{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,2]],"date-time":"2026-02-02T21:20:13Z","timestamp":1770067213799,"version":"3.49.0"},"reference-count":83,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2021,11,15]],"date-time":"2021-11-15T00:00:00Z","timestamp":1636934400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Computation"],"abstract":"<jats:p>Trimeric acylphloroglucinols (T-ACPLs) are a subclass of the large class of acylphloroglucinols\u2014derivatives of 1,3,5-trihydroxybenzene containing an R\u2013C=O group. T-ACPL molecules contain three acylphloroglucinol moieties linked by methylene bridges. Many of them are present in natural sources and exhibit biological activities, often better than the corresponding activities of monomeric acylphloroglucinols. All the stable conformers of T-ACPLs contain seven intramolecular hydrogen bonds, which constitute the dominant stabilising factors. A total of 38 different T-ACPLs, including both naturally occurring and model molecules, have been calculated at the HF and DFT\/B3LYP levels. The DFT\/B3LYP calculations were carried out both without and with Grimme\u2019s dispersion correction, to highlight the dispersion (and, therefore, also electron correlation) effects for these molecules. The roles of dispersion are evaluated considering the effects of Grimme\u2019s correction on the estimation of the conformers\u2019 energies, the description of the characteristics of the individual hydrogen bonds, the conformers\u2019 geometries and other molecular properties. Overall, the results offer a comprehensive overview of the conformational preferences of T-ACPL molecules, their intramolecular hydrogen bond patterns, and the correlation effects on their properties.<\/jats:p>","DOI":"10.3390\/computation9110121","type":"journal-article","created":{"date-parts":[[2021,11,15]],"date-time":"2021-11-15T08:19:20Z","timestamp":1636964360000},"page":"121","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Correlation Effects in Trimeric Acylphloroglucinols"],"prefix":"10.3390","volume":"9","author":[{"given":"Liliana","family":"Mammino","sequence":"first","affiliation":[{"name":"School of Mathematical and Natural Science, University of Venda, Thohoyandou 0950, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"558","DOI":"10.1039\/b600518g","article-title":"Phloroglucinol compounds of natural origin","volume":"23","author":"Singh","year":"2006","journal-title":"Nat. Prod. Rep."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1023\/A:1026069624278","article-title":"Are acylphloroglucinols lead structures for the treatment of degenerative diseases?","volume":"1","author":"Verotta","year":"2002","journal-title":"Phytochem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"7830","DOI":"10.1039\/D0NJ06114J","article-title":"Toward an efficient and eco-friendly route for the synthesis of dimeric 2,4-diacetyl phloroglucinol and its potential as a SARS-CoV-2 main protease antagonist: Insight from in silico studies","volume":"45","author":"Kusumaningsih","year":"2021","journal-title":"New J. Chem."},{"key":"ref_4","unstructured":"Bushelyev, S.N., and Stepanov, N.F. (1989). Elektronnaya Struktura y Biologhicheskaya Aktivnost Molecul, Khimiya, Snanye."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.theochem.2006.10.019","article-title":"Model structures for the study of acylated phloroglucinols and computational study of the caespitate molecule","volume":"805","author":"Mammino","year":"2007","journal-title":"J. Mol. Struct. (Theochem)"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1016\/j.theochem.2009.01.032","article-title":"A study of the intramolecular hydrogen bond in acylphloroglucinols","volume":"901","author":"Mammino","year":"2009","journal-title":"J. Mol. Struct. (Theochem)"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3691","DOI":"10.1002\/qua.24012","article-title":"The conformational preferences of acylphloroglucinols\u2014A promising class of biologically active compounds","volume":"112","author":"Kabanda","year":"2012","journal-title":"Int. J. Quantum Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2650","DOI":"10.1002\/qua.23280","article-title":"Computational study of the patterns of weaker intramolecular hydrogen bonds stabilizing acylphloroglucinols","volume":"112","author":"Mammino","year":"2012","journal-title":"Int. J. Quantum Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/08927022.2012.700483","article-title":"The role of additional O\u2013H\u00b7\u00b7\u00b7O intramolecular hydrogen bonds for acylphloroglucinols\u2019 conformational preferences in vacuo and in solution","volume":"39","author":"Mammino","year":"2013","journal-title":"Mol. Simul."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2378","DOI":"10.1002\/qua.22704","article-title":"Adducts of acylphloroglucinols with explicit water molecules: Similarities and differences across a sufficiently representative number of structures","volume":"110","author":"Mammino","year":"2010","journal-title":"Int. J. Quantum Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"488","DOI":"10.1016\/j.molstruc.2018.07.013","article-title":"Intramolecular hydrogen bonding patterns, conformational preferences and molecular properties of dimeric acylphloroglucinols: An ab initio and DFT study","volume":"1176","author":"Mammino","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1016\/j.theochem.2003.11.050","article-title":"A theoretical and experimental study on the structure and dipole moment of phloroglucinol in ethanol","volume":"673","author":"Rudyk","year":"2004","journal-title":"J. Mol. Struct. (Theochem)"},{"key":"ref_13","first-page":"222","article-title":"Reactivity sites in dopamine depend on its intramolecular hydrogen bond","volume":"61","author":"Hernandez","year":"2017","journal-title":"J. Mex. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"301","DOI":"10.1016\/0968-0004(87)90146-0","article-title":"The hydrogen bond in molecular recognition","volume":"12","author":"Fersht","year":"1987","journal-title":"Trend. Biochem. Sci."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1038\/35086640","article-title":"Chemistry Beyond the Molecule","volume":"412","author":"Desiraju","year":"2001","journal-title":"Nature"},{"key":"ref_16","first-page":"4191","article-title":"The influence of an intramolecular hydrogen bod in a differential recognition of inhibitory acceptor analogs by human ABO(H) blood group A and B glycosyltransferases","volume":"49","author":"Nguyen","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Sanchez, G. (2019). Introduction to \u201cIntramolecular Hydrogen Bonding 2018\u201d. Molecules, 24.","DOI":"10.3390\/molecules24162858"},{"key":"ref_18","first-page":"24","article-title":"It is important to compute intramolecular hydrogen bonding in drug design?","volume":"5","author":"Yunta","year":"2017","journal-title":"Am. J. Model. Optim."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2343","DOI":"10.1039\/C5NJ02552D","article-title":"Evaluating the role of electron-correlation in the external prediction of the toxicity of nitrobenzenes towards Tetrahymena pyriformis","volume":"40","author":"Reenu","year":"2016","journal-title":"New J. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1039\/B615319B","article-title":"Density functional theory with dispersion corrections for supramolecular structures, aggregates, and complexes of (bio)organic molecules","volume":"5","author":"Grimme","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1380","DOI":"10.1021\/jz500165u","article-title":"Electrostatic domination of the effect of electron correlation in intermolecular interactions","volume":"5","author":"Thirman","year":"2014","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1937","DOI":"10.1021\/acs.jpclett.7b00535","article-title":"Quantifying electron correlation of the chemical bond","volume":"8","author":"Mcdonagh","year":"2017","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1021\/ct301065f","article-title":"The importance of electron correlation on stacking interaction of adenine-thymine base-pair step in B-DNA: A quantum Monte Carlo study","volume":"12","author":"Hongo","year":"2013","journal-title":"J. Chem. Theory Comput."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/jcc.540110102","article-title":"SCF, MP2, and CEPA-1 calculations on the OH \u2025 O hydrogen bonded complexes (H2O)2 and (H2O-H2CO)","volume":"11","author":"Vos","year":"1990","journal-title":"J. Comp. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"6628","DOI":"10.1063\/1.463666","article-title":"Cooperative (nonpairwise) effects in water trimers: An ab initio molecular orbital study","volume":"97","author":"Elguero","year":"1992","journal-title":"J. Chem. Phys."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1016\/0009-2614(93)85498-D","article-title":"Ab initio study of the gas-phase equilibrium between (H2O) 4 and (H2O) 8","volume":"212","author":"Ferrari","year":"1993","journal-title":"Chem. Phys. Lett."},{"key":"ref_27","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":"1998","journal-title":"Phys. Rev. B"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1372","DOI":"10.1063\/1.464304","article-title":"A new mixing of Hartree-Fock and local density-functional theories","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_29","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_30","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1016\/j.theochem.2007.02.033","article-title":"Competitive H-bonds in vacuo and in aqueous solution for N-protonated adrenaline and its monohydrated complexes","volume":"811","author":"Alagona","year":"2007","journal-title":"J. Mol. Struct. (Theochem)"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"e1800852","DOI":"10.1080\/00268976.2020.1800852","article-title":"Stacking interactions in cavity-containing molecular structures built from acylphloroglucinols: A computational study","volume":"119","author":"Mammino","year":"2020","journal-title":"Mol. Phys."},{"key":"ref_32","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_33","doi-asserted-by":"crossref","first-page":"3397","DOI":"10.1039\/b704725h","article-title":"Double-hybrid density functionals with long-range dispersion corrections: Higher accuracy and extended applicability","volume":"9","author":"Schwabe","year":"2007","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"124115","DOI":"10.1063\/1.2712433","article-title":"Analytic derivatives for perturbatively corrected \u201cdouble hybrid\u201d density functionals: Theory, implementation, and applications","volume":"126","author":"Neese","year":"2007","journal-title":"J. Chem. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1002\/wcms.30","article-title":"Density functional theory with London dispersion corrections","volume":"1","author":"Grimme","year":"2011","journal-title":"Wiley Interdiscip. Rev. WIREs Comput. Mol. Sci."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1456","DOI":"10.1002\/jcc.21759","article-title":"Effect of the damping function in dispersion corrected density functional theory","volume":"32","author":"Grimme","year":"2011","journal-title":"J. Comput. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"13942","DOI":"10.1039\/c1cp20591a","article-title":"Comparison of the performance of dispersion-corrected density functional theory for weak hydrogen bonds","volume":"13","author":"Hujo","year":"2011","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"886","DOI":"10.1002\/wcms.1110","article-title":"Spin-component-scaled electron correlation methods","volume":"2","author":"Grimme","year":"2012","journal-title":"WIREs Comput. Mol. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"9955","DOI":"10.1002\/chem.201200497","article-title":"Supramolecular binding thermodynamics by dispersion-corrected density functional theory","volume":"18","author":"Grimme","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"16031","DOI":"10.1039\/c3cp52293h","article-title":"Effects of London dispersion correction in density functional theory on the structures of organic molecules in the gas phase","volume":"15","author":"Grimme","year":"2013","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"916","DOI":"10.1021\/ar3000844","article-title":"Dispersion-corrected density functional theory for aromatic interactions in complex systems","volume":"46","author":"Ehrlich","year":"2013","journal-title":"Acc. Chem. Res."},{"key":"ref_42","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_43","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). Gaussian 16, Revision B.01, Gaussian, Inc."},{"key":"ref_44","unstructured":"(2006). GaussView 4.1, Gaussian Inc."},{"key":"ref_45","unstructured":"(2003). Chem3D, Chemoffice, Cambridge Software. Version 8.0.3."},{"key":"ref_46","unstructured":"Allouche, A.R. (2021, October 10). Gabedit. Available online: http:\/\/gabedit.sourceforge.net\/."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"191","DOI":"10.3891\/acta.chem.scand.17-0191","article-title":"The structures of filixic acid","volume":"17","author":"Penttila","year":"1963","journal-title":"Acta Chem. Scand."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1111\/j.2042-7158.1970.tb08551.x","article-title":"The chemistry of Dryopteris acylphloroglucinols","volume":"22","author":"Penttila","year":"1970","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2881","DOI":"10.1016\/S0031-9422(00)86531-0","article-title":"Phloroglucinol derivatives of Dryoptehs Dicklensi and some related ferns","volume":"11","author":"Hisada","year":"1972","journal-title":"Phytochemistry"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1493","DOI":"10.1016\/0031-9422(73)80592-8","article-title":"Isolation of flavaspidic acid-PB from Dryopteris sieboldii","volume":"12","author":"Hisada","year":"1973","journal-title":"Phytochemistry"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2055","DOI":"10.1016\/S0031-9422(00)91535-8","article-title":"Phloroglucinol derivatives of Dryopteris Szeboldzi","volume":"12","author":"Hisada","year":"1973","journal-title":"Phytochemistry"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1200","DOI":"10.3891\/acta.chem.scand.28b-1200","article-title":"Phloroglucinol derivatives of Hagenia abyssinica. II. The structure determination of kosotoxin and protokosin","volume":"28","author":"Lounasmaa","year":"1974","journal-title":"Acta Chem. Scand."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/S0031-9422(00)89031-7","article-title":"Phloroglucinol derivatives in Dryopterzs chrysocoma","volume":"15","author":"Puri","year":"1976","journal-title":"Phytochemistry"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1453","DOI":"10.1016\/0031-9422(82)80168-4","article-title":"A phloroglucinol derivative of Dryopteris Abbreviata","volume":"21","author":"Coskun","year":"1982","journal-title":"Phytochemistry"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3305","DOI":"10.1016\/0031-9422(91)83198-T","article-title":"Phloroglucinol derivatives from Dryopteris fusco-atra and d. hawaizensis","volume":"30","author":"Patama","year":"1991","journal-title":"Phytochemistry"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1016\/0731-7085(92)80080-7","article-title":"Evaluation of the anti-tumour action and acute toxicity of kosins from Hagenia abyssinica","volume":"10","author":"Woldemariam","year":"1992","journal-title":"Pharm. Biomed. Anal."},{"key":"ref_57","first-page":"69","article-title":"Phloroglucinol derivatives in Driopteris sect Fibrillosae and related taxa (Pteridophyta, Dryopteridaceae)","volume":"33","author":"Widen","year":"1996","journal-title":"Ann. Bot. Fenn."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1","DOI":"10.7439\/ijpp.v1i1.156","article-title":"Isolation and HPLC method development for filixic acid PBP from Dryopteris filix-mas","volume":"1","author":"Katekhaye","year":"2011","journal-title":"Int. J. Phytopharm."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"3345","DOI":"10.3390\/molecules19033345","article-title":"Compounds from Dryopteris Fragrans (L.) Schott with Cytotoxic Activity","volume":"19","author":"Zhao","year":"2014","journal-title":"Molecules"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1002\/bmc.3299","article-title":"Development of a liquid chromatography-mass spectrometry method for determination of agrimol B in rat plasma: Application to preclinical pharmacokinetics","volume":"29","author":"Wang","year":"2015","journal-title":"Biomed. Chromatogr."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1002\/cbdv.201400157","article-title":"Phytochemical constituents and biological activities of plants from the genus Dryopteris","volume":"12","author":"Han","year":"2015","journal-title":"Chem. Biodivers."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/j.bbrc.2016.06.078","article-title":"Agrimol B suppresses adipogenesis through modulation of SIRT1-PPAR gamma signal pathway","volume":"477","author":"Wang","year":"2016","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Wang, J., Yan, Y., Fu, S., Peng, B., Bao, L., Zhang, Y., Hu, J., Zeng, Z., Geng, D., and Gao, Z. (2017). Anti-Influenza Virus (H5N1) Activity Screening on the Phloroglucinols from Rhizomes of Dryopteris crassirhizoma. Molecules, 22.","DOI":"10.3390\/molecules22030431"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"107780","DOI":"10.1016\/j.exppara.2019.107780","article-title":"Ultrastructure changes induced by the phloroglucinol derivative agrimol G isolated from Leucosidea sericea in Haemonchus contortus","volume":"207","author":"Adamu","year":"2019","journal-title":"Exp. Parasitol."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1186\/s13071-019-3537-1","article-title":"An appraisal of natural products active against parasitic nematodes of animals","volume":"12","author":"Sleebs","year":"2019","journal-title":"Parasites Vectors"},{"key":"ref_66","doi-asserted-by":"crossref","unstructured":"Yim, N., Lee, J., Lee, B.H., Li, W., and Ma, J.Y. (2019). Antiplatelet activity of acylphloroglucinol derivatives isolated from Dryopteris crassirhizoma. Molecules, 24.","DOI":"10.3390\/molecules24122212"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"111795","DOI":"10.1016\/j.biopha.2021.111795","article-title":"Agrimol B present in Agrimonia pilosa Ledeb impedes cell cycle progression of cancer cells through G0 state arrest","volume":"141","author":"SHnit","year":"2021","journal-title":"Biomed. Pharmacother."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2254","DOI":"10.1080\/00268976.2017.1306127","article-title":"Bowl-shaped structures from acylphloroglucinols: An ab initio and DFT study","volume":"115","author":"Mammino","year":"2017","journal-title":"Mol. Phys."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1007\/s00894-019-4208-z","article-title":"Five- and six-member bowl-shaped structures from acylphloroglucinols: An ab initio and DFT study","volume":"26","author":"Mammino","year":"2020","journal-title":"J. Mol. Model."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"100283","DOI":"10.1016\/j.scp.2020.100283","article-title":"Computational chemistry for green design in chemistry and pharmacy: Building awareness in the classroom","volume":"18","author":"Mammino","year":"2020","journal-title":"Sustain. Chem. Pharm."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"9074","DOI":"10.1021\/ja0257319","article-title":"Crystalstructure and hydrogen-bonding system in cellulose I\u03b2 from synchrotron X-ray and neutron fiber diffraction","volume":"124","author":"Nishiyama","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_72","first-page":"840","article-title":"Carbohydrate hydrogen-bonding cooperativity\u2014Intramolecular hydrogen bonds and their cooperative effect on intermolecular processes\u2014Binding to a Hydrogen-bond acceptor molecule","volume":"5","author":"Ellis","year":"2002","journal-title":"Eur. J. Org. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"312","DOI":"10.1021\/jp076316b","article-title":"Intramolecular Hydrogen bonding and cooperative interactions in carbohydrates via the molecular tailoring approach","volume":"112","author":"Deshmukh","year":"2008","journal-title":"J. Chem. Phys. A"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"6036","DOI":"10.1063\/1.1400142","article-title":"Energetics and cooperativity in three-center hydrogen bonding interactions. II. Intramolecular hydrogen bonding systems","volume":"115","author":"Parra","year":"2001","journal-title":"J. Chem. Phys."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"14846","DOI":"10.1021\/ja028539f","article-title":"Hydrophobic interaction and hydrogen bonding cooperatively confer a vancomycin hydrogel: A potential candidate for biomaterials","volume":"124","author":"Xing","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"24152","DOI":"10.1021\/jp0543072","article-title":"Carbohydrate intramolecular hydrogen bonding cooperativity and its effect on water structure","volume":"109","author":"Dashnau","year":"2005","journal-title":"J. Phys. Chem. B"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"41576","DOI":"10.1074\/jbc.R112.418574","article-title":"Carbon-oxygen hydrogen bonding in biological structure and function","volume":"287","author":"Horowitz","year":"2012","journal-title":"J. Biol. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1021\/ja00185a035","article-title":"Evidence for resonance-assisted hydrogen bonding from crystal-structure correlations on the enol form of the beta-diketone fragment","volume":"111","author":"Gilli","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"4917","DOI":"10.1021\/ja00013a030","article-title":"Evidence for resonance-assisted hydrogen bonding. 2. Intercorrelation between crystal structure and spectroscopic parameters in eight intramolecularly hydrogen bonded 1, 3-diaryl-1, 3-propanedione enols","volume":"113","author":"Bertolasi","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref_80","doi-asserted-by":"crossref","unstructured":"Guevara-Vela, J.M., Gallegos, M., Valentin-Rodriguez, M.A., Costales, A., Rocha-Rinza, T., and Pend\u00e1s, A.M. (2021). On the relationships between hydrogen bond strength and the formation energy in resonance-assisted hydrogen bonds. Molecules, 26.","DOI":"10.3390\/molecules26144196"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1813","DOI":"10.1021\/acs.jpca.7b12635","article-title":"Nature of intramolecular resonance assisted hydrogen bonding in malonalehyde and its saturated analogue","volume":"122","author":"Grosch","year":"2018","journal-title":"J. Phys. Chem. A"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"9411","DOI":"10.1021\/ja991795g","article-title":"Fundamental properties of the CH\u00b7\u00b7\u00b7O interaction: Is it a true hydrogen bond?","volume":"121","author":"Gu","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1021\/ar950135n","article-title":"The C-H\u00b7\u00b7\u00b7O hydrogen bond: Structural implications and supramolecular design","volume":"29","author":"Desiraju","year":"1996","journal-title":"Acc. Chem. Res."}],"container-title":["Computation"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2079-3197\/9\/11\/121\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:30:19Z","timestamp":1760167819000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2079-3197\/9\/11\/121"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,15]]},"references-count":83,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2021,11]]}},"alternative-id":["computation9110121"],"URL":"https:\/\/doi.org\/10.3390\/computation9110121","relation":{},"ISSN":["2079-3197"],"issn-type":[{"value":"2079-3197","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,15]]}}}