{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:24:21Z","timestamp":1790727861019,"version":"4.1.0"},"reference-count":69,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2023,6,28]],"date-time":"2023-06-28T00:00:00Z","timestamp":1687910400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>A single crystal X-ray diffraction analysis was performed on two positional isomers (<jats:italic>m<\/jats:italic>-tolyl and <jats:italic>p<\/jats:italic>-tolyl) of acrylonitrile derivatives, namely, (Z)-3-(4-(pyridin-2-yl) phenyl)-2-(m-tolyl) acrylonitrile (<jats:bold>1<\/jats:bold>) and (Z)-3-(4-(pyridin-2-yl)phenyl)-2-(p-tolyl) acrylonitrile (<jats:bold>2<\/jats:bold>). Compound <jats:bold>1<\/jats:bold> crystallized in the monoclinic <jats:italic>P<\/jats:italic>2<jats:sub>1<\/jats:sub>\/n space group with two crystallographically independent molecules. Compound <jats:bold>2<\/jats:bold> also possesses two crystallographically independent molecules and crystallized in the triclinic <jats:italic>P<\/jats:italic>-1 space group. The Hirshfeld surface analysis revealed that, in both isomers, intermolecular H\u22c5\u22c5\u22c5H\/C\/N contacts contribute significantly to the crystal packing. More than 40% of the contribution arises from intermolecular C\u2013H\u22c5\u22c5\u22c5C(\u03c0) contacts. In both compounds, the relative contribution of these contacts is comparable, indicating that the positional isomeric effects are marginal. The structures in which these isomers are arranged in the solid state are very similar, and the lattice energies are also comparable between the isomers. The Coulomb-London-Pauli-PIXEL (CLP-PIXEL) energy analysis identified the energetically significant dimers. The strength of the intra- and intermolecular interactions was evaluated using the quantum theory of atoms in molecules approach. The UV-Vis absorbance in three different solvents (chloroform, ethanol, and ethyl acetate) for isomers <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> are very similar. This result is in good agreement with the time-dependent density-functional theory (TD-DFT) calculations.<\/jats:p>","DOI":"10.3389\/fchem.2023.1209428","type":"journal-article","created":{"date-parts":[[2023,6,28]],"date-time":"2023-06-28T12:13:20Z","timestamp":1687954400000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":13,"title":["Weak noncovalent interactions in two positional isomers of acrylonitrile derivatives: inputs from PIXEL energy, Hirshfeld surface and QTAIM analyses"],"prefix":"10.3389","volume":"11","author":[{"given":"M. Judith","family":"Percino","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mani","family":"Udayakumar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Margarita","family":"Cer\u00f3n","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Enrique","family":"P\u00e9rez-Guti\u00e9rrez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Perumal","family":"Venkatesan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Subbiah","family":"Thamotharan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2023,6,28]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"127019","DOI":"10.1016\/j.molstruc.2019.127019","article-title":"Insights into the weak Csp3\u2013H\u00b7\u00b7\u00b7H\u2013Csp3 mediated supramolecular architecture in ethyl 2-(5-bromopentanamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate, a probable selective COX-2 lead molecule: An integrated crystallographic and theoretical approach","volume":"1199","author":"Al-Ghulikah","year":"2020","journal-title":"J. Mol. Struct."},{"key":"B2","doi-asserted-by":"publisher","first-page":"658","DOI":"10.3390\/90800658","article-title":"Synthesis of substituted stilbenes via the Knoevenagel condensation","volume":"9","author":"Al-Shihry","year":"2004","journal-title":"Molecules"},{"key":"B3","doi-asserted-by":"publisher","first-page":"893","DOI":"10.1021\/cr00005a013","article-title":"A quantum theory of molecular structure and its applications","volume":"91","author":"Bader","year":"1991","journal-title":"Chem. Rev."},{"key":"B4","doi-asserted-by":"publisher","first-page":"5567","DOI":"10.1021\/acs.chemrev.5b00648","article-title":"Modeling polymorphic molecular crystals with electronic structure theory","volume":"116","author":"Beran","year":"2016","journal-title":"Chem. Rev."},{"key":"B5","doi-asserted-by":"publisher","first-page":"553","DOI":"10.1080\/00268977000101561","article-title":"The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors","volume":"19","author":"Boys","year":"1970","journal-title":"Mol. Phys."},{"key":"B6","doi-asserted-by":"publisher","first-page":"1785","DOI":"10.1021\/jz500755u","article-title":"Accurate modeling of organic molecular crystals by dispersion-corrected density functional tight binding (DFTB)","volume":"5","author":"Brandenburg","year":"2014","journal-title":"J. Phys. Chem. Lett."},{"key":"B7","doi-asserted-by":"publisher","first-page":"1804","DOI":"10.1039\/C7QM00157F","article-title":"Controlling solid-state optical properties of stimuli responsive dimethylamino-substituted dibenzoylmethane materials","volume":"1","author":"Butler","year":"2017","journal-title":"Mater. Chem. Front."},{"key":"B8","doi-asserted-by":"publisher","first-page":"481","DOI":"10.3389\/fchem.2018.00481","article-title":"Research progress on photosensitizers for DSSC","volume":"6","author":"Carella","year":"2018","journal-title":"Front. Chem."},{"key":"B9","doi-asserted-by":"publisher","first-page":"134674","DOI":"10.1016\/j.molstruc.2022.134674","article-title":"Non-covalent interactions towards 2-(4-(2,2-dicyanovinyl) benzylidene)malononitrile packing polymorphism due to solvent effect. Experimental and theoretical spectroscopy approach","volume":"1275","author":"Castillo","year":"2023","journal-title":"J. Mol. Struct."},{"key":"B10","doi-asserted-by":"publisher","first-page":"887","DOI":"10.1107\/S0108767395007367","article-title":"The analytical calculation of absorption in multifaceted crystals","volume":"51","author":"Clark","year":"1995","journal-title":"Acta Crystallogr. Sect. A"},{"key":"B11","doi-asserted-by":"publisher","first-page":"625","DOI":"10.1021\/ct100641a","article-title":"Nciplot: A program for plotting non-covalent interaction regions","volume":"7","author":"Contreras-Garc\u00eda","year":"2011","journal-title":"J. Chem. Theory Comput."},{"key":"B12","doi-asserted-by":"publisher","first-page":"669","DOI":"10.1002\/jcc.10189","article-title":"Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model","volume":"24","author":"Cossi","year":"2003","journal-title":"J. Comput. Chem."},{"key":"B13","doi-asserted-by":"crossref","DOI":"10.1142\/8060","volume-title":"Crystal engineering","author":"Desiraju","year":"2011"},{"key":"B14","doi-asserted-by":"publisher","first-page":"13878","DOI":"10.1039\/D1SC04017K","article-title":"Self-assembled cationic organic nanosheets: Role of positional isomers in a guanidinium-core for efficient lithium-ion conduction","volume":"12","author":"Dey","year":"2021","journal-title":"Chem. Sci."},{"key":"B15","doi-asserted-by":"publisher","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Crystallogr."},{"key":"B16","doi-asserted-by":"publisher","first-page":"9840","DOI":"10.1039\/D0RA00733A","article-title":"Quantitative assessment of the nature of noncovalent interactions in N-substituted-5-(adamantan-1-yl)-1,3,4-thiadiazole-2-amines: Insights from crystallographic and QTAIM analysis","volume":"10","author":"El-Emam","year":"2020","journal-title":"RSC Adv."},{"key":"B17","doi-asserted-by":"publisher","first-page":"170","DOI":"10.1016\/S0009-2614(98)00036-0","article-title":"Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities","volume":"285","author":"Espinosa","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"B18","doi-asserted-by":"crossref","DOI":"10.1002\/9783527634408","volume-title":"Molecular switches","author":"Feringa","year":"2011"},{"key":"B19","doi-asserted-by":"publisher","first-page":"923","DOI":"10.1021\/cr0501590","article-title":"Introduction: organic electronics and optoelectronics","volume":"107","author":"Forrest","year":"2007","journal-title":"Chem. Rev."},{"key":"B20","doi-asserted-by":"publisher","first-page":"121","DOI":"10.1038\/16393","article-title":"Electroluminescence in conjugated polymers","volume":"397","author":"Friend","year":"1999","journal-title":"Electroluminescence conjugated Polym."},{"key":"B21","doi-asserted-by":"publisher","first-page":"275","DOI":"10.1016\/0009-2614(90)80029-D","article-title":"A direct MP2 gradient method","volume":"166","author":"Frisch","year":"1990","journal-title":"Chem. Phys. Lett."},{"key":"B22","volume-title":"Gaussian 09, revision D.01","author":"Frisch","year":"2013"},{"key":"B23","doi-asserted-by":"publisher","first-page":"3399","DOI":"10.1039\/C9TC00348G","article-title":"Recent developments in stimuli-responsive luminescent films","volume":"7","author":"Gao","year":"2019","journal-title":"J. Mater. Chem. C"},{"key":"B24","doi-asserted-by":"publisher","first-page":"4145","DOI":"10.1021\/jp0144202","article-title":"Calculation of intermolecular interaction energies by direct numerical integration over electron densities. I. Electrostatic and polarization energies in molecular crystals","volume":"106","author":"Gavezzotti","year":"2002","journal-title":"J. Phys. Chem. B"},{"key":"B25","doi-asserted-by":"publisher","first-page":"2344","DOI":"10.1021\/jp022288f","article-title":"Calculation of intermolecular interaction energies by direct numerical integration over electron densities. 2. An improved polarization model and the evaluation of dispersion and repulsion energies","volume":"107","author":"Gavezzotti","year":"2003","journal-title":"J. Phys. Chem. B"},{"key":"B26","doi-asserted-by":"publisher","first-page":"499","DOI":"10.1524\/zkri.220.5.499.65063","article-title":"Calculation of lattice energies of organic crystals: The PIXEL integration method in comparison with more traditional methods","volume":"220","author":"Gavezzotti","year":"2005","journal-title":"Z. f\u00fcr Krist. - Cryst. Mater."},{"key":"B27","doi-asserted-by":"publisher","first-page":"1360","DOI":"10.1039\/C0NJ00982B","article-title":"Efficient computer modeling of organic materials. The atom\u2013atom, Coulomb\u2013London\u2013Pauli (AA-CLP) model for intermolecular electrostatic-polarization, dispersion and repulsion energies","volume":"35","author":"Gavezzotti","year":"2011","journal-title":"New J. Chem."},{"key":"B28","doi-asserted-by":"publisher","first-page":"4027","DOI":"10.1039\/C3CE00051F","article-title":"The \u201csceptical chymist\u201d: Intermolecular doubts and paradoxes","volume":"15","author":"Gavezzotti","year":"2013","journal-title":"CrystEngComm"},{"key":"B29","doi-asserted-by":"publisher","first-page":"5818","DOI":"10.1039\/C3TC31062K","article-title":"Luminescent distyrylbenzenes: Tailoring molecular structure and crystalline morphology","volume":"1","author":"Gierschner","year":"2013","journal-title":"J. Mater. Chem. C"},{"key":"B30","doi-asserted-by":"publisher","first-page":"348","DOI":"10.1002\/adom.201500531","article-title":"Organic single crystal lasers: A materials view","volume":"4","author":"Gierschner","year":"2016","journal-title":"Adv. Opt. Mater."},{"key":"B31","doi-asserted-by":"publisher","first-page":"2002251","DOI":"10.1002\/adom.202002251","article-title":"Luminescence in crystalline organic materials: From molecules to molecular solids","volume":"9","author":"Gierschner","year":"2021","journal-title":"Adv. Opt. Mater."},{"key":"B32","doi-asserted-by":"publisher","first-page":"154104","DOI":"10.1063\/1.3382344","article-title":"A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu","volume":"132","author":"Grimme","year":"2010","journal-title":"J. Chem. Phys."},{"key":"B33","doi-asserted-by":"publisher","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":"B34","doi-asserted-by":"publisher","first-page":"5675","DOI":"10.1002\/anie.201911531","article-title":"Impact of positional isomerism on pathway complexity in aqueous media","volume":"59","author":"Helmers","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"B35","doi-asserted-by":"publisher","first-page":"11013","DOI":"10.1039\/C9SC05012D","article-title":"The origin of the solvent dependence of fluorescence quantum yields in dipolar merocyanine dyes","volume":"10","author":"Hoche","year":"2019","journal-title":"Chem. Sci."},{"key":"B36","doi-asserted-by":"publisher","first-page":"218","DOI":"10.1039\/C9NJ03693H","article-title":"Perturbing the AIEE activity of pyridine functionalized \u03b1-cyanostilbenes with donor substitutions: An experimental and DFT study","volume":"44","author":"Jana","year":"2020","journal-title":"New J. Chem."},{"key":"B37","doi-asserted-by":"publisher","first-page":"5885","DOI":"10.1039\/D0CS00037J","article-title":"Organic solid-state lasers: A materials view and future development","volume":"49","author":"Jiang","year":"2020","journal-title":"Chem. Soc. Rev."},{"key":"B38","volume-title":"AIMAll, ver. 19.02.13","author":"Keith","year":"2019"},{"key":"B39","doi-asserted-by":"publisher","first-page":"12823","DOI":"10.1021\/acs.chemrev.6b00172","article-title":"Organic lasers: Recent developments on materials, device geometries, and fabrication techniques","volume":"116","author":"Kuehne","year":"2016","journal-title":"Chem. Rev."},{"key":"B40","doi-asserted-by":"publisher","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"B41","doi-asserted-by":"publisher","first-page":"226","DOI":"10.1107\/S1600576719014092","article-title":"Mercury 4.0: From visualization to analysis, design and prediction","volume":"53","author":"Macrae","year":"2020","journal-title":"J. Appl. Crystallogr."},{"key":"B42","doi-asserted-by":"publisher","first-page":"10034","DOI":"10.1002\/anie.201709766","article-title":"Visible-light photocatalysis: Does it make a difference in organic synthesis?","volume":"57","author":"Marzo","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"B43","doi-asserted-by":"publisher","first-page":"1940","DOI":"10.1002\/chem.200204626","article-title":"Hydrogen\u2013hydrogen bonding: A stabilizing interaction in molecules and crystals","volume":"9","author":"Matta","year":"2003","journal-title":"Chem. \u2013 A Eur. J."},{"key":"B44","doi-asserted-by":"publisher","first-page":"2727","DOI":"10.1039\/C9RA09576D","article-title":"A slight bluish-white fluorescence from E,E-2,6-bis(4-cyanostyryl)pyridine pristine crystals","volume":"10","author":"Mochizuki","year":"2020","journal-title":"RSC Adv."},{"key":"B45","doi-asserted-by":"publisher","first-page":"448","DOI":"10.1021\/acsomega.9b02962","article-title":"Modulation of weak interactions in structural isomers: Positional isomeric effects on crystal packing and physical properties and solid-state thin-film fabrication","volume":"5","author":"MonikaVerma","year":"2020","journal-title":"ACS Omega"},{"key":"B46","doi-asserted-by":"publisher","first-page":"74","DOI":"10.1016\/j.molstruc.2014.04.088","article-title":"Important role of molecular packing and intermolecular interactions in two polymorphs of (Z)-2-phenyl-3-(4-(pyridin-2-yl)phenyl)acrylonitrile. Preparation, structures, and optical properties","volume":"1078","author":"Percino","year":"2014","journal-title":"J. Mol. Struct."},{"key":"B47","doi-asserted-by":"publisher","first-page":"2889","DOI":"10.1002\/chem.200500850","article-title":"Hydrogen\u2013hydrogen bonding in planar biphenyl, predicted by atoms-in-molecules theory, does not exist","volume":"12","author":"Poater","year":"2006","journal-title":"Chem. \u2013 A Eur. J."},{"key":"B48","doi-asserted-by":"publisher","first-page":"1073","DOI":"10.1021\/cc070073f","article-title":"Combinatorial Knoevenagel reactions","volume":"9","author":"Ryabukhin","year":"2007","journal-title":"J. Comb. Chem."},{"key":"B49","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"71","author":"Sheldrick","year":"","journal-title":"Acta Crystallogr. Sect. C"},{"key":"B50","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT - integrated space-group and crystal-structure determination","volume":"71","author":"Sheldrick","year":"","journal-title":"Acta Crystallogr. Sect. A"},{"key":"B51","doi-asserted-by":"publisher","first-page":"1006","DOI":"10.1107\/S1600576721002910","article-title":"CrystalExplorer: A program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Crystallogr."},{"key":"B52","doi-asserted-by":"publisher","first-page":"148","DOI":"10.1107\/S090744490804362X","article-title":"Structure validation in chemical crystallography","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Crystallogr. Sect. D."},{"key":"B53","volume-title":"Aggregation-induced emission: Applications","author":"Tang","year":"2013"},{"key":"B54","doi-asserted-by":"publisher","first-page":"37","DOI":"10.1016\/0025-5408(68)90023-8","article-title":"Optical properties and electronic structure of amorphous Ge and Si","volume":"3","author":"Tauc","year":"1968","journal-title":"Mater. Res. Bull."},{"key":"B55","doi-asserted-by":"publisher","first-page":"11079","DOI":"10.1039\/C4CC04972A","article-title":"Molecular crystals by design?","volume":"50","author":"Tiekink","year":"2014","journal-title":"Chem. Commun."},{"key":"B56","doi-asserted-by":"publisher","first-page":"499","DOI":"10.1107\/S2056989019003694","article-title":"Quantitative analysis of weak non-covalent interactions in (Z)-3-(4-chlorophenyl)-2-phenylacrylonitrile: Insights from PIXEL and Hirshfeld surface analysis","volume":"75","author":"Udayakumar","year":"","journal-title":"Acta Crystallogr. Sect. E"},{"key":"B57","doi-asserted-by":"publisher","first-page":"32","DOI":"10.1016\/j.molstruc.2019.05.109","article-title":"Interplay of weak noncovalent interactions in two conjugated positional isomers: A combined X-ray, optical properties and theoretical investigation","volume":"1195","author":"Udayakumar","year":"","journal-title":"J. Mol. Struct."},{"key":"B58","doi-asserted-by":"publisher","first-page":"60","DOI":"10.1007\/s12039-019-1636-3","article-title":"A quantitative study of weak noncovalent interactions in two pyridine isomers containing nitrile and thiophene moieties: A combined X-ray and theoretical investigation","volume":"131","author":"Udayakumar","year":"","journal-title":"J. Chem. Sci."},{"key":"B59","doi-asserted-by":"publisher","first-page":"128174","DOI":"10.1016\/j.molstruc.2020.128174","article-title":"Correlation between structural and optical properties of \u03c0-conjugated acrylonitrile derivatives: Insights from X-ray, energy frameworks, TD-DFT and charge density analysis","volume":"1213","author":"Udayakumar","year":"2020","journal-title":"J. Mol. Struct."},{"key":"B60","doi-asserted-by":"publisher","first-page":"2681","DOI":"10.1039\/C7CE02096A","article-title":"Quantitative analysis of weak non-covalent interactions in (Z)-3-(4-halophenyl)-2-(pyridin-2\/3\/4-yl)acrylonitriles","volume":"20","author":"Venkatesan","year":"2018","journal-title":"CrystEngComm"},{"key":"B61","doi-asserted-by":"publisher","first-page":"2174","DOI":"10.1039\/C7QM00201G","article-title":"Molecular conformation and packing: Their critical roles in the emission performance of mechanochromic fluorescence materials","volume":"1","author":"Wang","year":"2017","journal-title":"Mater. Chem. Front."},{"key":"B62","doi-asserted-by":"publisher","first-page":"7834","DOI":"10.1039\/C3CS60102A","article-title":"Luminescent probes and sensors for temperature","volume":"42","author":"Wang","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"B63","doi-asserted-by":"publisher","first-page":"734","DOI":"10.1039\/D1TC04401J","article-title":"Reversible luminescence \u201coff\u2013on\u201d regulation based on tunable photodimerization via crystal-to-cocrystal transformation","volume":"10","author":"Wang","year":"2022","journal-title":"J. Mater. Chem. C"},{"key":"B64","doi-asserted-by":"publisher","first-page":"3086","DOI":"10.1002\/anie.201205133","article-title":"Highly fluorescent semiconducting polymer dots for biology and medicine","volume":"52","author":"Wu","year":"2013","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"B65","doi-asserted-by":"publisher","first-page":"2661","DOI":"10.1039\/C6CC04901J","article-title":"Molecular stacking dependent phosphorescence\u2013fluorescence dual emission in a single luminophore for self-recoverable mechanoconversion of multicolor luminescence","volume":"53","author":"Wu","year":"2017","journal-title":"Chem. Commun."},{"key":"B66","doi-asserted-by":"publisher","first-page":"46","DOI":"10.1039\/C3MH00023K","article-title":"Molecular crystalline materials with tunable luminescent properties: From polymorphs to multi-component solids","volume":"1","author":"Yan","year":"2014","journal-title":"Mater. Horizons"},{"key":"B67","doi-asserted-by":"publisher","first-page":"48777","DOI":"10.1039\/C7RA09131A","article-title":"Reversible mechanofluorochromism and acidochromism using a cyanostyrylbenzimidazole derivative with aggregation-induced emission","volume":"7","author":"Zhan","year":"2017","journal-title":"RSC Adv."},{"key":"B68","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","article-title":"The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals","volume":"120","author":"Zhao","year":"2008","journal-title":"Theor. Chem. Acc."},{"key":"B69","doi-asserted-by":"publisher","first-page":"2001","DOI":"10.1080\/00397910802632530","article-title":"Efficient Knoevenagel condensation catalyzed by 2-hydroxyethylammonium acetate under solvent-free conditions at room temperature","volume":"39","author":"Zhou","year":"2009","journal-title":"Synth. Commun."}],"container-title":["Frontiers in Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2023.1209428\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,6,28]],"date-time":"2023-06-28T12:13:28Z","timestamp":1687954408000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2023.1209428\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,6,28]]},"references-count":69,"alternative-id":["10.3389\/fchem.2023.1209428"],"URL":"https:\/\/doi.org\/10.3389\/fchem.2023.1209428","relation":{},"ISSN":["2296-2646"],"issn-type":[{"value":"2296-2646","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,6,28]]},"article-number":"1209428"}}