google Scholar
4M. H. Kolář, P. Hobza, Chem. Rev. 2016, 116, 5155–5187.
10.1021/acs.chemrev.5b00560
CAS PubMed Web of Science® Google Scholar
5J.-M. Dumas, M. Kern, J. L. Janier-Dubry, Bull. Soc. Chim. Fr. 1976, 1785–1787.
CAS Web of Science® Google Scholar
6J.-M. Dums, H. Peurichard, M. J. Gomel, J. Chem. Res. Synop. 1978, 54–57.
Web of Science® Google Scholar
7T. Brinck, J. S. Murray, P. Politzer, Int. J. Quantum Chem. 1992, 44, 57–64.
10.1002/qua.560440709
Web of Science® Google Scholar
8T. Brinck, J. S. Murray, P. Politzer, Int. J. Quantum Chem. 1993, 48, 73–88.
10.1002/qua.560480202
CAS Web of Science® Google Scholar
9T. Clark, M. Hennemann, J. S. Murray, P. Politzer, J. Mol. Model. 2007, 13, 291–296.
10.1007/s00894-006-0130-2
CAS PubMed Web of Science® Google Scholar
10B. Li, S. Q. Zang, L. Y. Wang, T. C. Mak, Coord. Chem. Rev. 2016, 308, 1–21.
10.1016/j.ccr.2015.09.005
CAS Web of Science® Google Scholar
11R. Bertani, P. Sgarbossa, A. Venzo, F. Lelj, M. Amati, G. Resnati, T. Pilati, P. Metrangolo, G. Terraneo, Coord. Chem. Rev. 2010, 254, 677–695.
10.1016/j.ccr.2009.09.035
CAS Web of Science® Google Scholar
12V. Amico, S. V. Meille, E. Corradi, M. T. Messina, G. Resnati, J. Am. Chem. Soc. 1998, 120, 8261–8262.
10.1021/ja9810686
CAS Web of Science® Google Scholar
13P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo, Angew. Chem. Int. Ed. 2008, 47, 6114–6127;
10.1002/anie.200800128
CAS PubMed Web of Science® Google Scholar
Angew. Chem. 2008, 120, 6206–6220.
10.1002/ange.200800128
Web of Science® Google Scholar
14L. C. Gilday, S. W. Robinson, T. A. Barendt, M. J. Langton, B. R. Mullaney, P. D. Beer, Chem. Rev. 2015, 115, 7118–7195.
10.1021/cr500674c
CAS PubMed Web of Science® Google Scholar
15M. R. Scholfield, C. M. V. Zanden, M. Carter, P. S. Ho, Protein Sci. 2013, 22, 139–152.
10.1002/pro.2201
CAS PubMed Web of Science® Google Scholar
16D. Cappelletti, P. Candori, F. Pirani, L. Belpassi, F. Tarantelli, Cryst. Growth Des. 2011, 11, 4279–4283.
10.1021/cg200890h
CAS Web of Science® Google Scholar
17S. L. Stephens, N. R. Walker, A. C. Legon, J. Chem. Phys. 2011, 135, 224309.
10.1063/1.3664314
CAS PubMed Web of Science® Google Scholar
18H. I. Bloemink, J. H. Holloway, A. C. Legon, Chem. Phys. Lett. 1996, 254, 59–68.
10.1016/0009-2614(96)00184-4
CAS Web of Science® Google Scholar
19C. Domene, P. W. Fowler, A. C. Legon, Chem. Phys. Lett. 1999, 309, 463–470.
10.1016/S0009-2614(99)00736-8
CAS Web of Science® Google Scholar
20E. A. Gillis, M. Demireva, M. G. Sarwar, M. G. Chudzinski, M. S. Taylor, E. R. Williams, T. D. Fridgen, Phys. Chem. Chem. Phys. 2013, 15, 7638–7647.
10.1039/c3cp00105a
CAS PubMed Web of Science® Google Scholar
21A. C. Pearcy, K. A. Mason, M. S. El-Shall, J. Phys. Chem. A 2019, 123, 1363–1371.
10.1021/acs.jpca.8b09094
CAS PubMed Web of Science® Google Scholar
22X. Zhang, G. Liu, S. Ciborowski, K. Bowen, Angew. Chem. Int. Ed. 2017, 56, 9897–9900;
10.1002/anie.201705738
CAS PubMed Web of Science® Google Scholar
Angew. Chem. 2017, 129, 10029–10032.
10.1002/ange.201705738
Web of Science® Google Scholar
23M. Jabłoński, M. Palusiak, J. Phys. Chem. A 2012, 116, 2322–2332.
10.1021/jp211606t
CAS PubMed Web of Science® Google Scholar
24Y. X. Lu, J. W. Zou, Y. H. Wang, Y. J. Jiang, Q. S. Yu, J. Phys. Chem. A 2007, 111, 10781–10788.
10.1021/jp0740954
CAS PubMed Web of Science® Google Scholar
25S. H. Jungbauer, S. Schindler, E. Herdtweck, S. Keller, S. M. Huber, Chem. Eur. J. 2015, 21, 13625–13636.
10.1002/chem.201502043
CAS PubMed Web of Science® Google Scholar
26R. Li, Q. Li, J. Cheng, Z. Liu, W. Li, ChemPhysChem 2011, 12, 2289–2295.
10.1002/cphc.201100237
CAS PubMed Web of Science® Google Scholar
27A. Bauzá, I. Alkorta, A. Frontera, J. Elguero, J. Chem. Theory Comput. 2013, 9, 5201–5210.
10.1021/ct400818v
CAS PubMed Web of Science® Google Scholar
28P. Politzer, J. S. Murray, CrystEngComm 2013, 15, 3145–3150.
10.1039/c2ce26883c
CAS Web of Science® Google Scholar
29P. Politzer, J. S. Murray, ChemPhysChem 2013, 14, 278–294.
10.1002/cphc.201200799
CAS PubMed Web of Science® Google Scholar
30C. E. Moore, Natl. Stand. Ref. Data Ser. (U.S. Natl. Bur. Stand.) 1971, NSRDS-NBS 35, 208.
Google Scholar
31A. Ding, J. Hesslich, Chem. Phys. Lett. 1983, 94, 54–57.
10.1016/0009-2614(83)87209-1
CAS Web of Science® Google Scholar
32A. T. Droege, P. C. Engelking, Chem. Phys. Lett. 1983, 96, 316–318.
10.1016/0009-2614(83)80680-0
CAS Web of Science® Google Scholar

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Volume58, Issue33

August 12, 2019

Pages 11400-11403

Spectroscopic Measurement of a Halogen Bond Energy

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Spectroscopic Measurement of a Halogen Bond Energy

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Supporting Information

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