Vibrational spectroscopy of the cryogenically cooled O- and N-protomers of 4-aminobenzoic acid: Tag effects, isotopic labels, and identification of the E,Z isomer of the O-protomer

Akberova, 2002, New biological properties of p-aminobenzoic acid, Biol. Bull. (Woods Hole), 29, 390 Kratky, 2020, 4-Aminobenzoic acid derivatives: converting folate precursor to antimicrobial and cytotoxic agents, Biomolecules, 10 Sowinska, 2019, Molecular antioxidant properties and in vitro cell toxicity of the p-aminobenzoic acid (PABA) functionalized peptide dendrimers, Biomolecules, 9, 10.3390/biom9030089 Patel, 2019, Quinoxaline-PABA bipartite hybrid derivatization approach: design and search for antimicrobial agents, J. Mol. Struct., 1184, 562, 10.1016/j.molstruc.2019.02.074 Kadhum, 2016, Usefulness of liquid-crystal oral formulations to enhance the bioavailability and skin tissue targeting of p-amino benzoic acid as a model compound, Eur. J. Pharmaceut. Sci., 88, 282, 10.1016/j.ejps.2016.04.003 Kluczyk, 2002, Drug evolution: p-aminobenzoic acid as a building block, Curr. Med. Chem., 9, 1871, 10.2174/0929867023368872 Valverde, 2020, Carbon/inorganic hybrid nanoarchitectures as carriers for signaling elements in electrochemical immunosensors: first biosensor for the determination of the inflammatory and metastatic processes biomarker RANK-ligand, Chemelectrochem, 7, 10.1002/celc.201902025 S.N. Karri, S.P. Ega, P. Srinivasan, Synthesis of Novel Fluorescent Molecule and its Polymeric Form with Aniline as Fluorescent and Supercapacitor Electrode Materials, Polym Advan Technol, (n/a). Santos, 2020, A new tool for dengue virus diagnosis: optimization and detection of anti-NS1 antibodies in serum samples by impedimetric transducers, Microchem. J., 154, 104544, 10.1016/j.microc.2019.104544 Zhang, 2000, Thermodynamics of macroscopic and microscopic proton ionization from protonated 4-aminobenzoic acid in aqueous solution from 298.15 to 393.15 K, J. Phys. Chem. B, 104, 8598, 10.1021/jp994379r Tian, 2009, Gas-phase versus liquid-phase structures by electrospray ionization mass spectrometry, Angew. Chem. Int. Ed., 48, 1321, 10.1002/anie.200805392 Seo, 2016, The impact of environment and resonance effects on the site of protonation of aminobenzoic acid derivatives, Phys. Chem. Chem. Phys., 18, 25474, 10.1039/C6CP04941A Cismesia, 2017, Amine vs. carboxylic acid protonation in ortho-, meta-, and para-aminobenzoic acid: an IRMPD spectroscopy study, J. Mol. Spectrosc., 332, 79, 10.1016/j.jms.2016.10.020 Tian, 2009, Gas-phase versus liquid-phase structures by electrospray ionization mass spectrometry, Angew Chem. Int. Ed. Engl., 48, 1321, 10.1002/anie.200805392 Hebert, 2020, Tracking the structural evolution of 4-aminobenzoic acid in the transition from solution to the gas phase, J. Phys. Chem. B, 124, 2081, 10.1021/acs.jpcb.9b10576 Schmidt, 2011, Infrared multiphoton dissociation spectroscopy study of protonated p-aminobenzoic acid: does electrospray ionization afford the amino- or carboxy-protonated ion?, J. Phys. Chem., 115, 7625, 10.1021/jp203829z Davies, 2019, Probing elusive cations: infrared spectroscopy of protonated acetic acid, J. Phys. Chem. Lett., 10, 2108, 10.1021/acs.jpclett.9b00767 Spieler, 2018, Vibrational predissociation spectroscopy of cold protonated tryptophan with different messenger tags, J. Phys. Chem., 122, 8037, 10.1021/acs.jpca.8b07532 Menges, 2019, Integration of high-resolution mass spectrometry with cryogenic ion vibrational spectroscopy, J. Am. Soc. Mass Spectrom., 30, 1551, 10.1007/s13361-019-02238-y Yang, 2017, Isolation of site-specific anharmonicities of individual water molecules in the I¯·(H2O)2 complex using tag-free, isotopomer selective IR-IR double resonance, Chem. Phys. Lett., 690, 159, 10.1016/j.cplett.2017.09.042 Frisch, 2009 Chang, 2012, Where’s the charge? Protonation sites in gaseous ions change with hydration, J. Am. Chem. Soc., 134, 15805, 10.1021/ja304929h Fischer, 2020, Competition between solvation and intramolecular hydrogen-bonding in microsolvated protonated Glycine and beta-alanine, J. Phys. Chem., 124, 1593, 10.1021/acs.jpca.9b11977 Leavitt, 2011, Characterizing the intramolecular H-bond and secondary structure in methylated GlyGlyH+ with H2 predissociation spectroscopy, J. Am. Soc. Mass Spectrom., 22, 1941, 10.1007/s13361-011-0228-3 Voss, 2018, Accessing the vibrational signatures of amino acid ions embedded in water clusters, J. Phys. Chem. Lett., 9, 2246, 10.1021/acs.jpclett.8b00738 Johnson, 2019 Hu, 2006, IR plus vacuum ultraviolet spectroscopy of neutral and ionic organic acid monomers and clusters: propanoic acid, J. Chem. Phys., 125 Inokuchi, 2003, Infrared photodissociation spectroscopy of protonated formic acid and acetic acid clusters, J. Phys. Chem., 107, 11319, 10.1021/jp030475n Patrick, 2017, Effects of ESI conditions on kinetic trapping of the solution-phase protonation isomer of p-aminobenzoic acid in the gas phase, Int. J. Mass Spectrom., 418, 148, 10.1016/j.ijms.2016.09.022 Yacovitch, 2013, Vibrational spectroscopy of bisulfate/sulfuric acid/water clusters: structure, stability, and infrared multiple-photon dissociation intensities, J. Phys. Chem., 117, 7081, 10.1021/jp400154v Leavitt, 2012, Isomer-specific IR-IR double resonance spectroscopy of D2-tagged protonated dipeptides prepared in a cryogenic ion trap, J. Phys. Chem. Lett., 3, 1099, 10.1021/jz3003074 Wolk, 2014, Cryogenic ion chemistry and spectroscopy, Acc. Chem. Res., 47, 202, 10.1021/ar400125a Yang, 2019, Deconstructing water’s diffuse OH stretching vibrational spectrum with cold clusters, Science, 364, 275, 10.1126/science.aaw4086 Olesen, 2009, Redshift or adduct stabilization-A computational study of hydrogen bonding in adducts of protonated carboxylic acids, Eur. J. Mass Spectrom., 15, 239, 10.1255/ejms.970 Johnson, 2014, Communication: He-tagged vibrational spectra of the SarGlyH+ and H+(H2O)2,3 ions: quantifying tag effects in cryogenic ion vibrational predissociation (CIVP) spectroscopy, J. Chem. Phys., 140, 221101, 10.1063/1.4880475 Ludwig, 2002, The effect of hydrogen bonding on the thermodynamic and spectroscopic properties of molecular clusters and liquids, Phys. Chem. Chem. Phys., 4, 5481, 10.1039/B207000F Albrecht, 2013, Hydrogen bond cooperativity in water hexamers: atomic energy perspective of local stabilities, J. Phys. Chem., 117, 10790, 10.1021/jp407371c Guevara-Vela, 2016, Hydrogen bond cooperativity and anticooperativity within the water hexamer, Phys. Chem. Chem. Phys., 18, 19557, 10.1039/C6CP00763E Olesen, 2011, Tuning the intermolecular proton bond in the H5O2+ ’Zundel ion’ scaffold, Chem. Phys. Lett., 509, 89, 10.1016/j.cplett.2011.04.060 Leavitt, 2013 Craig, 2017, Hidden role of intermolecular proton transfer in the anomalously diffuse vibrational spectrum of a trapped hydronium ion, Proc. Natl. Acad. Sci. U.S.A., 114, E4706, 10.1073/pnas.1705089114 Matthews, 2017, Experiment and theory confirm that UV laser photodissociation spectroscopy can distinguish protomers formed via electrospray, Phys. Chem. Chem. Phys., 17434, 10.1039/C7CP02817B