{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,25]],"date-time":"2025-10-25T12:38:14Z","timestamp":1761395894049,"version":"build-2065373602"},"reference-count":116,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2020,11,23]],"date-time":"2020-11-23T00:00:00Z","timestamp":1606089600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["18-13-00050"],"award-info":[{"award-number":["18-13-00050"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Polish Government Plenipotentiary for JINR in Dubna","award":["75\/24\/2020"],"award-info":[{"award-number":["75\/24\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>Experimental and theoretical results are presented based on vibrational spectra and motional dynamics of 1,8-bis(dimethylamino)naphthalene (DMAN) and its protonated forms (DMANH+ and the DMANH+ HSO4\u2212 complex). The studies of these compounds have been performed in the gas phase and solid-state. Spectroscopic investigations were carried out by infrared spectroscopy (IR), Raman, and incoherent inelastic neutron scattering (IINS) experimental methods. Density functional theory (DFT) and Car\u2013Parrinello molecular dynamics (CPMD) methods were applied to support our experimental findings. The fundamental investigations of hydrogen bridge vibrations were accomplished on the basis of isotopic substitutions (NH \u2192 ND). Special attention was paid to the bridged proton dynamics in the DMANH+ complex, which was found to be affected by interactions with the HSO4\u2212 anion.<\/jats:p>","DOI":"10.3390\/sym12111924","type":"journal-article","created":{"date-parts":[[2020,11,23]],"date-time":"2020-11-23T11:50:34Z","timestamp":1606132234000},"page":"1924","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Symmetry\/Asymmetry of the NHN Hydrogen Bond in Protonated 1,8-Bis(dimethylamino)naphthalene"],"prefix":"10.3390","volume":"12","author":[{"given":"Patrycja","family":"Pi\u0119ko\u015b","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, 14 F. Joliot-Curie str., 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6601-9124","authenticated-orcid":false,"given":"Aneta","family":"Jezierska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, 14 F. Joliot-Curie str., 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2952-9739","authenticated-orcid":false,"given":"Jaros\u0142aw J.","family":"Panek","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, 14 F. Joliot-Curie str., 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eugene A.","family":"Goremychkin","sequence":"additional","affiliation":[{"name":"Frank Laboratory of Neutron Physics, Joint Institute for Nuclear Research 6 F. Joliot-Curie str., 141980 Dubna, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander F.","family":"Pozharskii","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Southern Federal University, Zorge 7, 344090 Rostov-on-Don, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7047-789X","authenticated-orcid":false,"given":"Alexander S.","family":"Antonov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, St. Petersburg State University, Universitetskij pr. 26, 198504 St. Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8426-3988","authenticated-orcid":false,"given":"Peter M.","family":"Tolstoy","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, St. Petersburg State University, Universitetskij pr. 26, 198504 St. Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1013-4945","authenticated-orcid":false,"given":"Aleksander","family":"Filarowski","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, 14 F. 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Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1016\/0166-1280(90)80093-4","article-title":"Ab initio SCF and M\u00f8ller-Plesset calculations on the hydrogen bond in hydrogen malonate: Effects of neighbour ions and polarizable medium","volume":"209","author":"Mavri","year":"1990","journal-title":"J. Mol. Struct."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/S0166-1280(98)00075-X","article-title":"Influence of solvation on the hydrogen bond in hydrogen malonate an ab initio and semiempirical study","volume":"432","author":"Mavri","year":"1998","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1884","DOI":"10.1002\/anie.199718841","article-title":"1,8-Bis(dimethylamino)4,5-dihydroxynaphthalene, a Natural, Intramolecularly Protonated \u201cProton Sponge\u201d with Zwitterionic Structure","volume":"36","author":"Staab","year":"1997","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"8559","DOI":"10.1021\/ja00048a031","article-title":"Symmetries of hydrogen bonds in monoanions of dicarboxylic acids","volume":"114","author":"Perrin","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"12641","DOI":"10.1021\/ja9825579","article-title":"Symmetry of the Hydrogen Bond in Malonaldehyde Enol in Solution","volume":"120","author":"Perrin","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"9828","DOI":"10.1021\/jp201073j","article-title":"NMR Study of Conformational Exchange and Geometries of Intramolecular Hydrogen Bonds in Monoanions of Succinic Acid and Derivatives","volume":"115","author":"Guo","year":"2011","journal-title":"J. Phys. Chem. A"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"11180","DOI":"10.1021\/jp304943h","article-title":"Hydrogen Bond Geometries and Proton Tautomerism of Homo-Conjugated Anions of Carboxylic Acids Studied via H\/D Isotope Effects on 13C NMR Chemical Shifts","volume":"116","author":"Guo","year":"2012","journal-title":"J. Phys. Chem. A"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1002\/poc.1219","article-title":"Primary 1 H\/2 H isotope effect in the NMR chemical shift of HClO4 salts of 1,8-bis(dimethylamino)naphthalene derivatives","volume":"20","author":"Chmielewski","year":"2007","journal-title":"J. Phys. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4884","DOI":"10.1039\/C9CP06840F","article-title":"Symmetry and 1 H NMR chemical shifts of short hydrogen bonds: Impact of electronic and nuclear quantum effects","volume":"22","author":"Zhou","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"11581","DOI":"10.1021\/acs.jpcb.5b06171","article-title":"15N and 1 H Solid-State NMR Investigation of a Canonical Low-Barrier Hydrogen-Bond Compound: 1,8-Bis(dimethylamino)naphthalene","volume":"119","author":"White","year":"2015","journal-title":"J. Phys. Chem. B"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6520","DOI":"10.1021\/ja0036965","article-title":"Symmetry of N\u2013H\u2013N Hydrogen Bonds in 1,8-Bis(dimethylamino)naphthalene\u00b7H+ and 2,7-Dimethoxy-1,8-bis(dimethylamino)naphthalene\u00b7H+","volume":"123","author":"Perrin","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1107\/S0108768196003023","article-title":"Neutron Diffraction of a Complex of 1,8-Bis(dimethylamino)naphthalene with 1,2-Dichloromaleic Acid","volume":"52","author":"Wilson","year":"1996","journal-title":"Acta Cryst. B"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2123","DOI":"10.1021\/acs.cgd.5b01788","article-title":"The Effect of Local Crystalline Environment on Hydrogen Atom Behavior in Molecular Complexes of a Proton Sponge","volume":"16","author":"Jones","year":"2016","journal-title":"Cryst. Growth Des."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1039\/C8CP05183F","article-title":"14N NQR spectroscopy reveals the proton position in N\u2013H N bonds: A case study with proton sponges","volume":"21","author":"Gregorovic","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1016\/j.fuel.2018.02.094","article-title":"Proton sponge as a new efficient catalyst for carbon dioxide transformation to methanol: Theoretical approach","volume":"221","author":"Izadyar","year":"2018","journal-title":"Fuel"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1016\/S1386-1425(97)00237-0","article-title":"Incoherent inelastic neutron scattering, Raman and IR absorption studies on 1,8-bis(dimethylamino)naphthalene and its protonated forms","volume":"54","author":"Natkaniec","year":"1998","journal-title":"Spectrochim. Acta A"},{"key":"ref_20","first-page":"101","article-title":"Structure and IR spectra of protonated 1,8-bis(dimethylamino)naphthalene proton sponge","volume":"65","author":"Grech","year":"1992","journal-title":"Croat. Chem. Acta"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"382","DOI":"10.1016\/j.apradiso.2016.10.006","article-title":"Successful application of a neutral organic base, 1,8-bis(tetramethylguanidino)naphthalene (TMGN), for the radiosynthesis of [11C]raclopride","volume":"118","author":"Lee","year":"2016","journal-title":"Appl. Rad. Isotop."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"414","DOI":"10.1002\/bbpc.19981020320","article-title":"Localization of Hydrogen Bond Deuterons in Proton Sponges by Dipolar Solid State N-15 NMR Spectroscopy","volume":"102","author":"Lopez","year":"1998","journal-title":"Ber. Bunsenges. Phys. Chem. Chem. Phys."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1679","DOI":"10.1002\/chem.200902259","article-title":"Symmetrization of Cationic Hydrogen Bridges of Protonated Sponges Induced by Solvent and Counteranion Interactions as Revealed by NMR Spectroscopy","volume":"16","author":"Pietrzak","year":"2010","journal-title":"Chem. Eur. J."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4338","DOI":"10.1021\/ja005890x","article-title":"13C Detected Scalar Nitrogen-Nitrogen Couplings Across the Intramolecular Symmetric NHN Hydrogen Bond of Proton Sponge","volume":"123","author":"Pietrzak","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","first-page":"523","article-title":"X-ray diffraction and solid state NMR studies of 1,8-bis(dimethylamino)naphthalene and its complexes with picric and hexafluorophosphoric acids","volume":"20","author":"Lopez","year":"1996","journal-title":"New J. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"8070","DOI":"10.1021\/ja00466a060","article-title":"NMR isotope shifts as a probe of electronic structure","volume":"99","author":"Saunders","year":"1977","journal-title":"J. Am. Chem. Soc."},{"doi-asserted-by":"crossref","unstructured":"Alder, R.W., Bowman, P.S., Steele, W.R.S., and Winterman, D.R. (1968). The remarkable basicity of 1,8-bis(dimethylamino)naphthalene. J. Chem. Soc. Chem. Commun., 723\u2013724.","key":"ref_27","DOI":"10.1039\/c19680000723"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.1021\/cr940246k","article-title":"In\/Out Isomerism","volume":"96","author":"Alder","year":"1996","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1002\/anie.198808653","article-title":"\u201cProton Sponges\u201d and the Geometry of Hydrogen Bonds: Aromatic Nitrogen Bases with Exceptional Basicities","volume":"27","author":"Staab","year":"1988","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1070\/RC1998v067n01ABEH000377","article-title":"Naphthalene \u201cProton Sponges\u201d","volume":"67","author":"Pozharskii","year":"1998","journal-title":"Russ. Chem. Rev."},{"doi-asserted-by":"crossref","unstructured":"Rappoport, Z. (2007). Proton sponges. The Chemistry of Anilines, J. Wiley & Sons.","key":"ref_31","DOI":"10.1002\/9780470871737"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/j.molstruc.2009.11.057","article-title":"The specificity of the [NHN]+ hydrogen bonds in protonated naphthalene proton sponges","volume":"972","author":"Sobczyk","year":"2010","journal-title":"J. Mol. Struct."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1016\/0022-2860(94)08367-3","article-title":"Proton sponges","volume":"328","author":"Elguero","year":"1994","journal-title":"J. Mol. Struct."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2591","DOI":"10.1021\/acs.jpca.6b01552","article-title":"Experimental Basicities of Phosphazene, Guanidinophosphazene, and Proton Sponge Superbases in the Gas Phase and Solution","volume":"120","author":"Kaljurand","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"7670","DOI":"10.1002\/chem.201402226","article-title":"Superbasic Alkyl-Substituted Bisphosphazene Proton Sponges: Synthesis, Structural Features, Thermodynamic and Kinetic Basicity, Nucleophilicity and Coordination Chemistry","volume":"20","author":"Xie","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1603","DOI":"10.1023\/A:1013868406075","article-title":"Concept of Superbasicity of 1,8-Bis(dialkylamino)naphthalenes ([Proton Sponges])","volume":"37","author":"Korzhenevskaya","year":"2001","journal-title":"Rus. J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1682","DOI":"10.1002\/1521-3765(20020402)8:7<1682::AID-CHEM1682>3.0.CO;2-R","article-title":"1,8-Bis(tetramethylguanidino)naphthalene (TMGN): A New, Superbasic and Kinetically Active \u201cProton Sponge\u201d","volume":"8","author":"Raab","year":"2002","journal-title":"Chem. Eur. J."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"8239\u22128244","DOI":"10.1021\/ja00494a035","article-title":"Base-catalyzed proton transfer from an intramolecularly hydrogen-bonded naphthylammonium ion in 70% dimethyl sulfoxide-water (v\/v)","volume":"100","author":"Hibbert","year":"1978","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1039\/P29870000243","article-title":"Acid\u2013base properties of highly substituted diaminonaphthalenes","volume":"2","author":"Hibbert","year":"1987","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"11420","DOI":"10.1021\/jp9537320","article-title":"ESCA and Solid-State NMR Studies of Ionic Complexes of 1,8- Bis(dimethylamino)naphthalene","volume":"100","author":"He","year":"1996","journal-title":"J. Phys. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1393","DOI":"10.1021\/cg0606848","article-title":"From Proton Disorder to Proton Migration: A Continuum in the Hydrogen Bond of a Proton Sponge in the Solid State","volume":"7","author":"Parkin","year":"2007","journal-title":"Cryst. Grow. Des."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5092","DOI":"10.1021\/cg1007445","article-title":"Charge Densities of Two Polymorphs of Hydrated 1,8-Bis(dimethylamino)naphthalene Hydrochloride; Similarities and Differences","volume":"10","author":"Hoser","year":"2010","journal-title":"Cryst. Grow. Des."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"4259","DOI":"10.1021\/ja029389b","article-title":"From Weak Interactions to Covalent Bonds: A Continuum in the Complexes of 1,8-Bis(dimethylamino)naphthalene","volume":"125","author":"Mallinson","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/0022-2860(90)80501-A","article-title":"Crystallographic Studies on Sterically Affected Chemical-Species 0.2. Molecular and Crystal-Structure of 1,8-Bis(Dimethylamino)-Naphthalene Tetrafluoroborate\u2014Analysis of Distortion of Geometry in the Aromatic Part Due to Intramolecular Hydrogen-Bonding","volume":"240","author":"Krygowski","year":"1990","journal-title":"J. Mol. Struct."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/S0022-2860(02)00216-8","article-title":"Deuterium isotope effects on 15N, 13C and 1 H chemical shifts of proton sponges","volume":"615","author":"Grech","year":"2002","journal-title":"J. Mol. Struct."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1016\/0166-1280(89)85079-1","article-title":"The strange behaviour of the hydrogen bond complexes of 1,8-bis(dimethylamino) naphthalene in solution","volume":"200","year":"1989","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1637","DOI":"10.1021\/jp040618l","article-title":"[NHN]+ Hydrogen Bonding in Protonated 1,8-Bis(dimethylamino)-2,7-dimethoxynaphthalene. X-ray Diffraction, Infrared, and Theoretical ab Initio and DFT Studies","volume":"109","author":"Ozeryanskii","year":"2005","journal-title":"J. Phys. Chem. A"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0022-2860(01)00887-0","article-title":"X-ray diffraction and IR-spectroscopic studies on protonated 4-amino-1,8-bis(dimethyloamino)naphthalene","volume":"607","author":"Ozeryanskii","year":"2002","journal-title":"J. Mol. Struct."},{"key":"ref_49","first-page":"149","article-title":"Proton transfer reactions from N-H acid to proton sponges in acetonitrile. Part 2","volume":"377","author":"Brzezinski","year":"1996","journal-title":"J. Mol. Struct."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1801","DOI":"10.1016\/S1386-1425(00)00239-0","article-title":"Vibrational spectra of the adduct of 1,8-bis(dimethylamino)naphthalene with dichloromaleic acid (DMAN*DCM)","volume":"56","author":"Baran","year":"2000","journal-title":"Spectrochim. Acta A"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1021\/acs.joc.5b01743","article-title":"Synthesis, Theoretical Analysis, and Experimental pKa Determination of a Fluorescent, Nonsymmetric, In\u2212Out Proton Sponge","volume":"81","author":"Belding","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2940","DOI":"10.3762\/bjoc.14.273","article-title":"1,8-Bis(dimethylamino)naphthyl-2-ketimines: Inside vs outside protonation","volume":"14","author":"Antonov","year":"2018","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2360","DOI":"10.1039\/c3ob41986j","article-title":"Out-Basicity of 1,8-bis(dimethylamino)naphthalene: The experimental and theoretical challenge","volume":"12","author":"Ozeryanskii","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3006","DOI":"10.1021\/jo062667v","article-title":"2-\u03b1-hydroxyalkyl- and 2,7-di(\u03b1-hydroxyalkyl)-1,8-bis(dimethylamino)naphthalenes: Stabilization of nonconventional in\/out conformers of \u201cproton sponges\u201d via N\u00b7\u00b7\u00b7H-O intramolecular hydrogen bonding. A remarkable kind of tandem nitrogen inversion","volume":"72","author":"Pozharskii","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1032","DOI":"10.1002\/chem.201302959","article-title":"Synthesis and Theoretical Investigation of a 1,8-Bis(bis(diisopropylamino)cyclopropeniminyl)naphthalene Proton Sponge Derivative","volume":"20","author":"Belding","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1007\/s00894-020-4296-9","article-title":"Theoretical study of intramolecular hydrogen bond in selected symmetric \u201cproton sponges\u201d on the basis of DFT and CPMD methods","volume":"26","author":"Jezierska","year":"2020","journal-title":"J. Mol. Model."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1148","DOI":"10.1021\/ci500560g","article-title":"\u201cZwitterionic proton sponge\u201d hydrogen bonding investigations on the basis of Car-Parrinello molecular dynamics","volume":"55","author":"Jezierska","year":"2015","journal-title":"J. Chem. Inf. Model."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"10576","DOI":"10.1021\/jp4061297","article-title":"Effects of Counterion and Solvent on Proton Location and Proton Transfer Dynamics of N\u2212H\u00b7\u00b7\u00b7N Hydrogen Bond of Monoprotonated 1,8-Bis(dimethylamino)naphthalene","volume":"117","author":"Masuda","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1039\/b814798a","article-title":"Proton transfer in the intramolecular NHN+ bonds in proton sponges with different hydrogen bridge flexibility","volume":"11","author":"Majerz","year":"2009","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3043","DOI":"10.1039\/b717815h","article-title":"The shape of the potential energy curves for NHN+ hydrogen bonds and the influence of non-linearity","volume":"10","author":"Majerz","year":"2008","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1118","DOI":"10.1002\/cphc.201000721","article-title":"Hydrogen Motion in Proton Sponge Cations: A Theoretical Study","volume":"12","author":"Horbatenko","year":"2011","journal-title":"ChemPhysChem"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"10109","DOI":"10.1021\/jo035350t","article-title":"Organometallic Synthesis, Molecular Structure, and Coloration of 2,7-Disubstituted 1,8-Bis(dimethylamino)naphthalenes. How Significant Is the Influence of \u201cButtressing Effect\u201d on Their Basicity?","volume":"68","author":"Pozharskii","year":"2003","journal-title":"J. Org. Chem."},{"doi-asserted-by":"crossref","unstructured":"Alder, R.W., Orpen, A.G., and Sessions, R.B. (1983). The structure of 1,6-diazabicyclo[4.4.4]tetradecane and of its inside protonated ion. J. Chem. Soc. Chem. Commun., 999\u20131000.","key":"ref_63","DOI":"10.1039\/c39830000999"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2840","DOI":"10.1039\/P19810002840","article-title":"Preparation of a range of NNN\u2032N\u2032-tetrasubstituted 1,8-diaminonaphthalenes","volume":"1","author":"Alder","year":"1981","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"6209","DOI":"10.1016\/j.tet.2008.05.001","article-title":"2,7-disubstituted proton sponges as borderline systems for investigating barrier-free intramolecular hydrogen bonds. Protonated 2,7-bis(trimethylsilyl)- and 2,7-di(hydroxymethyl)-1,8-bis(dimethylamino)naphthalenes","volume":"64","author":"Degtyarev","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1039\/b106725g","article-title":"Molecular structure of 5,6-bis(dimethylamino)acenaphthene, 5,6- bis(dimethylamino)acenaphthylene, and their monohydrobromides: A comparison with some naphthalene proton sponges","volume":"2","author":"Pozharskii","year":"2002","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2080","DOI":"10.1021\/ja00319a029","article-title":"General base catalysis, isotope effects, activation parameters, and the mechanism of removal of the hydrogen-bonded proton from protonated 1,8-bis(diethylamino)-2,7-dimethoxynaphthalene","volume":"106","author":"Barnett","year":"1984","journal-title":"J. Am. Chem. Soc."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"9932","DOI":"10.1002\/slct.202002745","article-title":"Synthesis of 2-Aryl- and 2,7-Diaryl-1,8-bis(dimethylamino)naphthalenes. Overview of the \u201cButtressing effect\u201d in 2,7-Disubstituted Proton Sponges","volume":"5","author":"Filatova","year":"2020","journal-title":"ChemistrySelect"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"10847","DOI":"10.1021\/acs.analchem.0c02545","article-title":"Proton Transfer Reactions for the Gas-Phase Separation, Concentration, and Identification of Cardiolipins","volume":"92","author":"Randolph","year":"2020","journal-title":"Anal. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"6977","DOI":"10.1021\/jo101381r","article-title":"A Colorimetric Proton Sponge","volume":"75","author":"Swor","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"2471","DOI":"10.1103\/PhysRevLett.55.2471","article-title":"Unified Approach for Molecular Dynamics and Density-Functional Theory","volume":"55","author":"Car","year":"1985","journal-title":"Phys. Rev. Lett."},{"doi-asserted-by":"crossref","unstructured":"Mitchell, P.C.H., Parker, S.F., Ramirez-Cuesta, A.J., and Tomkinson, J. (2005). Series on Neutron Techniques and Applications, Vibrational Spectroscopy with Neutrons, World Scientific Publishing Co. Pte. Ltd.","key":"ref_72","DOI":"10.1142\/5628"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"1795","DOI":"10.1351\/pac200173111795","article-title":"NMR nomenclature. Nuclear spin properties and conventions for chemical shifts (IUPAC recommendations 2001)","volume":"73","author":"Harris","year":"2001","journal-title":"Pure Appl. Chem."},{"unstructured":"Mestrelab Research, S.L. (2020, October 12). Available online: https:\/\/mestrelab.com\/software\/mnova.","key":"ref_74"},{"unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). et al. Gaussian 16, Revision \u0421.01, Gaussian, Inc.","key":"ref_75"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"5639","DOI":"10.1063\/1.438980","article-title":"Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11-18","volume":"72","author":"McLean","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1063\/1.438955","article-title":"Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions","volume":"72","author":"Krishnan","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"3265","DOI":"10.1063\/1.447079","article-title":"Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets","volume":"80","author":"Frisch","year":"1984","journal-title":"J. Chem. Phys."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1787","DOI":"10.1002\/jcc.20495","article-title":"Semiempirical GGA-type Density Functional Constructed with a Long-Range Dispersion Correction","volume":"27","author":"Grimme","year":"2006","journal-title":"J. Comput. Chem."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","article-title":"Quantum mechanical continuum solvation models","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Soc. Rev."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1023\/A:1008193805436","article-title":"Molden: A pre- and post-processing program for molecular and electronic structures","volume":"14","author":"Schaftenaar","year":"2000","journal-title":"J. Comput. Aided Mol. Design."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1887","DOI":"10.1021\/cr00031a008","article-title":"Perturbation Theory Approach to Intermolecular Potential Energy Surfaces of van der Waals Complexes","volume":"7","author":"Jeziorski","year":"1994","journal-title":"Chem. Rev."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"014101","DOI":"10.1063\/1.3451077","article-title":"Density fitting of intramonomer correlation effects in symmetry-adapted perturbation theory","volume":"133","author":"Hohenstein","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"6796","DOI":"10.1063\/1.462569","article-title":"Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions","volume":"96","author":"Kendall","year":"1992","journal-title":"J. Chem. Phys."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"3185","DOI":"10.1021\/acs.jctc.7b00174","article-title":"Psi4 1.1: An Open-Source Electronic Structure Program Emphasizing Automation, Advanced Libraries, and Interoperability","volume":"13","author":"Parrish","year":"2017","journal-title":"J. Chem. Theory Comput."},{"unstructured":"CPMD 3.17.1, 1997\u20132001.","key":"ref_88"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD\u2014Visual Molecular Dynamics","volume":"14","author":"Humphrey","year":"1996","journal-title":"J. Mol. Graph."},{"unstructured":"Gnuplot 4.2, 1986\u20131993, 1998, 2004, 2007.","key":"ref_90"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"3865","DOI":"10.1103\/PhysRevLett.77.3865","article-title":"Generalized Gradient Approximation Made Simple","volume":"77","author":"Perdew","year":"1996","journal-title":"Phys. Rev. Lett."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"1993","DOI":"10.1103\/PhysRevB.43.1993","article-title":"Efficient pseudopotentials for plane-wave calculations","volume":"B43","author":"Troullier","year":"1991","journal-title":"Phys. Rev."},{"key":"ref_93","first-page":"136","article-title":"The potential calculation and some applications","volume":"9","author":"Hockney","year":"1970","journal-title":"Meth. Comput. Phys."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"511","DOI":"10.1063\/1.447334","article-title":"A unified formulation of the constant temperature molecular dynamics methods","volume":"81","year":"1984","journal-title":"J. Chem. Phys."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1103\/PhysRevA.31.1695","article-title":"Canonical dynamics: Equilibrium phase-space distributions","volume":"A31","author":"Hoover","year":"1985","journal-title":"Phys. Rev."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"5105","DOI":"10.1021\/acs.chemrev.5b00533","article-title":"Dispersion-Corrected Mean-Field Electronic Structure Methods","volume":"116","author":"Grimme","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"3338","DOI":"10.1021\/acs.biochem.8b00217","article-title":"Hydrogen Bonds: Simple after All?","volume":"57","author":"Herschlag","year":"2018","journal-title":"Biochemistry"},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"5730","DOI":"10.1021\/ja512980h","article-title":"Determination of hydrogen bond structure in water versus aprotic environments to test the relationship between length and stability","volume":"137","author":"Sigala","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_99","first-page":"1129","article-title":"Neutron scattering in the biological sciences: Progress and prospects","volume":"D74","author":"Ashkar","year":"2018","journal-title":"Acta Cryst."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"3949","DOI":"10.1021\/jp004429o","article-title":"Inelastic Neutron Scattering:\u2009 A Tool in Molecular Vibrational Spectroscopy and a Test of ab Initio Methods","volume":"105","author":"Hudson","year":"2001","journal-title":"Phys. Chem. A"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/j.vibspec.2006.04.014","article-title":"Vibrational spectroscopy using inelastic neutron scattering: Overview and outlook","volume":"42","author":"Hudson","year":"2006","journal-title":"Vibr. Spectr."},{"doi-asserted-by":"crossref","unstructured":"V\u00e9rtes, A., Nagy, S., Klencs\u00e1r, Z., Lovas, R.G., and R\u00f6sch, F. (2011). Neutron Scattering Methods in Chemistry. Handbook of Nuclear Chemistry, Springer.","key":"ref_102","DOI":"10.1007\/978-1-4419-0720-2"},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/S0360-0564(06)51003-X","article-title":"IINS Inelastic Incoherent Neutron Scattering in Catalysis Research","volume":"51","author":"Albers","year":"2007","journal-title":"Adv. Catal."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"1032","DOI":"10.1021\/mp400707m","article-title":"Polymorphism of Paracetamol: A New Understanding of Molecular Flexibility through Local Methyl Dynamics","volume":"11","author":"Tsapatsaris","year":"2014","journal-title":"Mol. Pharm."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"154506","DOI":"10.1063\/1.2990650","article-title":"The structure, methyl rotation reflected in elestic and quasielastic neutron scattering and vibrational spectra of 1,2,3,5-tetramethoxybenzene and its 2:1 complex with 1,2,4,5-tetracyanobenzene","volume":"129","author":"Prager","year":"2008","journal-title":"J. Chem. Phys."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"2434","DOI":"10.1021\/mp2006032","article-title":"Application of Incoherent Inelastic Neutron Scattering in Pharmaceutical Analysis: Relaxation Dynamics in Phenacetin","volume":"9","author":"Bordallo","year":"2012","journal-title":"Mol. Pharm."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"1138","DOI":"10.1016\/S0921-4526(97)00810-7","article-title":"Vibrational dynamics of crystalline L-alanine","volume":"241-243","author":"Bordallo","year":"1998","journal-title":"Phys. B"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"766","DOI":"10.1016\/j.saa.2005.06.030","article-title":"Low frequency internal modes of 1,2,4,5-tetramethylbenzene, tetramethylpyrazine and tetramethyl-1,4-benzoquinone. INS, Raman, IR and theoretical DFT studies","volume":"63","author":"Natkaniec","year":"2006","journal-title":"Spectrochim. Acta A"},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"214509","DOI":"10.1063\/1.2803187","article-title":"Inelastic neutron scattering study of methyl groups rotation in some methylxanthines","volume":"127","author":"Prager","year":"2007","journal-title":"J. Chem. Phys."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"044509","DOI":"10.1063\/1.3613640","article-title":"4,4\u2019-, 5,5\u2019-, and 6,6\u2019-dimethyl-2,2\u2019-bipyridyls: The structures, phase transitions, vibrations, and methyl group tunneling of their complexes with chloranilic acid","volume":"135","author":"Bator","year":"2011","journal-title":"J. Chem. Phys."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1002\/jrs.4880","article-title":"Raman signatures of strong and weak hydrogen bonds in binary mixtures of phenol with acetonitrile, benzene and orthodichlorobenzene","volume":"47","author":"Singh","year":"2016","journal-title":"Raman Spectr."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1002\/jrs.1250070311","article-title":"Effects of hydrogen bonding on the Raman intensities of methanol, ethanol and water","volume":"7","author":"Abe","year":"1978","journal-title":"Raman Spectr."},{"unstructured":"Schuster, P., Zundel, G., and Sandorfy, C. (1976). The Hydrogen Bond. Recent Developments in Theory and Experiments, North-Holland.","key":"ref_113"},{"key":"ref_114","first-page":"1","article-title":"Hydrogen bonds with large proton polarizability and proton transfer processes in electrochemistry and biology","volume":"111","author":"Zundel","year":"2000","journal-title":"Adv. Chem. Phys."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"19467","DOI":"10.1039\/C8NJ04339F","article-title":"A molecular roundabout: Triple cycle-arranged hydrogen bonds in light of experiment and theory","volume":"42","author":"Kwocz","year":"2018","journal-title":"New J. Chem."},{"doi-asserted-by":"crossref","unstructured":"J\u00f3\u017awiak, K., Jezierska, A., Panek, J.J., Goremychkin, E.A., Tolstoy, P.M., Shenderovich, I.G., and Filarowski, A. (2020). Inter- vs. intra-molecular hydrogen bond patterns and proton dynamics in phthalic acid associates. Molecules, 25.","key":"ref_116","DOI":"10.3390\/molecules25204720"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/12\/11\/1924\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:35:52Z","timestamp":1760178952000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/12\/11\/1924"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,23]]},"references-count":116,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2020,11]]}},"alternative-id":["sym12111924"],"URL":"https:\/\/doi.org\/10.3390\/sym12111924","relation":{},"ISSN":["2073-8994"],"issn-type":[{"type":"electronic","value":"2073-8994"}],"subject":[],"published":{"date-parts":[[2020,11,23]]}}}