Competition between Water–Water Hydrogen Bonds and Water–π Bonds in Pyrene–Water Cluster Anions

Salzmann, Heinrich; Rasmussen, Anne P.; Eaves, Joel D.; Weber, J. Mathias

doi:10.1021/acs.jpca.4c00997

Competition between Water–Water Hydrogen Bonds and Water–π Bonds in Pyrene–Water Cluster Anions

Journal Article · Tue Apr 02 00:00:00 EDT 2024 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.4c00997· OSTI ID:2339596

Salzmann, Heinrich ^[1]; Rasmussen, Anne P. ^[2]; ^[3]; ^[3]

University of Colorado, Boulder, CO (United States); University of Colorado Boulder
University of Colorado, Boulder, CO (United States); Aarhus University (Denmark)
University of Colorado, Boulder, CO (United States)

We present infrared spectra and density functional theory calculations of hydrated pyrene anion clusters with up to four water molecules. The experimental spectra were acquired using infrared Ar messenger photodissociation spectroscopy. Water molecules form clusters on the surface of the pyrene, forming hydrogen bonds with the pi-system. The structures of the water clusters and their interaction with the π-system are encoded in the OH stretching vibrational modes. Here, we find that the interactions between water molecules are stronger than they are between water molecules and the π-system. While all clusters show multiple conformers, three- and four-membered rings are the lowest energy structures in the larger hydrates.

View Accepted Manuscript (DOE)

Research Organization:: University of Colorado, Boulder, CO (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0021387

OSTI ID:: 2339596

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 14 Vol. 128; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (59)

Infrared Cavity Ringdown Spectroscopy of Jet-Cooled Polycyclic Aromatic Hydrocarbons Huneycutt, Alex J.; Casaes, Raphael N.; McCall, Benjamin J. ChemPhysChem, Vol. 5, Issue 3 https://doi.org/10.1002/cphc.200300776	journal	March 2004
An approach to computing electrostatic charges for molecules Singh, U. Chandra; Kollman, Peter A. Journal of Computational Chemistry, Vol. 5, Issue 2 https://doi.org/10.1002/jcc.540050204	journal	April 1984
Atomic charges derived from semiempirical methods Besler, Brent H.; Merz, Kenneth M.; Kollman, Peter A. Journal of Computational Chemistry, Vol. 11, Issue 4 https://doi.org/10.1002/jcc.540110404	journal	May 1990
A quadratically convergent Hartree—Fock (QC-SCF) method. Application to closed shell systems Bacskay, George B. Chemical Physics, Vol. 61, Issue 3 https://doi.org/10.1016/0301-0104(81)85156-7	journal	October 1981
First observation of ionic π-hydrogen bonds; vibrational spectroscopy of dihydrated naphthalene anion (Nph−(H2O)2) Kawamata, Hiroshi; Maeyama, Toshihiko; Mikami, Naohiko Chemical Physics Letters, Vol. 370, Issue 3-4 https://doi.org/10.1016/S0009-2614(03)00118-0	journal	March 2003
PAHs in the Fraser River basin: a critical appraisal of PAH ratios as indicators of PAH source and composition Yunker, Mark B.; Macdonald, Robie W.; Vingarzan, Roxanne Organic Geochemistry, Vol. 33, Issue 4 https://doi.org/10.1016/S0146-6380(02)00002-5	journal	April 2002
Cooperativity and hydrogen bonding network in water clusters Xantheas, Sotiris S. Chemical Physics, Vol. 258, Issue 2-3 https://doi.org/10.1016/S0301-0104(00)00189-0	journal	August 2000
Marine organic geochemistry of the Eastern Mediterranean: 1. Aliphatic and polyaromatic hydrocarbons in Cretan Sea surficial sediments Gogou, Alexandra; Bouloubassi, Ioanna; Stephanou, Euripides G. Marine Chemistry, Vol. 68, Issue 4 https://doi.org/10.1016/S0304-4203(99)00082-1	journal	February 2000
A wintertime study of PAHs in fine and coarse aerosols in São Paulo city, Brazil Bourotte, Christine; Forti, Maria-Cristina; Taniguchi, Satie Atmospheric Environment, Vol. 39, Issue 21 https://doi.org/10.1016/j.atmosenv.2005.02.054	journal	July 2005
Composition and sources of brown carbon aerosols in megacity Beijing during the winter of 2016 Li, Xingru; Zhao, Qing; Yang, Yang Atmospheric Research, Vol. 262 https://doi.org/10.1016/j.atmosres.2021.105773	journal	November 2021
Hydrogen bonding of the naphthalene radical cation to water and methanol and attachment of the naphthalene ion to extended hydrogen bonding chains Attah, Isaac K.; Platt, Sean P.; Meot-Ner (Mautner), Michael Chemical Physics Letters, Vol. 613 https://doi.org/10.1016/j.cplett.2014.08.035	journal	October 2014
A 150-year record of black carbon (soot and char) and polycyclic aromatic compounds deposition in Lake Phayao, north Thailand Han, Yongming; Bandowe, Benjamin A. Musa; Schneider, Tobias Environmental Pollution, Vol. 269 https://doi.org/10.1016/j.envpol.2020.116148	journal	January 2021
Laboratory experiments of Titan tholin formed in cold plasma at various pressures: implications for nitrogen-containing polycyclic aromatic compounds in Titan haze Imanaka, Hiroshi; Khare, Bishun N.; Elsila, Jamie E. Icarus, Vol. 168, Issue 2 https://doi.org/10.1016/j.icarus.2003.12.014	journal	April 2004
Refractory and semi-volatile organics at the surface of comet 67P/Churyumov-Gerasimenko: Insights from the VIRTIS/Rosetta imaging spectrometer Quirico, E.; Moroz, L. V.; Schmitt, B. Icarus, Vol. 272 https://doi.org/10.1016/j.icarus.2016.02.028	journal	July 2016
Comprehensive review of polycyclic aromatic hydrocarbons in water sources, their effects and treatments Mojiri, Amin; Zhou, John L.; Ohashi, Akiyoshi Science of The Total Environment, Vol. 696 https://doi.org/10.1016/j.scitotenv.2019.133971	journal	December 2019
Assessing Many-Body Effects of Water Self-Ions. I: OH ^– (H ₂ O) _n Clusters Egan, Colin K.; Paesani, Francesco Journal of Chemical Theory and Computation, Vol. 14, Issue 4 https://doi.org/10.1021/acs.jctc.7b01273	journal	March 2018
Anharmonicity and the IR Emission Spectrum of Neutral Interstellar PAH Molecules Mackie, Cameron J.; Candian, Alessandra; Lee, Timothy J. The Journal of Physical Chemistry A, Vol. 126, Issue 20 https://doi.org/10.1021/acs.jpca.2c01849	journal	May 2022
Exploring Expansions of the Potential and Dipole Surfaces Used for Vibrational Perturbation Theory McCoy, Anne B.; Boyer, Mark A. The Journal of Physical Chemistry A, Vol. 126, Issue 40 https://doi.org/10.1021/acs.jpca.2c05792	journal	October 2022
Water–Hydrocarbon Interactions in Anionic Pyrene Monohydrate LeMessurier, Natalie; Salzmann, Heinrich; Leversee, River The Journal of Physical Chemistry B, Vol. 128, Issue 13 https://doi.org/10.1021/acs.jpcb.3c07777	journal	March 2024
Effect of Microhydration on the Temporary Anion States of Pyrene Lietard, Aude; Verlet, Jan R. R. The Journal of Physical Chemistry Letters, Vol. 13, Issue 16 https://doi.org/10.1021/acs.jpclett.2c00523	journal	April 2022
Wetting of a Hydrophobic Surface: Far-IR Action Spectroscopy and Dynamics of Microhydrated Naphthalene Lemmens, Alexander K.; Ferrari, Piero; Loru, Donatella The Journal of Physical Chemistry Letters, Vol. 14, Issue 48 https://doi.org/10.1021/acs.jpclett.3c02854	journal	November 2023
Atomistic Hydrodynamics and the Dynamical Hydrophobic Effect in Porous Graphene Strong, Steven E.; Eaves, Joel D. The Journal of Physical Chemistry Letters, Vol. 7, Issue 10 https://doi.org/10.1021/acs.jpclett.6b00748	journal	May 2016
Accessing the Vibrational Signatures of Amino Acid Ions Embedded in Water Clusters Voss, Jonathan M.; Fischer, Kaitlyn C.; Garand, Etienne The Journal of Physical Chemistry Letters, Vol. 9, Issue 9 https://doi.org/10.1021/acs.jpclett.8b00738	journal	April 2018
Vibrational Spectroscopy of Microhydrated Conjugate Base Anions Asmis, Knut R.; Neumark, Daniel M. Accounts of Chemical Research, Vol. 45, Issue 1 https://doi.org/10.1021/ar2000748	journal	June 2011
Quantum Calculations of Vibrational Energies of H ₃ O ₂ ^- on an ab Initio Potential Huang, Xinchuan; Braams, Bastiaan J.; Carter, Stuart Journal of the American Chemical Society, Vol. 126, Issue 16 https://doi.org/10.1021/ja049801i	journal	April 2004
Infrared Spectroscopy of Hydrated Amino Acids in the Gas Phase: Protonated and Lithiated Valine Kamariotis, Anthi; Boyarkin, Oleg V.; Mercier, Sébastien R. Journal of the American Chemical Society, Vol. 128, Issue 3 https://doi.org/10.1021/ja056079v	journal	January 2006
Vibrational Spectroscopy of the Ionic Hydrogen Bond: Fermi Resonances and Ion−Molecule Stretching Frequencies in the Binary X ^- ·H ₂ O (X = Cl, Br, I) Complexes via Argon Predissociation Spectroscopy Ayotte, Patrick; Weddle, Gary H.; Kim, Jun Journal of the American Chemical Society, Vol. 120, Issue 47 https://doi.org/10.1021/ja981979f	journal	November 1998
Quantum Tunneling Facilitates Water Motion across the Surface of Phenanthrene Loru, Donatella; Steber, Amanda L.; Pérez, Cristóbal Journal of the American Chemical Society, Vol. 145, Issue 31 https://doi.org/10.1021/jacs.3c04281	journal	July 2023
Vibrational Spectroscopy for Size-Selected Fluorene−(H₂O)_n₌₁_,₂Clusters in Supersonic Jets Guchhait, Nikhil; Ebata, Takayuki; Mikami, Naohiko The Journal of Physical Chemistry A, Vol. 104, Issue 51 https://doi.org/10.1021/jp002958m	journal	November 2000
Laser Spectroscopy of Jet-Cooled Biomolecules and Their Water-Containing Clusters: Water Bridges and Molecular Conformation Zwier, Timothy S. The Journal of Physical Chemistry A, Vol. 105, Issue 39 https://doi.org/10.1021/jp011659+	journal	August 2001
The Tunable Hydrophobic Effect on Electrically Doped Graphene Ostrowski, Joseph H. J.; Eaves, Joel D. The Journal of Physical Chemistry B, Vol. 118, Issue 2 https://doi.org/10.1021/jp409342n	journal	January 2014
Nuclear Quantum Effects in the Reorientation of Water Paesani, Francesco; Yoo, Soohaeng; Bakker, Huib J. The Journal of Physical Chemistry Letters, Vol. 1, Issue 15 https://doi.org/10.1021/jz100734w	journal	July 2010
Wetting transparency of graphene Rafiee, Javad; Mi, Xi; Gullapalli, Hemtej Nature Materials, Vol. 11, Issue 3 https://doi.org/10.1038/nmat3228	journal	January 2012
Infrared spectroscopy of hydrated polycyclic aromatic hydrocarbon cations: naphthalene ⁺ –water Chatterjee, Kuntal; Dopfer, Otto Physical Chemistry Chemical Physics, Vol. 19, Issue 48 https://doi.org/10.1039/C7CP06893J	journal	January 2017
Microhydration of PAH ⁺ cations: evolution of hydration network in naphthalene ⁺ -(H ₂ O) _n clusters ( n ≤ 5) Chatterjee, Kuntal; Dopfer, Otto Chemical Science, Vol. 9, Issue 8 https://doi.org/10.1039/C7SC05124G	journal	January 2018
How does the composition of a PAH influence its microsolvation? A rotational spectroscopy study of the phenanthrene–water and phenanthridine–water clusters Loru, Donatella; Steber, Amanda L.; Pinacho, Pablo Physical Chemistry Chemical Physics, Vol. 23, Issue 16 https://doi.org/10.1039/D1CP00898F	journal	January 2021
Unravelling the microhydration frameworks of prototype PAH by infrared spectroscopy: naphthalene–(water)_1–3 Chatterjee, Kuntal; Roy, Tarun Kumar; Khatri, Jai Physical Chemistry Chemical Physics, Vol. 23, Issue 25 https://doi.org/10.1039/D1CP01789F	journal	January 2021
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Weigend, Florian; Ahlrichs, Reinhart Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305 https://doi.org/10.1039/b508541a	journal	January 2005
A high resolution dual mass gate for ion separation in laser desorption/ionization time of flight mass spectrometry Stoermer, Carsten W.; Gilb, Stefan; Friedrich, Jochen Review of Scientific Instruments, Vol. 69, Issue 4 https://doi.org/10.1063/1.1148823	journal	April 1998
Microsolvation of similar-sized aromatic molecules: Photoelectron spectroscopy of bithiophene–, azulene–, and naphthalene–water anion clusters Schiedt, J.; Knott, W. J.; Le Barbu, K. The Journal of Chemical Physics, Vol. 113, Issue 21 https://doi.org/10.1063/1.1319874	journal	December 2000
Large anharmonic effects in the infrared spectra of the symmetrical CH3NO2−⋅(H2O) and CH3CO2−⋅(H2O) complexes Myshakin, Evgeniy M.; Jordan, Kenneth D.; Sibert, Edwin L. The Journal of Chemical Physics, Vol. 119, Issue 19 https://doi.org/10.1063/1.1616918	journal	November 2003
Infrared spectroscopy of anionic hydrated fluorobenzenes Schneider, Holger; Vogelhuber, Kristen M.; Weber, J. Mathias The Journal of Chemical Physics, Vol. 127, Issue 11 https://doi.org/10.1063/1.2768348	journal	September 2007
Systematic optimization of long-range corrected hybrid density functionals Chai, Jeng-Da; Head-Gordon, Martin The Journal of Chemical Physics, Vol. 128, Issue 8 https://doi.org/10.1063/1.2834918	journal	February 2008
Microhydration effects on the electronic spectra of protonated polycyclic aromatic hydrocarbons: [naphthalene-(H ₂ O) _{n = 1,2} ]H ⁺ Alata, Ivan; Broquier, Michel; Dedonder-Lardeux, Claude The Journal of Chemical Physics, Vol. 134, Issue 7 https://doi.org/10.1063/1.3554416	journal	February 2011
Infrared vibrational predissociation spectroscopy of water clusters by the crossed laser-molecular beam technique Vernon, M. F.; Krajnovich, D. J.; Kwok, H. S. The Journal of Chemical Physics, Vol. 77, Issue 1 https://doi.org/10.1063/1.443631	journal	July 1982
Evaporative cooling Klots, Cornelius E. The Journal of Chemical Physics, Vol. 83, Issue 11 https://doi.org/10.1063/1.449615	journal	December 1985
Infrared spectroscopy of hydrated naphthalene cluster anions Knurr, Benjamin J.; Adams, Christopher L.; Weber, J. Mathias The Journal of Chemical Physics, Vol. 137, Issue 10 https://doi.org/10.1063/1.4750371	journal	September 2012
An infrared study of the competition between hydrogen-bond networking and ionic solvation: Halide-dependent distortions of the water trimer in the X−⋅(H2O)3, (X=Cl, Br, I) systems Ayotte, Patrick; Weddle, Gary H.; Johnson, Mark A. The Journal of Chemical Physics, Vol. 110, Issue 15 https://doi.org/10.1063/1.478616	journal	April 1999
Solvent-induced stabilization of the naphthalene anion by water molecules: A negative cluster ion photoelectron spectroscopic study Lyapustina, Svetlana A.; Xu, Shoujun; Nilles, J. Michael The Journal of Chemical Physics, Vol. 112, Issue 15 https://doi.org/10.1063/1.481237	journal	April 2000
The anharmonic quartic force field infrared spectra of five non-linear polycyclic aromatic hydrocarbons: Benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene Mackie, Cameron J.; Candian, Alessandra; Huang, Xinchuan The Journal of Chemical Physics, Vol. 145, Issue 8 https://doi.org/10.1063/1.4961438	journal	August 2016
Aqueous production of secondary organic aerosol from fossil-fuel emissions in winter Beijing haze Wang, Junfeng; Ye, Jianhuai; Zhang, Qi Proceedings of the National Academy of Sciences, Vol. 118, Issue 8 https://doi.org/10.1073/pnas.2022179118	journal	February 2021
Laboratory Determination of the Infrared band Strengths of Pyrene Frozen in Water ice: Implications for the Composition of Interstellar ices Hardegree-Ullman, E. E.; Gudipati, M. S.; Boogert, A. C. A. The Astrophysical Journal, Vol. 784, Issue 2 https://doi.org/10.1088/0004-637X/784/2/172	journal	March 2014
Model of molecular structure of the insoluble organic matter isolated from Murchison meteorite: Model of molecular structure of Murchison IOM Derenne, Sylvie; Robert, François Meteoritics & Planetary Science, Vol. 45, Issue 9 https://doi.org/10.1111/j.1945-5100.2010.01122.x	journal	September 2010
Spectral Signatures of Hydrated Proton Vibrations in Water Clusters Headrick, J. M. Science, Vol. 308, Issue 5729 https://doi.org/10.1126/science.1113094	journal	June 2005
Interplay of Intra- and Intermolecular H-Bonding in a Progressively Solvated Macrocyclic Peptide Nagornova, N. S.; Rizzo, T. R.; Boyarkin, O. V. Science, Vol. 336, Issue 6079 https://doi.org/10.1126/science.1218709	journal	April 2012
Interstellar Polycyclic Aromatic Hydrocarbon Molecules Tielens, A. G. G. M. Annual Review of Astronomy and Astrophysics, Vol. 46, Issue 1 https://doi.org/10.1146/annurev.astro.46.060407.145211	journal	September 2008
M OLECULAR A SPECTS OF H ALIDE I ON H YDRATION : The Cluster Approach Robertson, William H.; Johnson, Mark A. Annual Review of Physical Chemistry, Vol. 54, Issue 1 https://doi.org/10.1146/annurev.physchem.54.011002.103801	journal	October 2003
The Infrared Spectrum of Pyrene Anion in the CH Stretching Region Salzmann, Heinrich; McCoy, Anne B.; Weber, J. Mathias https://doi.org/10.26434/chemrxiv-2024-11xbh	preprint	February 2024
HIGH-RESOLUTION IR ABSORPTION SPECTROSCOPY OF POLYCYCLIC AROMATIC HYDROCARBONS IN THE 3 μ m REGION: ROLE OF PERIPHERY Maltseva, Elena; Petrignani, Annemieke; Candian, Alessandra The Astrophysical Journal, Vol. 831, Issue 1 https://doi.org/10.3847/0004-637x/831/1/58	journal	October 2016

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Competition between Water–Water Hydrogen Bonds and Water–π Bonds in Pyrene–Water Cluster Anions

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