Halogen Bonds Formed between Substituted Imidazoliums and N Bases of Varying N-Hybridization
Abstract
:1. Introduction
2. Systems and Methods
3. Results
3.1. Geometries and Energetics
3.2. Underlying Electronic Structure Patterns
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Not available. |
Acid | Base | H | Cl | Br | I |
---|---|---|---|---|---|
ImZ+ | NH3 | 2.136 | 2.826 | 2.803 | 2.723 |
PhImZ+ | NH3 | 2.137 | 2.829 | 2.806 | 2.719 |
ImZ+ | NMe3 | 1.964 | 2.712 | 2.583 | 2.549 |
ImZ+ | MeN=CHMe | 2.081 | 2.773 | 2.708 | 2.603 |
PhImZ+ | MeN=CHMe | 2.087 | 2.774 | 2.712 | 2.595 |
ImZ+ | N≡CMe | 2.178 | 2.820 | 2.833 | 2.806 |
Acid | Base | H | Cl | Br | I |
---|---|---|---|---|---|
ImZ+ | NH3 | −11.07 | −8.42 | −10.71 | −15.13 |
PhImZ+ | NH3 | −10.87 | −8.32 | −10.56 | −15.00 |
ImZ+ | NMe3 | −13.36 | −9.13 | −12.81 | −19.60 |
ImZ+ | MeN=CHMe | −13.36 | −9.57 | −12.34 | −17.97 |
PhImZ+ | MeN=CHMe | −13.11 | −9.48 | −12.21 | −17.89 |
ImZ+ | N≡CMe | −14.27 | −10.15 | −11.66 | −14.69 |
Acid | Base | H | Cl | Br | I |
---|---|---|---|---|---|
ImZ+ | NH3 | −4.10 | −2.69 | −4.58 | −8.71 |
PhImZ+ | NH3 | −4.52 | −2.94 | −4.91 | −9.33 |
ImZ+ | NMe3 | −4.94 | −3.85 | −6.28 | −12.05 |
ImZ+ | MeN=CHMe | −5.01 | −3.21 | −5.07 | −9.38 |
PhImZ+ | MeN=CHMe | −5.54 | −3.42 | −5.45 | −10.13 |
ImZ+ | N≡CMe | −3.51 | −2.26 | −3.28 | −5.35 |
Acid | Base | H | Cl | Br | I |
---|---|---|---|---|---|
ImZ+ | NH3 | 4.83 | 5.34 | 4.21 | 1.10 |
PhImZ+ | NH3 | 4.84 | 4.68 | 4.31 | 0.62 |
ImZ+ | NMe3 | 6.08 | 5.59 | 4.69 | 0.09 |
ImZ+ | MeN=CHMe | 5.59 | 6.30 | 5.55 | 2.34 |
PhImZ+ | MeN=CHMe | 6.24 | 8.58 | 4.87 | 1.87 |
ImZ+ | N≡CMe | 5.30 | 5.16 | 4.38 | 4.63 |
Base | H | Cl | Br | I |
---|---|---|---|---|
NH3 | 0.0225 | 0.0180 | 0.0221 | 0.0314 |
NMe3 | 0.0325 | 0.0243 | 0.0383 | 0.0487 |
MeN=CHMe | 0.0242 | 0.0199 | 0.0271 | 0.0407 |
N≡CMe | 0.0173 | 0.0156 | 0.0179 | 0.0229 |
Lewis Acid | Vs,max | Lewis Base | Vs,min |
---|---|---|---|
ImH | 124.31 | NH3 | −38.02 |
ImCl | 97.14 | NMe3 | −32.12 |
ImBr | 100.35 | MeN=CHMe | −32.25 |
ImI | 110.91 | N≡CMe | −38.09 |
Base | H | Cl | Br | I |
---|---|---|---|---|
NH3 | 15.76 | 4.93 | 9.61 | 20.31 |
NMe3 | 15.10 | 5.97 | 16.74 | 32.73 |
MeN=CHMe | 12.64 | 4.69 | 11.04 | 26.78 |
N≡CMe | 7.97 | 2.76 | 5.35 | 11.03 |
Base | H | Cl | Br | I |
---|---|---|---|---|
NH3 | 0.015 | 0.006 | 0.016 | 0.048 |
NMe3 | 0.025 | 0.013 | 0.042 | 0.088 |
MeN=CHMe | 0.014 | 0.008 | 0.024 | 0.068 |
N≡CMe | 0.004 | 0.000 | 0.005 | 0.022 |
Base | H | Cl | Br | I |
---|---|---|---|---|
NH3 | −180.2 | −3.9 | −5.5 | −2.7 |
NMe3 | −375.9 | −11.8 | −16.9 | −7.9 |
MeN=CHMe | −169.4 | −7.7 | −6.7 | −7.8 |
N≡CMe | −28.8 | +0.8 | −0.8 | −2.2 |
Component | H | Cl | Br | I |
---|---|---|---|---|
ES | −14.70 | −12.53 | −16.98 | −28.33 |
EXCH | 12.52 | 19.68 | 36.27 | 65.83 |
IND | −5.25 | −10.92 | −24.02 | −60.36 |
DISP | −3.48 | −3.33 | −4.27 | −6.35 |
total | −10.92 | −7.11 | −9.00 | −29.21 |
© 2017 by the author. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
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Scheiner, S. Halogen Bonds Formed between Substituted Imidazoliums and N Bases of Varying N-Hybridization. Molecules 2017, 22, 1634. https://doi.org/10.3390/molecules22101634
Scheiner S. Halogen Bonds Formed between Substituted Imidazoliums and N Bases of Varying N-Hybridization. Molecules. 2017; 22(10):1634. https://doi.org/10.3390/molecules22101634
Chicago/Turabian StyleScheiner, Steve. 2017. "Halogen Bonds Formed between Substituted Imidazoliums and N Bases of Varying N-Hybridization" Molecules 22, no. 10: 1634. https://doi.org/10.3390/molecules22101634