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[{"id":79724303,"identifier":"Attachment_79724303","shouldShowBulkDownload":false}]; window.loswp.shouldDetectTimezone = true; window.loswp.shouldShowBulkDownload = true; window.loswp.showSignupCaptcha = false window.loswp.willEdgeCache = false; window.loswp.work = {"work":{"id":69747753,"created_at":"2022-01-28T01:24:55.001-08:00","from_world_paper_id":193726923,"updated_at":"2024-11-22T22:43:16.459-08:00","_data":{"publisher":"American Chemical Society (ACS)","grobid_abstract":"Reaction enthalpies and reaction volumes of proton-transfer reactions in aqueous solutions of 3-hydroxypyridine have been estimated by measuring UV-visible absorption spectra at different temperatures, pressures, and pH values. Using these results together with published thermodynamic and kinetic data, we have simulated the relaxation spectrum of the proton-transfer reactions of 3-hydroxypyridine in aqueous solution. The first process identified in our normal mode analysis is the relaxation of the well-known tautomeric equilibrium between the neutral form and the zwitterion, AN = A,. The second relaxation process is the overall reaction A+ + A-= XAN + (2-x)Az, with x being roughly equal to unity. The amplitude of this relaxation is significantly smaller than that of the first. The third relaxation process consists of two branches. The first branch is the overall reaction A+ = XAN + (1x)A2 + H+, x-0.5, at pH \u003c\u003c 7, and the second branch is the overall reaction XAN + (1x)AZ + OH-= A-+ H20, x-0.5, at pH \u003e\u003e 7. The fourth relaxation process is more complicated than the others. It consists mainly of hydrolysis reactions at pH \u003c\u003c 7 and protolysis reactions at pH \u003e\u003e 7.","publication_date":"1989,,","publication_name":"The Journal of Physical Chemistry","grobid_abstract_attachment_id":"79724303"},"document_type":"paper","pre_hit_view_count_baseline":null,"quality":"high","language":"en","title":"Proton-transfer reactions of dibasic acids in aqueous solution: 3-hydroxypyridine and anthranilic acid","broadcastable":true,"draft":null,"has_indexable_attachment":true,"indexable":true}}["work"]; window.loswp.workCoauthors = [11507755]; window.loswp.locale = "en"; window.loswp.countryCode = "SG"; window.loswp.cwvAbTestBucket = ""; window.loswp.designVariant = "ds_vanilla"; window.loswp.fullPageMobileSutdModalVariant = "full_page_mobile_sutd_modal"; window.loswp.useOptimizedScribd4genScript = false; window.loginModal = {}; window.loginModal.appleClientId = 'edu.academia.applesignon';</script><script defer="" src="https://accounts.google.com/gsi/client"></script><div class="ds-loswp-container"><div class="ds-work-card--grid-container"><div class="ds-work-card--container js-loswp-work-card"><div class="ds-work-card--cover"><div class="ds-work-cover--wrapper"><div class="ds-work-cover--container"><button class="ds-work-cover--clickable js-swp-download-button" data-signup-modal="{"location":"swp-splash-paper-cover","attachmentId":79724303,"attachmentType":"pdf"}"><img alt="First page of “Proton-transfer reactions of dibasic acids in aqueous solution: 3-hydroxypyridine and anthranilic acid”" class="ds-work-cover--cover-thumbnail" src="https://0.academia-photos.com/attachment_thumbnails/79724303/mini_magick20220128-5900-nu7krc.png?1643362361" /><img alt="PDF Icon" class="ds-work-cover--file-icon" src="//a.academia-assets.com/images/single_work_splash/adobe_icon.svg" /><div class="ds-work-cover--hover-container"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">download</span><p>Download Free PDF</p></div><div class="ds-work-cover--ribbon-container">Download Free PDF</div><div class="ds-work-cover--ribbon-triangle"></div></button></div></div></div><div class="ds-work-card--work-information"><h1 class="ds-work-card--work-title">Proton-transfer reactions of dibasic acids in aqueous solution: 3-hydroxypyridine and anthranilic acid</h1><div class="ds-work-card--work-authors ds-work-card--detail"><a class="ds-work-card--author js-wsj-grid-card-author ds2-5-body-md ds2-5-body-link" data-author-id="11507755" href="https://independent.academia.edu/PSchuster"><img alt="Profile image of Peter Schuster" class="ds-work-card--author-avatar" src="https://0.academia-photos.com/11507755/5025271/5767664/s65_peter.schuster.jpg" />Peter Schuster</a></div><div class="ds-work-card--detail"><p class="ds-work-card--detail ds2-5-body-sm">1989, The Journal of Physical Chemistry</p><div class="ds-work-card--work-metadata"><div class="ds-work-card--work-metadata__stat"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">visibility</span><p class="ds2-5-body-sm" id="work-metadata-view-count">…</p></div><div class="ds-work-card--work-metadata__stat"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">description</span><p class="ds2-5-body-sm">10 pages</p></div><div class="ds-work-card--work-metadata__stat"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">link</span><p class="ds2-5-body-sm">1 file</p></div></div><script>(async () => { const workId = 69747753; 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if (!viewCountBody) { throw new Error('Failed to find work views element'); } viewCountBody.textContent = `${commaizedViewCount} views`; } catch (error) { // Remove the whole views element if there was some issue parsing. document.getElementById('work-metadata-view-count')?.parentNode?.remove(); throw new Error(`Failed to parse view count: ${viewCount}`, error); } }; // If the DOM is still loading, wait for it to be ready before updating the view count. if (document.readyState === "loading") { document.addEventListener('DOMContentLoaded', () => { updateViewCount(viewCount); }); // Otherwise, just update it immediately. } else { updateViewCount(viewCount); } })();</script></div><p class="ds-work-card--work-abstract ds-work-card--detail ds2-5-body-md">Reaction enthalpies and reaction volumes of proton-transfer reactions in aqueous solutions of 3-hydroxypyridine have been estimated by measuring UV-visible absorption spectra at different temperatures, pressures, and pH values. Using these results together with published thermodynamic and kinetic data, we have simulated the relaxation spectrum of the proton-transfer reactions of 3-hydroxypyridine in aqueous solution. The first process identified in our normal mode analysis is the relaxation of the well-known tautomeric equilibrium between the neutral form and the zwitterion, AN = A,. The second relaxation process is the overall reaction A+ + A-= XAN + (2-x)Az, with x being roughly equal to unity. The amplitude of this relaxation is significantly smaller than that of the first. The third relaxation process consists of two branches. The first branch is the overall reaction A+ = XAN + (1x)A2 + H+, x-0.5, at pH << 7, and the second branch is the overall reaction XAN + (1x)AZ + OH-= A-+ H20, x-0.5, at pH >> 7. The fourth relaxation process is more complicated than the others. It consists mainly of hydrolysis reactions at pH << 7 and protolysis reactions at pH >> 7.</p><div class="ds-work-card--button-container"><button class="ds2-5-button js-swp-download-button" data-signup-modal="{"location":"continue-reading-button--work-card","attachmentId":79724303,"attachmentType":"pdf","workUrl":"https://www.academia.edu/69747753/Proton_transfer_reactions_of_dibasic_acids_in_aqueous_solution_3_hydroxypyridine_and_anthranilic_acid"}">See full PDF</button><button class="ds2-5-button ds2-5-button--secondary js-swp-download-button" data-signup-modal="{"location":"download-pdf-button--work-card","attachmentId":79724303,"attachmentType":"pdf","workUrl":"https://www.academia.edu/69747753/Proton_transfer_reactions_of_dibasic_acids_in_aqueous_solution_3_hydroxypyridine_and_anthranilic_acid"}"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">download</span>Download PDF</button></div></div></div></div><div data-auto_select="false" data-client_id="331998490334-rsn3chp12mbkiqhl6e7lu2q0mlbu0f1b" data-doc_id="79724303" data-landing_url="https://www.academia.edu/69747753/Proton_transfer_reactions_of_dibasic_acids_in_aqueous_solution_3_hydroxypyridine_and_anthranilic_acid" data-login_uri="https://www.academia.edu/registrations/google_one_tap" data-moment_callback="onGoogleOneTapEvent" id="g_id_onload"></div><div class="ds-top-related-works--grid-container"><div class="ds-related-content--container ds-top-related-works--container"><h2 class="ds-related-content--heading">Related papers</h2><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="0" data-entity-id="21480319" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/21480319/A_theoretical_study_of_proton_transfers_in_aqueous_para_ortho_hydroxypyridine_and_para_ortho_hydroxyquinoline">A theoretical study of proton transfers in aqueous para-, ortho-hydroxypyridine and para-, ortho-hydroxyquinoline</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="37423" href="https://dal.academia.edu/RussellBoyd">Russell Boyd</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Chemical Physics Letters, 1996</p><p class="ds-related-work--abstract ds2-5-body-sm">The structures and relative stabilities of the four different forms of hydroxypyridine and hydroxyquinoline (normal, protonated cation, deprotonated anion and zwitterion) in the gas phase have been calculated at the M¢ller-Plesset (MP) perturbation and coupled-cluster theory levels with basis sets up to 6-3 I+G**. The solvation free energies of the reactions were treated with the SMx series of aqueous solvation models by Cramer and Truhlar. By combining the PM3-SM3 model for solvation with the MP2/6-31 +G** level treatment for the gas-phase species, it is found that the free energy changes of the proton transfer reactions can be predicted reasonably well.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"A theoretical study of proton transfers in aqueous para-, ortho-hydroxypyridine and para-, ortho-hydroxyquinoline","attachmentId":41904253,"attachmentType":"pdf","work_url":"https://www.academia.edu/21480319/A_theoretical_study_of_proton_transfers_in_aqueous_para_ortho_hydroxypyridine_and_para_ortho_hydroxyquinoline","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/21480319/A_theoretical_study_of_proton_transfers_in_aqueous_para_ortho_hydroxypyridine_and_para_ortho_hydroxyquinoline"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="1" data-entity-id="69744470" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/69744470/Proton_transfer_reactions_in_aqueous_solutions_of_pyridoxamine_phosphate">Proton transfer reactions in aqueous solutions of pyridoxamine phosphate</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="11507755" href="https://independent.academia.edu/PSchuster">Peter Schuster</a></div><p class="ds-related-work--metadata ds2-5-body-xs">European Biophysics Journal, 1988</p><p class="ds-related-work--abstract ds2-5-body-sm">UV-visible and 13 C NMR measurements described in the literature and our 31p NMR measurements support the following mechanism of proton transfer reactions in aqueous solutions of pyridoxamine phosphate: Only the tautomeric equilibrium between neutral form, AN, and zwitterion, Az, which is analogous to the tautomeric equilibrium of 3-hydroxypyridine in aqueous solution, is important, and that equilibrium does not change upon the dissociation of the second phosphate proton. With these simplifying assumptions, we have simulated the relaxation spectrum of the proton transfer reactions of pyridoxamine phosphate in water using parameters from analogous reactions and compared it with our ultrasound and temperature jump measurements. We have found that the relaxation process measured by the temperature jump experiment is mainly caused by the overall reaction AN = Az (or AN = Az) and the ultrasound absorption at the isoelectric point between pK2 and pK3 is mainly caused by the overall reaction A ++xAN+(1-x)Az=yAN+(2-y)Az, 0_x_l, 0____y=<2.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Proton transfer reactions in aqueous solutions of pyridoxamine phosphate","attachmentId":79722279,"attachmentType":"pdf","work_url":"https://www.academia.edu/69744470/Proton_transfer_reactions_in_aqueous_solutions_of_pyridoxamine_phosphate","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/69744470/Proton_transfer_reactions_in_aqueous_solutions_of_pyridoxamine_phosphate"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="2" data-entity-id="48763014" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/48763014/Parallel_proton_transfer_pathways_in_aqueous_acid_base_reactions">Parallel proton transfer pathways in aqueous acid-base reactions</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="123689565" href="https://independent.academia.edu/BakkerHuib">Huib Bakker</a></div><p class="ds-related-work--metadata ds2-5-body-xs">The Journal of Chemical Physics, 2008</p><p class="ds-related-work--abstract ds2-5-body-sm">We study the mechanism of proton transfer ͑PT͒ between the photoacid 8-hydroxy-1,3, 6-pyrenetrisulfonic acid ͑HPTS͒ and the base chloroacetate in aqueous solution. We investigate both proton and deuteron transfer reactions in solutions with base concentrations ranging from 0.25M to 4M. Using femtosecond midinfrared spectroscopy, we probe the vibrational responses of HPTS, its conjugate photobase, the hydrated proton/deuteron, and chloroacetate. The measurement of these four resonances allows us to follow the sequence of proton departure from the acid, its uptake by the water solvent, and its arrival at the base. In recent studies it was shown that proton transfer to carboxylate bases proceeds via Grotthuss conduction through a water wire connecting the acid and the base ͓Mohammed et al.,</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Parallel proton transfer pathways in aqueous acid-base reactions","attachmentId":67209818,"attachmentType":"pdf","work_url":"https://www.academia.edu/48763014/Parallel_proton_transfer_pathways_in_aqueous_acid_base_reactions","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/48763014/Parallel_proton_transfer_pathways_in_aqueous_acid_base_reactions"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="3" data-entity-id="93486463" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/93486463/Aqueous_bimolecular_proton_transfer_in_acid_base_neutralization">Aqueous bimolecular proton transfer in acid–base neutralization</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="141536475" href="https://independent.academia.edu/OmarMohammed124">Omar Mohammed</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Chemical Physics, 2007</p><p class="ds-related-work--abstract ds2-5-body-sm">We report on a comparative femtosecond infrared study of the bimolecular proton transfer reaction dynamics of the photoacid pyranine (8-hydroxy-1,3,6-trisulfonate-pyrene, abbreviated as HPTS) with the family of carboxylate bases À OOCCH (3Àx) Cl x (x = 0-3) in aqueous solution. We use a generalized reaction model consisting of n proton transfer reaction pathways between photoacid and base, each pathway characterized by the number n of water molecules functioning as solvent switch facilitating an efficient transfer. The dynamics of the different proton transfer pathways have been followed by inspection of appropriate vibrational modes marking the progress of the reaction, and allow the direct observation of the transient relay mechanism of proton through one bridging water molecule in a loose photoacid-base configuration of the type HPTS À Á Á ÁH 3 O + Á Á Á À OOCCH (3Àx) Cl x (x = 0-3). By applying a global fit procedure on the n-coupled reaction pathways, with full reversibility and detailed balance, we find for the reaction series that the encounter complex formed after mutual diffusion between photoacid and base, and subsequent desolvation, follows in general the loose complex pathway with one water molecule bridging acid and base. Only for the weakest base studied, trichloroacetate, larger solvent switches with n P 2 water molecules are important in the transfer dynamics. Whereas transfer in the tight complex with no water spacer (n = 0) occurs within time resolution of 150 fs, the transfer in the loose (n = 1) complex proceeds in a sequential fashion where the first transfer occurs within time resolution, irrespective of base strength, whereas the second transfer from the water to the base is activated and conforms to a correlation between free energy and reaction rate.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Aqueous bimolecular proton transfer in acid–base neutralization","attachmentId":96211511,"attachmentType":"pdf","work_url":"https://www.academia.edu/93486463/Aqueous_bimolecular_proton_transfer_in_acid_base_neutralization","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/93486463/Aqueous_bimolecular_proton_transfer_in_acid_base_neutralization"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="4" data-entity-id="90970706" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/90970706/Proton_Transfer_Reaction_Dynamics_of_Pyranine_in_DMSO_Water_Mixtures">Proton Transfer Reaction Dynamics of Pyranine in DMSO/Water Mixtures</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="245830467" href="https://independent.academia.edu/ankurawasthi20">ankur awasthi</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Chemphyschem : a European journal of chemical physics and physical chemistry, 2018</p><p class="ds-related-work--abstract ds2-5-body-sm">Photoinduced intermolecular excited-state proton transfer (ESPT) reactions are ubiquitous in chemistry and biology. ESPT reactions are extremely sensitive to the nature of water molecules in its microenvironment and thus serve as a sensitive reporter for the water structure and dynamics in a system. Herein, the photoinduced intermolecular ESPT reaction of 8-hydroxypyrene-1,3,5-trisulfonic acid (HPTS, also known as pyranine) has been investigated in various DMSO/water mixtures by using steady-state and time-resolved emission spectroscopy. The DMSO/water binary mixture yields an interesting and anomalous behavior for the proton transfer reaction dynamics of HPTS at a mole fraction of DMSO (X) of 0.41-0.51, which has also been previously investigated and projected as an anomalous region by molecular dynamics simulation and other experimental techniques. The extreme slowdown of the proton transfer reaction observed at X=0.41-0.51 has been attributed to the slow solvation dynamics, as we...</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Proton Transfer Reaction Dynamics of Pyranine in DMSO/Water Mixtures","attachmentId":94387823,"attachmentType":"pdf","work_url":"https://www.academia.edu/90970706/Proton_Transfer_Reaction_Dynamics_of_Pyranine_in_DMSO_Water_Mixtures","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/90970706/Proton_Transfer_Reaction_Dynamics_of_Pyranine_in_DMSO_Water_Mixtures"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="5" data-entity-id="16197133" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/16197133/Protonation_of_Excited_State_Pyrene_1_Carboxylate_by_Phosphate_and_Organic_Acids_in_Aqueous_Solution_Studied_by_Fluorescence_Spectroscopy">Protonation of Excited State Pyrene-1-Carboxylate by Phosphate and Organic Acids in Aqueous Solution Studied by Fluorescence Spectroscopy</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="35305422" href="https://independent.academia.edu/JaneVanderkooi">Jane Vanderkooi</a><span>, </span><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="35345666" href="https://independent.academia.edu/BogumilZelent">Bogumil Zelent</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Biophysical Journal, 2006</p><p class="ds-related-work--abstract ds2-5-body-sm">Pyrene-1-carboxylic acid has a pK of 4.0 in the ground state and 8.1 in the singlet electronic excited state. In the pH range of physiological interest (pH ;5-8), the ground state compound is largely ionized as pyrene-1-carboxylate, but protonation of the excited state molecule occurs when a proton donor reacts with the carboxylate during the excited state lifetime of the fluorophore. Both forms of the pyrene derivatives are fluorescent, and in this work the protonation reaction was measured by monitoring steady-state and time-resolved fluorescence. The rate of protonation of pyrene-COO ÿ by acetic, chloroacetic, lactic, and cacodylic acids is a function of DpK, as predicted by Marcus theory. The rate of proton transfer from these acids saturates at high concentration, as expected for the existence of an encounter complex. Trihydrogen-phosphate is a much better proton donor than dihydrogen-and monohydrogen-phosphate, as can be seen by the pH dependence. The proton-donating ability of phosphate does not saturate at high concentrations, but increases with increasing phosphate concentration. We suggest that enhanced rate of proton transfer at high phosphate concentrations may be due to the dual proton donating and accepting nature of phosphate, in analogy to the Grotthuss mechanism for proton transfer in water. It is suggested that in molecular structures containing multiple phosphates, such as membrane surfaces and DNA, proton transfer rates will be enhanced by this mechanism.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Protonation of Excited State Pyrene-1-Carboxylate by Phosphate and Organic Acids in Aqueous Solution Studied by Fluorescence Spectroscopy","attachmentId":42641069,"attachmentType":"pdf","work_url":"https://www.academia.edu/16197133/Protonation_of_Excited_State_Pyrene_1_Carboxylate_by_Phosphate_and_Organic_Acids_in_Aqueous_Solution_Studied_by_Fluorescence_Spectroscopy","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/16197133/Protonation_of_Excited_State_Pyrene_1_Carboxylate_by_Phosphate_and_Organic_Acids_in_Aqueous_Solution_Studied_by_Fluorescence_Spectroscopy"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="6" data-entity-id="121539242" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/121539242/Investigations_into_an_Intramolecular_Proton_Transfer_and_Solvent_Dependent_Acid_Base_Equilibria_in_2_6_Pyridine_Diacetic_Acid">Investigations into an Intramolecular Proton Transfer and Solvent Dependent Acid‐Base Equilibria in 2,6‐Pyridine Diacetic Acid</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="311839246" href="https://independent.academia.edu/VarmaRambaran">Varma Rambaran</a></div><p class="ds-related-work--metadata ds2-5-body-xs">ChemistrySelect, 2019</p><p class="ds-related-work--abstract ds2-5-body-sm">This study highlights an intramolecular proton transfer and solvent dependent acid‐base equilibria in 2,6‐pyridine diacetic acid, as contributing factors to a solid state reversible structural transformation and a spontaneous double decarboxylation. Differential scanning calorimetry exhibited several reversible phase transitions, with the most pronounced change occurring at 168 K. A reversible structural transformation, from the monoclinic system to the triclinic one, was confirmed via temperature dependent X‐ray diffraction studies. In water, absorbance shifts from 198 to 210 nm were observed, correlating to the deprotonation of the carboxylic groups, synergistically, protonation of the pyridine ring showed shifts from 280 to 270 nm. 1H NMR provided evidence of the solvent dependent, irreversible conversion to 2,6‐dimethylpyridine via sequential decarboxylations. The ΔS≠ for each decarboxylation were 39.53 ± 3.87 and 23.56 ± 2.84 JK−1mol−1 respectively. Finally, the rate constants ...</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Investigations into an Intramolecular Proton Transfer and Solvent Dependent Acid‐Base Equilibria in 2,6‐Pyridine Diacetic Acid","attachmentId":116388153,"attachmentType":"pdf","work_url":"https://www.academia.edu/121539242/Investigations_into_an_Intramolecular_Proton_Transfer_and_Solvent_Dependent_Acid_Base_Equilibria_in_2_6_Pyridine_Diacetic_Acid","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/121539242/Investigations_into_an_Intramolecular_Proton_Transfer_and_Solvent_Dependent_Acid_Base_Equilibria_in_2_6_Pyridine_Diacetic_Acid"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="7" data-entity-id="60660249" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/60660249/Proton_Transfer_from_a_Photoacid_to_Water_First_Principles_Simulations_and_Fast_Fluorescence_Spectroscopy">Proton Transfer from a Photoacid to Water: First Principles Simulations and Fast Fluorescence Spectroscopy</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="15986729" href="https://stanford.academia.edu/ToddMartinez">Todd Martinez</a></div><p class="ds-related-work--abstract ds2-5-body-sm">Proton transfer reactions are ubiquitous in chemistry, especially in aqueous solutions. We investigate photo-induced proton transfer between the photoacid 8-hydroxypyrene-1,3,6- trisulfonate (HPTS) and water using fast fluorescence spectroscopy and ab initio molecular dynamics simulations. Photo-excitation causes rapid proton release from the HPTS hydroxyl. Previous experiments on HPTS/water described the progress from photoexcitation to proton diffusion using kinetic equations with two time constants. The shortest time constant has been interpreted as protonated and photoexcited HPTS evolving into an “associated” state, where the proton is “shared” between the HPTS hydroxyl and an originally hydrogen bonded water. The longer time constant has been interpreted as indicating evolution to a “solvent separated” state where the shared proton undergoes long distance diffusion. In this work, we refine the previous experimental results using very pure HPTS. We then use excited state ab ini...</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Proton Transfer from a Photoacid to Water: First Principles Simulations and Fast Fluorescence Spectroscopy","attachmentId":74003466,"attachmentType":"pdf","work_url":"https://www.academia.edu/60660249/Proton_Transfer_from_a_Photoacid_to_Water_First_Principles_Simulations_and_Fast_Fluorescence_Spectroscopy","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/60660249/Proton_Transfer_from_a_Photoacid_to_Water_First_Principles_Simulations_and_Fast_Fluorescence_Spectroscopy"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="8" data-entity-id="41267655" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/41267655/Coherent_intermolecular_proton_transfer_in_acid_base_reaction_of_excited_state_pyranine">Coherent intermolecular proton transfer in acid-base reaction of excited state pyranine</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="128515786" href="https://bdsongonline.academia.edu/DrNizamUddin">Dr. Nizam Uddin</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Royal Society of Chemistry</p><p class="ds-related-work--abstract ds2-5-body-sm">Detailed molecular dynamics of an acid-base reaction has been the subject of extensive investigations. Here we report excited state proton transfer dynamics of pyranine (8-hydroxypyrene-1{,}3{,}6-trisulfonic acid{,} HPTS) in acetate buffer by time-resolved fluorescence (TF) and quantum mechanical/effective fragment potential molecular dynamics (QM/EFP-MD) simulation. High time resolution in TF and TF spectra measurements allow acquisition of accurate reaction kinetics. Upon photoexcitation of HPTS{,} the proton (deuterium) is transferred coherently to acetate in 60 fs (80 fs) for a contact pair of HPTS (DPTS) and acetate by hydrogen bond{,} which comprises approximately 28 % of the population. ESPT proceeds slowly in picosecond time scale for the remaining HPTS as reported previously. Coherent wave packet motions of the reactant (acid) and the product (conjugate base) enable acquisition of the vibrational spectra of excited states via TF (VETF). Comparison of the VETFs of the reactant and product and calculation of the Huang-Rhys factors (vibrational reorganization energies) identify the vibrational modes that actively participate the coherent proton transfer. In particular{,} the 246 cm-1 vibrational mode{,} which consists of in-plane skeletal stretching motion{,} promotes the ESPT by transferring the donor oxygen towards the acceptor oxygen in acetate. QM/EFP MD simulation corroborates the experiment and provides molecular details of the ESPT.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Coherent intermolecular proton transfer in acid-base reaction of excited state pyranine","attachmentId":61486898,"attachmentType":"pdf","work_url":"https://www.academia.edu/41267655/Coherent_intermolecular_proton_transfer_in_acid_base_reaction_of_excited_state_pyranine","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/41267655/Coherent_intermolecular_proton_transfer_in_acid_base_reaction_of_excited_state_pyranine"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="9" data-entity-id="13485740" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/13485740/Computational_Study_of_Proton_Transfer_in_Tautomers_of_3_and_5_Hydroxypyrazole_Assisted_by_Water">Computational Study of Proton Transfer in Tautomers of 3- and 5-Hydroxypyrazole Assisted by Water</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="32697110" href="https://ucd.academia.edu/GoarSanchezsanz">Goar Sanchez-sanz</a></div><p class="ds-related-work--metadata ds2-5-body-xs">ChemPhysChem, 2015</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Computational Study of Proton Transfer in Tautomers of 3- and 5-Hydroxypyrazole Assisted by Water","attachmentId":45285469,"attachmentType":"pdf","work_url":"https://www.academia.edu/13485740/Computational_Study_of_Proton_Transfer_in_Tautomers_of_3_and_5_Hydroxypyrazole_Assisted_by_Water","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/13485740/Computational_Study_of_Proton_Transfer_in_Tautomers_of_3_and_5_Hydroxypyrazole_Assisted_by_Water"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div></div></div><div class="ds-sticky-ctas--wrapper js-loswp-sticky-ctas hidden"><div class="ds-sticky-ctas--grid-container"><div class="ds-sticky-ctas--container"><button class="ds2-5-button js-swp-download-button" data-signup-modal="{"location":"continue-reading-button--sticky-ctas","attachmentId":79724303,"attachmentType":"pdf","workUrl":null}">See full PDF</button><button class="ds2-5-button ds2-5-button--secondary js-swp-download-button" data-signup-modal="{"location":"download-pdf-button--sticky-ctas","attachmentId":79724303,"attachmentType":"pdf","workUrl":null}"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">download</span>Download PDF</button></div></div></div><div class="ds-below-fold--grid-container"><div class="ds-work--container js-loswp-embedded-document"><div class="attachment_preview" data-attachment="Attachment_79724303" style="display: none"><div class="js-scribd-document-container"><div class="scribd--document-loading js-scribd-document-loader" style="display: block;"><img alt="Loading..." src="//a.academia-assets.com/images/loaders/paper-load.gif" /><p>Loading Preview</p></div></div><div style="text-align: center;"><div class="scribd--no-preview-alert js-preview-unavailable"><p>Sorry, preview is currently unavailable. You can download the paper by clicking the button above.</p></div></div></div></div><div class="ds-sidebar--container js-work-sidebar"><div class="ds-related-content--container"><h2 class="ds-related-content--heading">Related papers</h2><div class="ds-related-work--container js-related-work-sidebar-card" data-collection-position="0" data-entity-id="50132398" data-sort-order="default"><a class="ds-related-work--title js-related-work-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/50132398/Computational_study_of_the_intramolecular_proton_transfer_reactions_of_dipicolinic_acid_pyridine_2_6_dicarboxylic_acid_and_its_dimers">Computational study of the intramolecular proton transfer reactions of dipicolinic acid (pyridine-2,6-dicarboxylic acid) and its dimers</a><div class="ds-related-work--metadata"><a class="js-related-work-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="59570523" href="https://independent.academia.edu/MohammadIzadyar">Mohammad Izadyar</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Computational and Theoretical Chemistry, 2013</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Computational study of the intramolecular proton transfer reactions of dipicolinic acid (pyridine-2,6-dicarboxylic acid) and its dimers","attachmentId":68232568,"attachmentType":"pdf","work_url":"https://www.academia.edu/50132398/Computational_study_of_the_intramolecular_proton_transfer_reactions_of_dipicolinic_acid_pyridine_2_6_dicarboxylic_acid_and_its_dimers","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" href="https://www.academia.edu/50132398/Computational_study_of_the_intramolecular_proton_transfer_reactions_of_dipicolinic_acid_pyridine_2_6_dicarboxylic_acid_and_its_dimers"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-related-work-sidebar-card" data-collection-position="1" data-entity-id="66161226" data-sort-order="default"><a class="ds-related-work--title js-related-work-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/66161226/Spectroscopic_investigation_on_proton_transfer_reaction_in_the_complex_of_2_aminopyridine_with_2_6_dichloro_4_nitrophenol_in_different_solvents">Spectroscopic investigation on proton transfer reaction in the complex of 2-aminopyridine with 2, 6-dichloro-4-nitrophenol in different solvents</a><div class="ds-related-work--metadata"><a class="js-related-work-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="207186848" href="https://independent.academia.edu/KhairiaAlAhmary">Khairia Al-Ahmary</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Journal of Molecular Liquids, 2011</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Spectroscopic investigation on proton transfer reaction in the complex of 2-aminopyridine with 2, 6-dichloro-4-nitrophenol in different solvents","attachmentId":77463066,"attachmentType":"pdf","work_url":"https://www.academia.edu/66161226/Spectroscopic_investigation_on_proton_transfer_reaction_in_the_complex_of_2_aminopyridine_with_2_6_dichloro_4_nitrophenol_in_different_solvents","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span 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class="ds-related-work--metadata"><a class="js-related-work-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="212827999" href="https://independent.academia.edu/TRANTHIThuHoa">Thu-Hoa TRAN-THI</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Chemical Physics Letters, 2000</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Primary ultrafast events preceding the photoinduced proton transfer from pyranine to water","attachmentId":98356973,"attachmentType":"pdf","work_url":"https://www.academia.edu/96466139/Primary_ultrafast_events_preceding_the_photoinduced_proton_transfer_from_pyranine_to_water","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link 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