Around 1996, journals started publishing what became known as “ESI” or electronic supporting information, alongside the articles themselves, as a mechanism for exposing the data associated with the research being reported and exploiting some of the new opportunities offered by the World Wide Web. From the outset, such ESI was expressed as a paginated Acrobat file, with the Web being merely a convenient document delivery mechanism. Such ESI would eventually reach more than 1000 such pages in length in some chemistry articles. The richer opportunities of Web interactivity were far less exploited. I have written about various aspects of this throughout this blog[1],[2],[3], together with one early compendium of our own data examples.[4] Here I update that compendium starting from 2005 to the current 2023 and add further information, being the current state of curation of some of these early examples. Curation became necessary because many of the earlier examples were no longer functional due to changes in the way journals expose these data objects or indeed changes at the data repository end of things over this 18 year period.
| Table 1. Eighteen years of publishing journal FAIR data objects and their current curation location |
|||||
|---|---|---|---|---|---|
| # | Article DOIa | Year | Title | Article Data URL/ Data Citationa |
Curated version via DOI |
| 1 | 10.1021/ja043819b | 2005 | A Computational Analysis of the Ring-Opening Polymerization of rac-Lactide Initiated by Single-Site β-Diketiminate Metal Complexes: Defining the Mechanistic Pathway and the Origin of Stereocontrol |
Archive | Tables S1, S2 and S3 |
| 2 | 10.1039/b510508k | 2005 | Double-twist Möbius Aromaticity in a 4n+2 Electron Electrocyclic Reaction | Table S1 | Table S1 |
| 3 | 10.1021/ol0518333 | 2005 | A Double-Twist Möbius-Aromatic Conformation of [14]Annulene | Archive | Figure S1 |
| 4 | 10.1021/ja061400a | 2006 | Synthetic, Structural, Mechanistic, and Computational Studies on Single-Site β-Diketiminate Tin(II) Initiators for the Polymerization of rac-Lactide |
WEO | Table S1 |
| 5 | 10.1021/ic0519988 | 2006 | A Computational Study of the Nondissociative Mechanisms that Interchange Apical and Equatorial Atoms in Square Pyramidal Molecules |
Index for 14 WEOs | Index for 14 WEOs |
| 6 | 10.1021/ic062473y | 2007 | In Search of the Bailar and Rây−Dutt Twist Mechanisms That Racemize Chiral Trischelates: A Computational Study of ScIII, TiIV, CoIII, ZnII, GaIII, and GeIV Complexes of a Ligand Analogue of Acetylacetonate |
WEOa,WEOb,WEOc, WEOd,WEOe, WEOf |
Index to WEOa-f |
| 7 | 10.1021/ol703129z | 2008 | Lemniscular Hexaphyrins as Examples of Aromatic and Antiaromatic Double-Twist Möbius Molecules |
WEO | WEO |
| 8 | 10.1021/np0705918 | 2008 | Structural Reassignment of Obtusallenes V, VI, and VII by GIAO-Based Density Functional Prediction |
WEO | WEO |
| 9 | 10.1021/ja710438j | 2008 | Intrinsically Chiral Aromaticity. Rules Incorporating Linking Number, Twist, and Writhe for Higher-Twist Möbius Annulenes |
Archive,WEO1, WEO2, WEO3, WEO4 |
WEO1, WEO2, WEO3, WEO4 |
| 10 | 10.1021/jo801022b | 2008 | Chiral Aromaticities. AIM and ELF Critical Point and NICS Magnetic Analyses of Möbius-Type Aromaticity and Homoaromaticity in Lemniscular Annulenes and Hexaphyrins |
Archive, WEO | WEO |
| 11 | 10.1021/ct8001915 | 2008 | Chiral Aromaticities. A Topological Exploration of Möbius Homoaromaticity | Table 1 | Table 1 |
| 12 | 10.1039/b810147g | 2008 | A computational investigation of the structure of polythiocyanogen | Table 1 | Table 1 |
| 13 | 10.1039/B810301A | 2009 | Wormholes in chemical space connecting torus knot and torus link π-electron density topologies |
Table 1 | Table 1 |
| 14 | 10.1021/ol901172g | 2009 | The Chiro-optical Properties of a Lemniscular Octaphyrin | Table 1 | Table 1 |
| 15 | 10.1021/jp902176a | 2009 | The Geometry and Electronic Topology of Higher-Order Charged Möbius Annulenes | Table 1 | Table 1 |
| 16 | 10.1039/B911817A | 2009 | The distortivity of π-electrons in conjugated boron rings | Table 1 | Table 1 |
| 17 | 10.1038/nchem.373 | 2009 | The importance of being bonded | Exploratorium | Exploratorium |
| 18 | 10.1039/B913295C | 2009 | Unusual regiodivergence in metal-catalysed intramolecular cyclisation of γ-allenols | Tables 1 & 2 | Tables 1 & 2 |
| 19 | 10.1016/j.tetlet.2009.02.228 | 2009 | A dramatic effect of double bond configuration in N-oxy-3-aza Cope rearrangements—a simple synthesis of functionalised allenes |
Not hosted | Table |
| 20 | 10.1021/ed800058c | 2009 | Racemization of Isobornyl Chloride via Carbocations: A Nonclassical Look at a Classic Mechanism |
Table | Table |
| 21 | 10.1126/science.1181771 | 2010 | A Tricyclic Aromatic Isomer of Hexasilabenzene | Missing | Table |
| 22 | 10.1021/ol9024259 | 2010 | Stereoselective Synthesis of cis- and trans-2,3-Disubstituted Tetrahydrofurans via Oxonium−Prins Cyclization: Access to the Cordigol Ring System |
WEO, Archive | WEO |
| 23 | 10.1021/jo100920e | 2010 | Successful Computational Modeling of Isobornyl Chloride Ion-Pair Mechanisms | WEO | WEO |
| 24 | 10.1021/jo1002906 | 2010 | Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters |
WEO, Archive |
WEO |
| 25 | 10.1038/NCHEM.596 | 2010 | The rational design of helium bonds | Redirection | WEO |
| 26 | 10.1002/chem.201001087 | 2010 | Enantiomerically Pure Alleno–Acetylenic Macrocycles: Synthesis, Solid-State Structures, Chiroptical Properties, and Electron Localization Function Analysis |
Figure 9 | Figure 9 |
| 27 | 10.1021/ct100470g | 2011 | Nature of the Carbon−Sulfur Bond in the Species H−CS−OH | Archive, Table | Table |
| 28 | 10.1039/C0CC04023A | 2011 | Can 1,3-dimethylcyclobutadiene and carbon dioxide co-exist inside a supramolecular cavity? |
Table1 | Table 1 |
| 29 | 10.1021/ol2001705 | 2011 | Design, Synthesis, and Evaluation of a Helicenoidal DMAP Lewis Base Catalyst | Archive, WEO | WEO |
| 30 | 10.1186/1758-2946-3-46 | 2011 | The past, present and future of Scientific discourse | Archive, WEO | WEO |
| 31 | 10.1002/chem.201200547 | 2012 | Silver-Catalysed Enantioselective Addition of O-H and N-H Bonds to Allenes: A New Model for Stereoselectivity Based on Noncovalent Interactions |
Webtable1 | Web Table 1 |
| 32 | 10.1021/ma300803b | 2012 | Experimental and Computational Investigation of the Mechanism of Carbon Dioxide/Cyclohexene Oxide Copolymerization Using a Dizinc Catalyst |
Archive | Table 2, Table 3, Table 4, Table 5, Table 6 and Table 7 |
| 33 | 10.1039/C2CC33676F | 2012 | Verification of stereospecific dyotropic racemisation of enantiopure d and l-1,2-dibromo-1,2-diphenylethane in non-polar media |
Interactivity box | Interactivity box |
| 34 | 10.1002/chem.201102942 | 2013 | A Computational Evaluation of the Evidence for the Synthesis of 1,3-Dimethylcyclobutadiene in the Solid State and Aqueous Solution |
Web Table, Archive | Web Table |
| 36 | 10.1186/1758-2946-5-6 | 2013 | Chemical datuments as scientific enablers | Archive 1, Archive 2, Archive 3, Archive 4, | Datument |
| 37 | 10.1038/nchem.1751 | 2013 | Equilibrium between a cyclotrisilene and an isolable base adduct of a disilenyl silylene |
Archive | Interactivity box |
| 38 | 10.1186/1752-153X-7-94 | 2013 | N-heteroatom substitution effect in 3-aza-cope rearrangements | Archive | Table 1 |
| 39 | 10.1021/jo401146k | 2013 | Mechanistic Diversity in Thermal Fragmentation Reactions: A Computational Exploration of CO and CO2 Extrusions from Five-Membered Rings |
Archive, Interactivity box | Interactivity box |
| 40 | 10.1039/C3CC46720A | 2013 | Epoxidation of bromoallenes connects red algae metabolites by an intersecting bromoallene oxide – Favorskii manifold |
Interactivity box | Interactivity box |
| 41 | 10.1021/jo401316a | 2013 | Mechanistic and Chiroptical Studies on the Desulfurization of Epidithiodioxopiperazines Reveal Universal Retention of Configuration at the Bridgehead Carbon Atoms |
Archive, Interactivity box | Interactivity box |
| 42 | 10.1039/C3SC53416B | 2014 | The Houk–List transition states for organocatalytic mechanisms revisited | Archive 1, Archive 2, Archive 3, Archive 4, Archive 5, Archive 6, Archive 7, Table 1, Table 2, Table 3, Table 4, Table 6, Table 7, Table 8 |
Table 1, Table 2, Table 3, Table 4, Table 5, Table 6, Table 7, Table 8 |
| 43 | 10.1021/cs500326e | 2014 | Catalytic and Computational Studies of N-Heterocyclic Carbene or Phosphine-Containing Copper(I) Complexes for the Synthesis of 5-Iodo-1,2,3-Triazoles |
Archive 1, Archive 2, Archive 3, Archive 4, Archive 5, Table 1, Table 2, Table 3, Table 4, Table 5 |
Table 1, Table 2, Table 3, Table 4, Table 5 |
| 44 | 10.1002/anie.201405238 | 2014 | N-Heterocyclic Carbene Coordinated Neutral and Cationic Heavier Cyclopropylidenes | Archive | Imagemap |
| 45 | 10.1021/ci500302p | 2014 | Digital Data Repositories in Chemistry and Their Integration with Journals and Electronic Notebooks |
WEO 1, WEO 2, Redirect Redirect | WEO 1, WEO 2 |
| 46 | 10.1002/anie.201407751 | 2014 | A Multiply Functionalized Base-Coordinated GeII Compound and Its Reversible Dimerization to the Digermene |
Archive | Interactivity box |
| 47 | 10.1002/anie.201409672 | 2014 | Surfing π Clouds for Noncovalent Interactions: Arenes versus Alkenes | Archive | Table |
| 48 | 10.1021/om501286g | 2015 | A Molecular Complex with a Formally Neutral Iron Germanide Motif (Fe2Ge2) | Archive | Table |
| 49 | 10.1021/ed500398e | 2015 | Asymmetric Epoxidation: A Twinned Laboratory and Molecular Modeling Experiment for Upper-Level Organic Chemistry Students |
Archive | WEO |
| 50 | 10.1021/jo5022647 | 2015 | Chiroptical Studies on Brevianamide B: Vibrational and Electronic Circular Dichroism Confronted |
Archive | Table |
| 51 | 10.1021/acs.joc.5b00205 | 2015 | Modulation of Amide Bond Rotamers in 5-Acyl-6,7-dihydrothieno[3,2-c]pyridines | Archive | Table |
| 52 | 10.1002/jcc.23985 | 2015 | Noncatalytic bromination of benzene: A combined computational and experimental study | Archive | Table 2 |
| 53 | 10.1002/chir.22486 | 2015 | Chiroptical Properties of Streptorubin B: The Synergy Between Theory and Experiment | Archive | Interactive data table |
| 54 | 10.1021/jacs.5b13070 | 2016 | Chemoselective Polymerizations from Mixtures of Epoxide, Lactone, Anhydride, and Carbon Dioxide |
Archive | Collection, Figure 10, Figure 11 |
| 55 | 10.1039/C6CC06395K | 2016 | Stable bromoallene oxides | Ref 21 | Repository collection |
| 56 | 10.1021/acs.joc.6b02008 | 2016 | Epimeric Face-Selective Oxidations and Diastereodivergent Transannular Oxonium Ion Formation-Fragmentations: Computational Modelling & Total Syntheses of 12-Epoxyobtusallene IV, 12-Epoxyobtusallene II, Obtusallene X, Marilzabicycloallene C and Marilzabicycloallene D |
Ref 35,36 | Data Collection, Data Table |
| 57 | 10.1021/acs.orglett.7b00642 | 2017 | Total Synthesis of (+)-Lophirone H and Its Pentamethyl Ether Utilizing an Oxonium–Prins Cyclization |
Ref 29 | Data collection |
| 58 | 10.1002/anie.201700977 | 2017 | Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst |
Ref 32 | Data Collection |
| 59 | 10.1021/acsomega.7b00482 | 2017 | Synthesis and Reactions of 3,3′,4,4′-Tetrahydro-1H,1’H-2,2′-spirobi[quinoline] Derivatives |
Ref 28 | Data collection |
| 60 | 10.1039/C7SC03595K | 2018 | Mechanistic insights into boron-catalysed direct amidation reactions | Clickable Figures 9-13, Ref 29 | Data Collection, FAIR Data Table |
| 61 | 10.1002/chem.201800071 | 2018 | Molecular Complexes of Formally Neutral Iron Germanides Motif (Fe3Ge & Fe2Ge): Coordination Chemistry of Mono- and Dicoordinated Germanium(0) |
Ref 27 | Data collection |
| 62 | 10.1039/C8GC01797B | 2018 | Thermal Azide-Alkene Cycloaddition Reactions: Straightforward Multi-gram Access to Δ2-1,2,3-Triazolines in Deep Eutectic Solvents |
Ref 48 | Data collection |
| 64 | 10.1039/c8sc04302g | 2018 | Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes – a reaction at the ‘oxonium-Prins’ vs ‘ortho-quinone methide cycloaddition’ mechanistic nexus, |
Ref 22 | FAIR Data collection, FAIR Data Table |
| 65 | 10.1039/C9OB00607A | 2019 | Elevated Reaction Order of 1,3,5-tri-tert-butylbenzene Bromination as Evidence of Clustered Polybromide Transition State: a Combined Kinetic and Computational Study |
Ref 32 | FAIR Data collection, FAIR Data Table |
| 66 | 10.1002/adsc.201901614 | 2020 | Cycloaddition Reactions of Azides and Electron-Deficient Alkenes in Deep Eutectic Solvents: Pyrazolines, Aziridines and Other Surprises, |
Ref 20 | FAIR Data Collection |
| 67 | 10.1002/anie.202006283 | 2020 | Equilibrium Formation of Stable All-Silicon Versions of 1,3-Cyclobutandiyl | Ref 28 | Data Collection, FAIR Data collection |
| 68 | 10.1039/D0CC04190D | 2020 | Cycloparaphenylene Möbius Trefoils | Ref 44 | FAIR Data collection, FAIR Data table |
| 69 | 10.1038/s41467-021-21433-8 | 2021 | A Thermodynamic assessment of the reported room-temperature chemical synthesis of C2 |
Ref 11 | FAIR Data collection |
| 70 | 10.1039/D1CP02056K | 2021 | Routes involving no free C2 in the DFT-computed mechanistic model for the reported room-temperature chemical synthesis of C2 |
Refs 21,27,28,31,32 | FAIR Data collection, FAIR Table S1, FAIR Table S2 |
| 71 | 10.1021/acs.joc.0c02998 | 2021 | Diastereopreference of intermediates in aminocatalysis: understanding and application to the chiral resolution of lactols |
Ref 11 | FAIR data collection, FAIR Data table |
| 72 | 10.1039/D2CC01136K | 2022 | A Stereoselective Hydride Transfer Reaction with Contributions from Attractive Dispersion Force Control |
Refs 5,6 | FAIR Data collection, FAIR Data table |
| 73 | 10.1039/D2CP01214F | 2022 | A combined DFT-predictive and experimental exploration of the sensitivity towards nucleofuge variation in zwitterionic intermediates relating to mechanistic models for unimolecular chemical generation and trapping of free C2 and alternative bimolecular pathways involving no free C2 |
Refs 14,16 | FAIR Data collection, FAIR data table |
| 74 | 10.1021/acs.jnatprod.2c00749 | 2022 | (±)-Polysiphenol and other Analogues via Symmetrical Intermolecular Dimerizations: a Synthetic, Spectroscopic, Structural and Computational Study | Ref 20. | FAIR Data collection 1 |
| 75 | 10.1021/acs.orglett.2c03152 | 2022 | Pyrimidine nucleosides syntheses by late-stage base heterocyclization reactions | Data availability statement | FAIR Data collection, FAIR data table |
| 76 | 10.26434/chemrxiv-2023-jbb0r | 2022 | General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres | Data availability statement | FAIR Data collection, FAIR data table |
| 77 | 10.1139/cjc-2022-0255 | 2023 | Teaching FAIR in Computational Chemistry: Managing and publishing data using the twin tools of Compute Portals and Repositories | Data availability statement | FAIR Data collections referenced in article |
| 78 | 10.1002/anie.202304246 | 2023 | General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres | Ref 16. | FAIR Data collections referenced in article, FAIR data table |
| 79 | 10.1021/acs.inorgchem.3c01506 | 2023 | Syntheses and Characterization of Diverse Main Group, Transition, Lanthanide and Actinide Metal Complexes of Ethyl-3-Oxo-2,3-dihydro-1H-pyrazole-4-carboxylate and Related Bidentate Ligands | Ref 47 | FAIR Data collections referenced in article |
| 80 | 10.1021/acs.joc.3c00585 | 2023 | On the Use of Triarylsilanols as Catalysts for Direct Amidation of Carboxylic Acids | Ref 37 | FAIR Data collections referenced in article, FAIR data table |
| 81 | 10.26434/chemrxiv-2023-vcmcl | 2023 | SWERN Oxidation. Transition State Theory is OK | Ref 17 | FAIR Data collections referenced in article, FAIR data table |
aTo inspect the metadata associated with any article, use eg https://api.crossref.org/works/10.1002/anie.202006283/transform/application/vnd.crossref.unixsd+xml
and check how eg the data citation is expressed there.
The future seems likely to be influenced by the increasing requests from publishers for data to be made available in so-called FAIR-form, via an appropriate citation using a data DOI. The other feature on the horizon is the introduction of tools such as “Finding Aids“, where an automated script is able to automatically identify relationships between various data objects and the molecular content expressed within them and to generate a tool which exploits these relationships by adding further layers of navigation and especially of Findability to the data objects. I hope to show such an example here shortly – watch this space.
References
- H. Rzepa, "Four stages in the evolution of interactive ESI as part of articles in chemistry journals.", 2022. https://doi.org/10.59350/qypm4-qfv97
- H. Rzepa, "Web page decay and Journals: How an interactive "ESI" from 2006 was rescued.", 2022. https://doi.org/10.59350/cqesx-a0e83
- H. Rzepa, "Curating a nine year old journal FAIR data table.", 2017. https://doi.org/10.59350/z9g5j-r2p69
- H. Rzepa, "(Hyper)activating the chemistry journal.", 2009. https://doi.org/10.59350/wczky-8sf79