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Structural Connectivity of 18-Crown-6/H+/L-Tryptophan Non-Covalent Complexes in Gas Phase and in Solution: Delineating Host-Guest-Solvent Interactions in Solution from Gas Phase Structures
Version 1
: Received: 27 September 2023 / Approved: 27 September 2023 / Online: 28 September 2023 (09:52:07 CEST)
How to cite:
Oh, Y.; Oh, H.B.; Lee, S. Structural Connectivity of 18-Crown-6/H+/L-Tryptophan Non-Covalent Complexes in Gas Phase and in Solution: Delineating Host-Guest-Solvent Interactions in Solution from Gas Phase Structures. Preprints2023, 2023091879. https://doi.org/10.20944/preprints202309.1879.v1
Oh, Y.; Oh, H.B.; Lee, S. Structural Connectivity of 18-Crown-6/H+/L-Tryptophan Non-Covalent Complexes in Gas Phase and in Solution: Delineating Host-Guest-Solvent Interactions in Solution from Gas Phase Structures. Preprints 2023, 2023091879. https://doi.org/10.20944/preprints202309.1879.v1
Oh, Y.; Oh, H.B.; Lee, S. Structural Connectivity of 18-Crown-6/H+/L-Tryptophan Non-Covalent Complexes in Gas Phase and in Solution: Delineating Host-Guest-Solvent Interactions in Solution from Gas Phase Structures. Preprints2023, 2023091879. https://doi.org/10.20944/preprints202309.1879.v1
APA Style
Oh, Y., Oh, H.B., & Lee, S. (2023). Structural Connectivity of 18-Crown-6/H+/L-Tryptophan Non-Covalent Complexes in Gas Phase and in Solution: Delineating Host-Guest-Solvent Interactions in Solution from Gas Phase Structures. Preprints. https://doi.org/10.20944/preprints202309.1879.v1
Chicago/Turabian Style
Oh, Y., Han Bin Oh and Sungyul Lee. 2023 "Structural Connectivity of 18-Crown-6/H+/L-Tryptophan Non-Covalent Complexes in Gas Phase and in Solution: Delineating Host-Guest-Solvent Interactions in Solution from Gas Phase Structures" Preprints. https://doi.org/10.20944/preprints202309.1879.v1
Abstract
We investigate the structural correlation of non-covalent crown ether/H+/L-tryptophan (CR/TrpH+) host-guest complexes in the solution phase with those in the gas phase generated through electrospray ionization/mass spectrometry (ESI/MS) techniques. We perform quantum chemical calculations to determine their structures, relative Gibbs free energies, and infrared spectra. We compare the calculated infrared (IR) spectra with the IR multiphoton dissociation (IRMPD) spectra observed for the 18-Crown-6/TrpH+ complex by Polfer and co-workers [J. Phys. Chem. A 2013, 117, 1181−1188] for assigning the IR bands. We observe that the carboxyl group remains ‘naked’, lacking hydrogen bonding with the CR unit in the gas phase, and that this most stable conformer originates from the corresponding lowest Gibbs free energy structure in solution. Based on these findings, we propose that gas phase host-guest complexes directly correlate with those in solution, reinforcing the possibility of obtaining invaluable information about host-guest-solvent interactions in solution from the structure of the host-guest pair in the gas phase.
Keywords
host-guest; IRMPD; crown ether; tryptophan
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
