{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T04:12:56Z","timestamp":1790309576283,"version":"4.1.0"},"reference-count":84,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2021,2,20]],"date-time":"2021-02-20T00:00:00Z","timestamp":1613779200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The interactions of formaldehyde (FA), glyoxal (Gly) and methylglyoxal (MGly) with hydroxylamine (HA) isolated in solid argon and nitrogen were studied using FTIR spectroscopy and ab initio methods. The spectra analysis indicates the formation of two types of hydrogen-bonded complexes between carbonyl and hydroxylamine in the studied matrices. The cyclic planar complexes are stabilized by O\u2013H\u22efO(C), and C\u2013H\u22efN interactions and the nonplanar complexes are stabilized by O\u2013H\u22efO(C) bond. Formaldehyde was found to form with hydroxylamine, the cyclic planar complex and methylglyoxal, the nonplanar one in both argon and nitrogen matrices. In turn, glyoxal forms with hydroxylamine the most stable nonplanar complex in solid argon, whereas in solid nitrogen, both types of the complex are formed.<\/jats:p>","DOI":"10.3390\/molecules26041144","type":"journal-article","created":{"date-parts":[[2021,2,21]],"date-time":"2021-02-21T22:04:15Z","timestamp":1613945055000},"page":"1144","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Complexes of Formaldehyde and \u03b1-Dicarbonyls with Hydroxylamine: FTIR Matrix Isolation and Theoretical Study"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9818-1716","authenticated-orcid":false,"given":"Barbara","family":"Golec","sequence":"first","affiliation":[{"name":"Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44\/52, 01-224 Warsaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Magdalena","family":"Sa\u0142dyka","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zofia","family":"Mielke","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1943","DOI":"10.1063\/1.1739957","article-title":"Matrix isolation method for the experimental study of unstable species","volume":"22","author":"Whittle","year":"1954","journal-title":"J. Chem. Phys."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1007\/BF03155685","article-title":"Matrix isolation studies of reactive intermediate complexes","volume":"9","author":"Ault","year":"1988","journal-title":"Rev. Chem. Intermed."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.molstruc.2018.01.045","article-title":"Matrix isolation studies of hydrogen bonding\u2014An historical perspective","volume":"1163","author":"Barnes","year":"2018","journal-title":"J. Mol. Struct."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7986","DOI":"10.1021\/ja00833a026","article-title":"Evidence for two concurrent mechanisms and a kinetically significant proton transfer process in acid-catalyzed o-methyloxime formation","volume":"96","author":"Rosenberg","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"7998","DOI":"10.1021\/ja00833a027","article-title":"Mechanism of carbinolamine formation","volume":"96","author":"Sayer","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Lahann, J. (2009). Click Chemistry for Biotechnology and Materials Science, John Wiley and Sons Ltd.","DOI":"10.1002\/9780470748862"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Gauthier, M.A., and Klok, H.A. (2008). Peptide\/protein-polymer conjugates: Synthetic strategies and design concepts. Chem. Commun., 2591\u20132611.","DOI":"10.1039\/b719689j"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3712","DOI":"10.1021\/cr0502448","article-title":"Peptide conjugates of oligonucleotides: Synthesis and applications","volume":"106","author":"Venkatesan","year":"2006","journal-title":"Chem. Rev."},{"key":"ref_9","unstructured":"Hermanson, G.T. (2013). Bioconjugate Techniques, Elsevier. [3rd ed.]."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1007\/978-1-61779-151-2_20","article-title":"Conjugation of LPS-derived oligosaccharides to proteins using oxime chemistry","volume":"751","year":"2011","journal-title":"Methods Mol. Biol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"10358","DOI":"10.1021\/acs.chemrev.7b00090","article-title":"Oximes and hydrazones in bioconjugation: Mechanism and catalysis","volume":"117","author":"Kool","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_12","unstructured":"Lowry, T.H., and Schueller Richardson, K. (1987). Mechanism and Theory in Organic Chemistry, HarperCollins Publishers. [2nd ed.]."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1236","DOI":"10.1063\/1.1676210","article-title":"Molecular orbital studies of hydrogen bonds. III. C=O\u00b7\u00b7\u00b7H\u2013O hydrogen bond in H2CO\u00b7\u00b7\u00b7H2O and H2CO\u00b7\u00b7\u00b72H2O","volume":"55","author":"Morokuma","year":"1971","journal-title":"J. Chem. Phys."},{"key":"ref_14","first-page":"6517","article-title":"Molecular orbital theory of hydrogen bond. VI. Effect of hydrogen bonding on n-\u03c0* transitions in dimers ROHOCH2","volume":"2042","year":"1973","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1016\/0166-1280(90)80066-W","article-title":"Comparison of semiempirical and bsse corrected m\u00f8ller-plesset ab initio calculations on the direct addition of water to formaldehyde","volume":"210","author":"Ventura","year":"1990","journal-title":"J. Mol. Struct. Theochem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/jcc.540110102","article-title":"SCF, MP2 and CEPA-1 calculations on the OH-O hydrogen bonded complexes (H2O)2 and (H2O-H2CO)","volume":"11","author":"Vos","year":"1990","journal-title":"J. Comput. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/0301-0104(92)80077-9","article-title":"A matrix isolation study of the water-formaldehyde complex. The far-infrared region","volume":"159","author":"Nelander","year":"1992","journal-title":"Chem. Phys."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1037","DOI":"10.1002\/jcc.540130902","article-title":"Analysis of the gas-phase addition of water to formaldehyde: A semiempirical and ab initio study of bifunctional catalysis by H2O","volume":"13","author":"Ventura","year":"1992","journal-title":"J. Comput. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"11415","DOI":"10.1021\/j100146a013","article-title":"Ab initio study of the water-formaldehyde complex","volume":"97","author":"Ha","year":"1993","journal-title":"J. Phys. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"384","DOI":"10.1016\/0009-2614(94)00855-8","article-title":"Theoretical study of the n\u2192\u03c0* transitions in hydrogen-bonded formaldehyde complexes","volume":"227","author":"Dimitrova","year":"1994","journal-title":"Chem. Phys. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"15758","DOI":"10.1021\/j100043a012","article-title":"Solvent effects on optical emission and absorption spectra: Theoretical calculation of the 1(n, \u03c0*) transition of formaldehyde in solution","volume":"99","author":"Aguilar","year":"1995","journal-title":"J. Phys. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1016\/S0166-1280(96)04812-9","article-title":"Solvent effects on vibrational spectra of hydrogen-bonded complexes of formaldehyde and water: An ab initio study","volume":"391","author":"Dimitrova","year":"1997","journal-title":"J. Mol. Struct. Theochem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5796","DOI":"10.1021\/jp101157b","article-title":"Water complexes of important air pollutants: Geometries, complexation energies, concentrations, infrared spectra, and intrinsic reactivity","volume":"114","author":"Galano","year":"2010","journal-title":"J. Phys. Chem. A"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Ahlstr\u00f6m, M., J\u00f6nsson, B., and Karlstr\u00f6m, G. (1979). Ab initio molecular orbital calculations on hydrogen- and non-hydrogen-bonded complexes. H2CO\u00b7H2O and H2CO\u00b7H2S. Mol. Phys, 1051\u20131059.","DOI":"10.1080\/00268977900102231"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1063\/1.438922","article-title":"Infrared spectrum of the water formaldehyde complex in solid argon and solid nitrogen","volume":"72","author":"Nelander","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"6541","DOI":"10.1021\/ja00412a001","article-title":"Nuclear quadrupole coupling constants and hydrogen-bonding. A molecular-orbital study of O17 and deuterium field gradients in formaldehyde-water hydrogen bonding","volume":"103","author":"Butler","year":"1981","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1021\/ja00339a008","article-title":"Theoretical models for solvation and catalysis in carbonyl addition","volume":"105","author":"Williams","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1039\/f29888400893","article-title":"Theoretical studies of vibrational frequency shifts upon hydrogen bonding. The carbonyl stretching mode in complexes of formaldehyde","volume":"84","author":"Lewell","year":"1988","journal-title":"J. Chem. Soc. Faraday Trans. 2"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6948","DOI":"10.1021\/ja00200a009","article-title":"Solvent effects on optical absorption spectra: The 1A1\u20141A2 transition of formaldehyde in water","volume":"111","author":"Blair","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1016\/0009-2614(89)87146-5","article-title":"Simple-models for solvation effects on electronic-transition energies. Formaldehyde and water","volume":"154","author":"Blair","year":"1989","journal-title":"Chem. Phys. Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4478","DOI":"10.1021\/j100348a019","article-title":"Interaction of formaldehyde with water","volume":"93","author":"Kumpf","year":"1989","journal-title":"J. Phys. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/0022-2860(80)85264-1","article-title":"Infrared spectra of formaldehyde complexes with hydrogen bromide, chlorine and iodine chloride","volume":"69","author":"Nelander","year":"1980","journal-title":"J. Mol. Struct."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1016\/0022-2860(82)85334-9","article-title":"Infrared spectra and structure of formaldehyde complexes with ammonia and acetonitrile","volume":"81","author":"Nelander","year":"1982","journal-title":"J. Mol. Struct."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3509","DOI":"10.1063\/1.445174","article-title":"The rotational and hyperfine spectrum and structure of H2CO-HF","volume":"78","author":"Baiocchi","year":"1983","journal-title":"J. Chem. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3600","DOI":"10.1021\/j150660a044","article-title":"Infrared matrix isolation study of the hydrogen-bonded complexes between formaldehyde and the hydrogen halides and cyanide","volume":"88","author":"Bach","year":"1984","journal-title":"J. Phys. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1021\/jp7105154","article-title":"Lewis acid-base interactions in weakly bound formaldehyde complexes with CO2, HCN, and FCN: Considerations on the cooperative H-bonding effects","volume":"112","author":"Rivelino","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1217","DOI":"10.1002\/jcc.540111014","article-title":"The nature of the N-H O-C hydrogen bond\u2014An intermolecular perturbation theory study of the formamide\/formaldehyde complex","volume":"11","author":"Mitchell","year":"1990","journal-title":"J. Comput. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/S0301-0104(00)00053-7","article-title":"Thermodynamic, structural, and dynamic study of the N-H\u00b7\u00b7\u00b7O=C hydrogen bond association in aqueous solution","volume":"255","author":"Tolosa","year":"2000","journal-title":"Chem. Phys."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/0301-0104(82)88097-X","article-title":"Hydrogen-bonded complex between HNO and formaldehyde. Photolysis of methyl nitrite in an argon matrix","volume":"70","author":"Russegger","year":"1982","journal-title":"Chem. Phys."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"5379","DOI":"10.1021\/acs.jctc.7b00753","article-title":"C-H\u00b7\u00b7\u00b7O Hydrogen bonding. the prototypical methane-formaldehyde system: A critical assessment","volume":"13","author":"Moore","year":"2017","journal-title":"J. Chem. Theory Comput."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"9512","DOI":"10.1021\/jp020689p","article-title":"Controlled alcohol-ketone interconversion by dihydrogen transfer: An ab initio study of the methanol-formaldehyde complex","volume":"106","author":"Brumer","year":"2002","journal-title":"J. Phys. Chem. A"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2398","DOI":"10.1021\/jp066685s","article-title":"Complexes of atmospheric \u03b1-dicarbonyls with water: FTIR Matrix isolation and theoretical study","volume":"111","author":"Mucha","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1774","DOI":"10.1002\/cphc.200800249","article-title":"Photo-induced hydrogen exchange reaction between methanol and glyoxal: Formation of hydroxyketene","volume":"9","author":"Mielke","year":"2008","journal-title":"ChemPhysChem"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.chemphys.2009.05.005","article-title":"Structure and photochemistry of the methanol complexes with methylglyoxal and diacetyl: FTIR matrix isolation and theoretical study","volume":"361","author":"Mucha","year":"2009","journal-title":"Chem. Phys."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.cplett.2009.09.082","article-title":"Photochemistry of the glyoxal\u2013hydrogen peroxide complexes in solid argon: Formation of 2-hydroxy-2-hydroperoxyethanal","volume":"482","author":"Mucha","year":"2009","journal-title":"Chem. Phys. Lett."},{"key":"ref_46","unstructured":"Mucha, M. (2008). Faculty of Chemistry. [Ph.D. Thesis, University of Wroc\u0142aw]."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2492","DOI":"10.1021\/jp022636d","article-title":"Complexes of hydroperoxyl radical with glyoxal, methylglyoxal, methylvinyl ketone, acrolein, and methacrolein: Possible new sinks for HO2 in the atmosphere?","volume":"107","author":"Aloisio","year":"2003","journal-title":"J. Phys. Chem. A"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1016\/0022-2860(90)80370-Y","article-title":"The infrared spectrum of the hydroxylamine dimer","volume":"217","author":"Yeo","year":"1990","journal-title":"J. Mol. Struct."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/0924-2031(91)85023-G","article-title":"Matrix isolation infrared spectrum of the water-hydroxylamine complex","volume":"253","author":"Yeo","year":"1991","journal-title":"Vib. Spectrosc."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1016\/0584-8539(91)80281-M","article-title":"The matrix isolation infrared spectrum of the hydroxylamine-ammonia complex","volume":"47","author":"Yeo","year":"1991","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"4790","DOI":"10.1039\/B306785H","article-title":"Photodecomposition of formohydroxamic acid. Matrix isolation FTIR and DFT studies","volume":"5","author":"Mielke","year":"2003","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1922","DOI":"10.1039\/C2RA22694D","article-title":"Photodecomposition of N-hydroxyurea in argon matrices. FTIR and theoretical studies","volume":"3","year":"2013","journal-title":"RSC Adv."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1016\/0584-8539(73)80090-X","article-title":"Infrared and Raman spectra of formaldehyde in argon and nitrogen matrices","volume":"29","author":"Khoshkhoo","year":"1973","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1026","DOI":"10.1063\/1.440273","article-title":"Infrared spectrum of formaldehyde in solid nitrogen. I. Monomer absorption","volume":"73","author":"Nelander","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1034","DOI":"10.1063\/1.440274","article-title":"Infrared spectrum of formaldehyde in solid nitrogen. II. Dimer spectrum and dimer structure","volume":"73","author":"Nelander","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2155","DOI":"10.1021\/j100319a015","article-title":"Matrix infrared spectra and normal-coordinate analysis of isotopic hydroxylamine molecules","volume":"92","author":"Withnall","year":"1988","journal-title":"J. Phys. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1016\/0022-2860(68)87020-6","article-title":"Average structures of butadiene, acrolein, and glyoxal determined by gas electron diffraction and spectroscopy","volume":"1","author":"Kuchttsu","year":"1968","journal-title":"J. Mol. Struct."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4576","DOI":"10.1063\/1.441646","article-title":"Internal rotation barrier and transition state for glyoxal","volume":"74","author":"Osamura","year":"1981","journal-title":"J. Chem. Phys."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"2227","DOI":"10.1021\/j150615a018","article-title":"Photolysis and laser-excited fluorescence and phosphorescence emission of trans-glyoxal in an argon matrix at 13 K","volume":"85","author":"Diem","year":"1981","journal-title":"J. Phys. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"9886","DOI":"10.1021\/jp204532x","article-title":"Quantitative infrared intensity studies of vapor-phase glyoxal, methylglyoxal, and 2,3-butanedione (diacetyl) with vibrational assignments","volume":"115","author":"Profeta","year":"2011","journal-title":"J. Phys. Chem. A"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"4253","DOI":"10.1021\/cr990050q","article-title":"Blue-shifting hydrogen bonds","volume":"100","author":"Hobza","year":"2000","journal-title":"Chem. Rev."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"4695","DOI":"10.1021\/jp0143948","article-title":"Blue-shifting hydrogen bonds","volume":"106","author":"Hermansson","year":"2002","journal-title":"J. Phys. Chem. A"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.chemphys.2004.10.008","article-title":"Blue-shifted hydrogen-bonded complexes. II. CH3F\u00b7\u00b7\u00b7(HF)1\u2264n\u22643 and CH2F2\u00b7\u00b7\u00b7(HF)1\u2264n\u22643","volume":"310","author":"Karpfen","year":"2005","journal-title":"Chem. Phys."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1016\/j.chemphys.2006.04.006","article-title":"Theoretical study of Hal3CH\/F2CD2 (Hal=F,Cl) and F3CH\/FH heterodimers with blue shifted hydrogen bonds","volume":"327","author":"Rutkowski","year":"2006","journal-title":"Chem. Phys."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1016\/S0009-2614(01)01465-8","article-title":"Unusual spectroscopic properties of CF3H dissolved in liquified Ar, N2, CO and CO2","volume":"352","author":"Melikova","year":"2002","journal-title":"Chem. Phys. Lett."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/j.saa.2018.05.105","article-title":"The infrared study of fluoroform+methyl fluoride mixtures in argon and nitrogen matrices. Evidence of nonlinear blue-shifting complex formation","volume":"208","author":"Asfin","year":"2018","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/0301-0104(78)85114-3","article-title":"Microwave spectrum, dipole moment and barrier to internal rotation of trans-methyl glyoxal","volume":"30","author":"Bauder","year":"1978","journal-title":"Chem. Phys."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"7079","DOI":"10.1063\/1.458248","article-title":"A stimulated emission pumping study of jet-cooled methyl glyoxal","volume":"92","author":"Reid","year":"1990","journal-title":"J. Chem. Phys."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2597","DOI":"10.1021\/cr800346f","article-title":"What is the covalency of the hydrogen bonding?","volume":"111","author":"Grabowski","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"9747","DOI":"10.1021\/j100024a016","article-title":"Characterization of C-H-O hydrogen-bonds on the basis of the charge density","volume":"99","author":"Koch","year":"1995","journal-title":"J. Phys. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"e1480","DOI":"10.1002\/wcms.1480","article-title":"Decoding chemical information from vibrational spectroscopy data: Local vibrational mode theory","volume":"10","author":"Kraka","year":"2020","journal-title":"WIREs Comput. Mol. Sci."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/j.cplett.2012.10.047","article-title":"Local vibrational modes of the water dimer\u2014Comparison of theory and experiment","volume":"554","author":"Kalescky","year":"2012","journal-title":"Chem. Phys. Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1021\/acs.jctc.6b00735","article-title":"Different ways of hydrogen bonding in water\u2014Why does warm water freeze faster than cold water?","volume":"13","author":"Tao","year":"2017","journal-title":"J. Chem. Theory Comput."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1016\/j.cplett.2017.07.065","article-title":"Strengthening of hydrogen bonding with the push-pull effect","volume":"685","author":"Tao","year":"2017","journal-title":"Chem. Phys. Lett."},{"key":"ref_75","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_76","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_77","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1080\/00268977000101561","article-title":"Calculation of small molecular interactions by differences of separate total energies\u2014Some procedures with reduced errors","volume":"19","author":"Boys","year":"1970","journal-title":"Mol. Phys."},{"key":"ref_78","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, T., Kudin, K.N., and Burant, J.C. (2003). Gaussian 03, Revision, C.02, Gaussian Inc."},{"key":"ref_79","unstructured":"Keith, T.A. (2021, February 19). AIMAll, Version 12.09.23, Standard, 1997\u20132012. Available online: http:\/\/aim.tkgristmill.com."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1016\/j.molstruc.2012.05.020","article-title":"Matrix effects on hydrogen-bonded complexes trapped in low-temperature matrices","volume":"1023","author":"Barnes","year":"2012","journal-title":"J. Mol. Struct."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1865","DOI":"10.1002\/(SICI)1521-3765(20000515)6:10<1865::AID-CHEM1865>3.0.CO;2-9","article-title":"Dimerization of formic acid-an example of a \u201cnoncovalent\u201d reaction mechanism","volume":"6","author":"Gantenberg","year":"2000","journal-title":"Chem. Eur. J."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1016\/j.saa.2004.11.006","article-title":"Dimerization of the keto tautomer of acetohydroxamic acid\u2014Infrared matrix isolation and theoretical study","volume":"61","author":"Mielke","year":"2005","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.vibspec.2016.04.015","article-title":"N-Hydroxyurea dimers: A matrix isolation and theoretical study","volume":"85","year":"2016","journal-title":"Vib. Spectrosc."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1016\/j.saa.2017.09.046","article-title":"Structural and spectroscopic characterization of DMF complexes with nitrogen, carbon dioxide, ammonia and water. Infrared matrix isolation and theoretical studies","volume":"190","author":"Mielke","year":"2018","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/4\/1144\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:27:14Z","timestamp":1760160434000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/4\/1144"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,2,20]]},"references-count":84,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26041144"],"URL":"https:\/\/doi.org\/10.3390\/molecules26041144","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,2,20]]}}}