{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,31]],"date-time":"2026-10-31T02:21:34Z","timestamp":1793413294970,"version":"4.5.0"},"reference-count":46,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2020,6,1]],"date-time":"2020-06-01T00:00:00Z","timestamp":1590969600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2020,6,1]],"date-time":"2020-06-01T00:00:00Z","timestamp":1590969600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"funder":[{"DOI":"10.13039\/501100007685","name":"National Council for Tertiary Education","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100007685","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Journal of Molecular Graphics and Modelling"],"published-print":{"date-parts":[[2020,6]]},"DOI":"10.1016\/j.jmgm.2020.107542","type":"journal-article","created":{"date-parts":[[2020,1,21]],"date-time":"2020-01-21T09:02:29Z","timestamp":1579597349000},"page":"107542","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":19,"special_numbering":"C","title":["Peri-, Chemo-, Regio-, Stereo- and Enantio-Selectivities of 1,3-dipolar cycloaddition reaction of C,N-Disubstituted nitrones with disubstituted 4-methylene-1,3-oxazol-5(4H)- one: A quantum mechanical study"],"prefix":"10.1016","volume":"97","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4700-8005","authenticated-orcid":false,"given":"George Baffour","family":"Pipim","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4271-6838","authenticated-orcid":false,"given":"Ernest","family":"Opoku","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1043-8869","authenticated-orcid":false,"given":"Richard","family":"Tia","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2544-8883","authenticated-orcid":false,"given":"Evans","family":"Adei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.jmgm.2020.107542_bib1","first-page":"1","article-title":"Rolf huisgen, chemischen industric, dusscldorf","volume":"23","author":"Prof","year":"1961","journal-title":"Angew. Chern. Interntrf. Ed."},{"key":"10.1016\/j.jmgm.2020.107542_bib2","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1021\/cr950016l","article-title":"Transition metal-mediated cycloaddition reactions","volume":"96","author":"Lautens","year":"1996","journal-title":"Chem. Rev."},{"key":"10.1016\/j.jmgm.2020.107542_bib3","doi-asserted-by":"crossref","first-page":"5366","DOI":"10.1021\/cr5007182","article-title":"Recent advances of catalytic asymmetric 1,3-dipolar cycloadditions","volume":"115","author":"Hashimoto","year":"2015","journal-title":"Chem. Rev."},{"key":"10.1016\/j.jmgm.2020.107542_bib4","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/j.jmgm.2019.08.004","article-title":"1, 3-Dipolar cycloaddition reactions of selected 1,3-dipoles with 7-isopropylidenenorbornadiene and follow-up thermolytic cleavage: a computational study","volume":"92","author":"Arhin","year":"2019","journal-title":"J.\u00a0Mol. Graph. Model."},{"key":"10.1016\/j.jmgm.2020.107542_bib5","series-title":"The Mechanism of the Cycloaddition Reaction of 1 , 3-dipole Molecules with Acetylene\u00a0: an Investigation with the Unified Reaction Valley Approach","author":"Freindorf","year":"2014"},{"key":"10.1016\/j.jmgm.2020.107542_bib6","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1007\/s00214-019-2529-8","article-title":"Site-, enantio- and stereo-selectivities of the 1,3-dipolar cycloaddition reactions of oxanorbornadiene with C,N-disubstituted nitrones and dimethyl nitrilimines: a DFT mechanistic study","volume":"139","author":"Opoku","year":"2020","journal-title":"Theor. Chem. Acc."},{"key":"10.1016\/j.jmgm.2020.107542_bib7","doi-asserted-by":"crossref","first-page":"3581","DOI":"10.1016\/S0040-4020(03)00547-7","article-title":"A\u00a0DFT study on the 1,3-dipolar cycloaddition reactions of C-(methoxycarbonyl)-N-methyl nitrone with methyl acrylate and vinyl acetate","volume":"59","author":"Merino","year":"2003","journal-title":"Tetrahedron"},{"key":"10.1016\/j.jmgm.2020.107542_bib8","doi-asserted-by":"crossref","first-page":"11503","DOI":"10.1016\/j.tet.2004.09.057","article-title":"A\u00a0theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes","volume":"60","author":"Aurell","year":"2004","journal-title":"Tetrahedron"},{"key":"10.1016\/j.jmgm.2020.107542_bib9","first-page":"108","article-title":"Experimental and DFT studies for substituent effects on cycloadditions of C","volume":"57","author":"Mandal","year":"2018","journal-title":"N-disubstituted nitrones to cinnamoyl piperidine"},{"key":"10.1016\/j.jmgm.2020.107542_bib10","series-title":"Quantitative Characterization of the Local Electrophilicity of Organic Molecules","author":"Domingo","year":"2002"},{"issue":"131","key":"10.1016\/j.jmgm.2020.107542_bib11","doi-asserted-by":"crossref","first-page":"10187","DOI":"10.1021\/ja800009z","article-title":"Theory of 1 , 3-dipolar Cycloadditions\u00a0: distortion\/interaction and frontier molecular orbital models","volume":"130","author":"Ess","year":"2008","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2020.107542_bib12","doi-asserted-by":"crossref","first-page":"2072","DOI":"10.1186\/s40064-016-3758-0","article-title":"1,3-Dipolar [3\u00a0+ 2] cycloaddition reactions of N,C,C-trisubstituted nitrones with ring-acceptor methylenecyclopropanes: a computational study","volume":"5","author":"Mensah","year":"2016","journal-title":"SpringerPlus"},{"key":"10.1016\/j.jmgm.2020.107542_bib13","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1039\/B909358N","article-title":"Asymmetric 1,3-dipolar cycloadditions of acrylamides","volume":"39","author":"Kissane","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"10.1016\/j.jmgm.2020.107542_bib14","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.comptc.2018.10.002","article-title":"A\u00a0DFT mechanistic study of the generation of azomethine ylides from the ring-opening reactions of stabilized aziridines and follow-up 1,3-dipolar cycloaddition reactions with acetaldehyde, Comput","volume":"1144","author":"Nantogma","year":"2018","journal-title":"Theor. Chem."},{"issue":"8","key":"10.1016\/j.jmgm.2020.107542_bib15","doi-asserted-by":"crossref","first-page":"2887","DOI":"10.1021\/cr078371m","article-title":"Enantioselective copper-catalyzed 1 , 3-dipolar cycloadditions","volume":"108","author":"Stanley","year":"2008","journal-title":"Chem. Rev."},{"key":"10.1016\/j.jmgm.2020.107542_bib16","doi-asserted-by":"crossref","first-page":"4684","DOI":"10.1021\/acs.chemrev.8b00476","article-title":"Synthesis and transformations of nitrones for organic synthesis","volume":"119","author":"Murahashi","year":"2019","journal-title":"Chem. Rev."},{"key":"10.1016\/j.jmgm.2020.107542_bib17","doi-asserted-by":"crossref","first-page":"1077","DOI":"10.3987\/R-1987-04-1077","article-title":"Azlactones: retrospect and prospect","volume":"26","author":"Mukerjee","year":"1987","journal-title":"Heterocycles"},{"key":"10.1016\/j.jmgm.2020.107542_bib18","doi-asserted-by":"crossref","first-page":"456","DOI":"10.1002\/jhet.3419","article-title":"Reaction of 2-Phenyl-4-arylidene-1,3-oxazolones with different nucleophiles for synthesis of some new heterocycles","volume":"56","author":"Youssef","year":"2019","journal-title":"J.\u00a0Heterocycl. Chem."},{"issue":"17","key":"10.1016\/j.jmgm.2020.107542_bib19","doi-asserted-by":"crossref","first-page":"3270","DOI":"10.1021\/jo00138a014","article-title":"Synthesis of racemic (E)-and (Z)-1-amino-2-phenylcyclopropanecarboxylic acid:(E)-and (Z)-cyclopropylphenylalanine","volume":"47","author":"King","year":"1982","journal-title":"J.\u00a0Org. Chem."},{"issue":"5","key":"10.1016\/j.jmgm.2020.107542_bib20","first-page":"1397","article-title":"1, 3-Dipolar cycloaddition reactions of 2-phenyl-4-arylidene-5 (4H)-oxazolones with nitrile oxides","volume":"2","author":"Argyropoulos","year":"1984","journal-title":"J.\u00a0Het. Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib21","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.ica.2011.08.016","article-title":"Theoretical study of Re(IV) and Ru(II) bis-isocyanide complexes and their reactivity in cycloaddition reactions with nitrones","volume":"380","author":"Novikov","year":"2012","journal-title":"Inorg. Chim. Acta."},{"key":"10.1016\/j.jmgm.2020.107542_bib22","doi-asserted-by":"crossref","first-page":"2874","DOI":"10.1002\/chem.201203098","article-title":"Theory of The formation and decomposition of N-heterocyclic aminooxycarbenes through metal-assisted [2+3]-Dipolar cycloaddition\/retro-cycloaddition","volume":"19","author":"Novikov","year":"2013","journal-title":"Chem. Eur J."},{"key":"10.1016\/j.jmgm.2020.107542_bib23","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.jorganchem.2015.07.024","article-title":"1,3-Dipolar cycloaddition of nitrones to transition metal-bound isocyanides: DFT and HSAB principle theoretical model together with analysis of vibrational spectra","volume":"797","author":"Novikov","year":"2015","journal-title":"J.\u00a0Organomet. Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib24","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1039\/C5NJ02564H","article-title":"PdII-mediated integration of isocyanides and azide ions might proceed via formal 1,3-dipolar cycloaddition between RNC ligands and uncomplexed azide","volume":"40","author":"Kinzhalov","year":"2016","journal-title":"New J. Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib25","doi-asserted-by":"crossref","first-page":"3974","DOI":"10.1021\/acs.organomet.7b00591","article-title":"Tetrazol-5-ylidene gold(III) complexes from sequential [2\u00a0+ 3] cycloaddition of azide to metal-bound isocyanides and N4 alkylation","volume":"36","author":"Kinzhalov","year":"2017","journal-title":"Organometallics"},{"key":"10.1016\/j.jmgm.2020.107542_bib26","doi-asserted-by":"crossref","first-page":"3025","DOI":"10.1016\/j.tet.2017.04.014","article-title":"Regio- and diastereoselectivity of the cycloaddition of aldonitrones with benzylidenecyclopropane: an experimental and theoretical study","volume":"73","author":"Sirotkina","year":"2017","journal-title":"Tetrahedron"},{"key":"10.1016\/j.jmgm.2020.107542_bib27","doi-asserted-by":"crossref","first-page":"2327","DOI":"10.1016\/j.tetlet.2018.04.066","article-title":"Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates","volume":"59","author":"Dmitriev","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.jmgm.2020.107542_bib28","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1016\/j.tet.2017.11.056","article-title":"Regio- and diastereoselectivity of the cycloaddition of nitrones with N-propadienylindole and pyrroles","volume":"74","author":"Efremova","year":"2018","journal-title":"Tetrahedron"},{"key":"10.1016\/j.jmgm.2020.107542_bib29","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1515\/znb-2016-0263","article-title":"Regio- and stereoselective 1,3-dipolar cycloaddition reactions of C-aryl (or hetaryl)-N-phenylnitrones to monosubstituted ylidene malononitriles and 4-benzylidene-2-phenyloxazol-5(4H)-one","volume":"72","author":"Mekheimer","year":"2017","journal-title":"Zeitschrift Fur Naturforsch. - Sect. B J. Chem. Sci."},{"key":"10.1016\/j.jmgm.2020.107542_bib30","series-title":"Gaussian 09, Revision B. 01","author":"Frisch","year":"2009"},{"key":"10.1016\/j.jmgm.2020.107542_bib31","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1021\/ar700111a","article-title":"Density functionals with broad applicability in chemistry","volume":"41","author":"Zhao","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"10.1016\/j.jmgm.2020.107542_bib32","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1002\/anie.200502677","article-title":"The origin of the halogen effect on reactivity and reversibility of diels\u2013alder cycloadditions involving furan","volume":"45","author":"Pieniazek","year":"2006","journal-title":"Angew. Chem. Int. Ed."},{"key":"10.1016\/j.jmgm.2020.107542_bib33","doi-asserted-by":"crossref","first-page":"9335","DOI":"10.1021\/ja1009162","article-title":"Origins of stereoselectivity in the trans Diels\u2212Alder paradigm","volume":"132","author":"Paton","year":"2010","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2020.107542_bib34","doi-asserted-by":"crossref","first-page":"3895","DOI":"10.1021\/ja107988b","article-title":"Unraveling the mechanism of cascade reactions of zincke aldehydes","volume":"133","author":"Paton","year":"2011","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2020.107542_bib35","doi-asserted-by":"crossref","first-page":"10376","DOI":"10.1021\/jp9058565","article-title":"Accurate reaction enthalpies and sources of error in DFT thermochemistry for aldol, mannich, and \u03b1-aminoxylation reactions","volume":"113","author":"Wheeler","year":"2009","journal-title":"J.\u00a0Phys. Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib36","doi-asserted-by":"crossref","first-page":"982","DOI":"10.1002\/jcc.540100804","article-title":"Validation of the general purpose tripos 5.2 force field","volume":"10","author":"Clark","year":"1989","journal-title":"J.\u00a0Comput. Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib37","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. Rev."},{"key":"10.1016\/j.jmgm.2020.107542_bib38","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1007\/s00894-019-4056-x","article-title":"Computational studies on [4\u2009+\u20092]\/[3\u2009+\u20092] tandem sequential cycloaddition reactions of functionalized acetylenes with cyclopentadiene and diazoalkane for the formation of norbornene pyrazolines","volume":"25","author":"Opoku","year":"2019","journal-title":"J.\u00a0Mol. Model."},{"key":"10.1016\/j.jmgm.2020.107542_bib39","doi-asserted-by":"crossref","DOI":"10.1002\/poc.3992","article-title":"DFT mechanistic study on tandem sequential [4\u00a0+ 2]\/[3\u00a0+ 2] addition reaction of cyclooctatetraene with functionalized acetylenes and nitrile imines","author":"Opoku","year":"2019","journal-title":"J.\u00a0Phys. Org. Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib40","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/j.jmgm.2019.06.019","article-title":"Quantum chemical studies on the mechanistic aspects of tandem sequential cycloaddition reactions of cyclooctatetraene with ester and nitrones","volume":"92","author":"Opoku","year":"2019","journal-title":"J.\u00a0Mol. Graph. Model."},{"key":"10.1016\/j.jmgm.2020.107542_bib41","first-page":"10","article-title":"[ 3\u00a0+ 2 ] versus [ 2\u00a0+ 2 ] Addition\u00a0: a density functional theory study on the mechanistic aspects of transition metal-assisted formation of 1 , 2-dinitrosoalkanes","volume":"2016","author":"Opoku","year":"2016","journal-title":"J.\u00a0Chem."},{"key":"10.1016\/j.jmgm.2020.107542_bib42","doi-asserted-by":"crossref","DOI":"10.1016\/j.jmgm.2019.107452","article-title":"Mechanistic studies on tandem cascade [4\u00a0+ 2]\/[3\u00a0+ 2] cycloaddition of 1,3,4-oxadiazoles with olefins","volume":"93","author":"Roland","year":"2019","journal-title":"J.\u00a0Mol. Graph. Model."},{"key":"10.1016\/j.jmgm.2020.107542_bib43","author":"Legault"},{"key":"10.1016\/j.jmgm.2020.107542_bib44","doi-asserted-by":"crossref","first-page":"1922","DOI":"10.1021\/ja983494x","article-title":"Electrophilicity index","volume":"121","author":"Parr","year":"1999","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2020.107542_bib45","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/S0031-8914(34)90011-2","article-title":"\u00dcber die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms","volume":"1","author":"Koopmans","year":"1934","journal-title":"Physica"},{"key":"10.1016\/j.jmgm.2020.107542_bib46","doi-asserted-by":"crossref","first-page":"1486","DOI":"10.1039\/C2RA22886F","article-title":"Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions","volume":"3","author":"Domingo","year":"2013","journal-title":"RSC Adv."}],"container-title":["Journal of Molecular Graphics and Modelling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S1093326319310162?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S1093326319310162?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T21:01:59Z","timestamp":1761080519000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S1093326319310162"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,6]]},"references-count":46,"alternative-id":["S1093326319310162"],"URL":"https:\/\/doi.org\/10.1016\/j.jmgm.2020.107542","relation":{},"ISSN":["1093-3263"],"issn-type":[{"value":"1093-3263","type":"print"}],"subject":[],"published":{"date-parts":[[2020,6]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Peri-, Chemo-, Regio-, Stereo- and Enantio-Selectivities of 1,3-dipolar cycloaddition reaction of C,N-Disubstituted nitrones with disubstituted 4-methylene-1,3-oxazol-5(4H)- one: A quantum mechanical study","name":"articletitle","label":"Article Title"},{"value":"Journal of Molecular Graphics and Modelling","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.jmgm.2020.107542","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"107542"}}