Automated Building of Organometallic Complexes from 3D Fragments

Foscato, Marco; Venkatraman, Vishwesh; Occhipinti, Giovanni; Alsberg, Bjørn K.; Jensen, Vidar R.

doi:10.1021/ci5003153

Cited by 35Computational Drug Discovery MethodsOrganometallic Complex Synthesis and CatalysisAdvanced Chemical Physics Studies

Automated Building of Organometallic Complexes from 3D Fragments

Foscato, Marco, Venkatraman, Vishwesh, Occhipinti, Giovanni, Alsberg, Bjørn K., Jensen, Vidar R.·2014·Journal of Chemical Information and Modeling

DOI 10.1021/ci5003153

Open this paper in CoChat — free account

Abstract

A method for the automated construction of three-dimensional (3D) molecular models of organometallic species in design studies is described. Molecular structure fragments derived from crystallographic structures and accurate molecular-level calculations are used as 3D building blocks in the construction of multiple molecular models of analogous compounds. The method allows for precise control of stereochemistry and geometrical features that may otherwise be very challenging, or even impossible, to achieve with commonly available generators of 3D chemical structures. The new method was tested in the construction of three sets of active or metastable organometallic species of catalytic reactions in the homogeneous phase. The performance of the method was compared with those of commonly available methods for automated generation of 3D models, demonstrating higher accuracy of the prepared 3D models in general, and, in particular, a much wider range with respect to the kind of chemical structures that can be built automatically, with capabilities far beyond standard organic and main-group chemistry.

Integrity signals

Registry

Crossref · 10.1021/ci5003153

Cites

72 of 72 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

This paper’s full text isn’t openly available, so its claims and self-check weren’t run. The registry and citation checks still apply.

Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
Miyaura, N., & Suzuki, A. (1995) · Chemical Reviews · doi:10.1021/cr00039a007 · Cited by 12,878 · see citing works
Open Babel: An open chemical toolbox
O'Boyle, N. M., Banck, M. S., James, C. A. J., Morley, C., Vandermeersch, T., & Hutchison, G. R. (2011) · Journal of Cheminformatics · doi:10.1186/1758-2946-3-33 · Cited by 10,705 · see citing works
UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations
Rappé, A. K., Casewit, C. J., Colwell, K. S., Goddard, W. A., & Skiff, W. M. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00051a040 · Cited by 10,603 · see citing works
The Development of L 2 X 2 RuCHR Olefin Metathesis Catalysts: An Organometallic Success Story
Trnka, T. M., & Grubbs, R. H. (2000) · Accounts of Chemical Research · doi:10.1021/ar000114f · Cited by 3,561 · see citing works
Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands
Scholl, M., Ding, S., Lee, C. W., & Grubbs, R. H. (1999) · Organic Letters · doi:10.1021/ol990909q · Cited by 3,469 · see citing works
Olefin Metathesis-Active Ruthenium Complexes Bearing a Nucleophilic Carbene Ligand
Huang, J., Stevens, E. D., Nolan, S. P., & Petersen, J. L. (1999) · Journal of the American Chemical Society · doi:10.1021/ja9831352 · Cited by 1,011 · see citing works
The remarkable metal-catalysed olefin metathesis reaction
Hoveyda, A. H., & Zhugralin, A. R. (2007) · Nature · doi:10.1038/nature06351 · Cited by 1,009 · see citing works
Progress in hydroformylation and carbonylation
Beller, M., Cornils, B., Frohning, C. D., et al. (1995) · Journal of Molecular Catalysis A Chemical · doi:10.1016/1381-1169(95)00130-1 · Cited by 877 · see citing works
Hydroformylation of alkenes by use of rhodium complex catalysts
Evans, D., Osborn, J. A., & Wilkinson, G. R. (1968) · Journal of the Chemical Society A Inorganic Physical Theoretical · doi:10.1039/j19680003133 · Cited by 682 · see citing works
Comparison of Automatic Three-Dimensional Model Builders Using 639 X-ray Structures
Sadowski, J., Gasteiger, J., & Klebe, G. (1994) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci00020a039 · Cited by 652 · see citing works
Ion Pairing in Transition-Metal Organometallic Chemistry
Macchioni, A. (2005) · Chemical Reviews · doi:10.1021/cr0300439 · Cited by 550 · see citing works
Automatic generation of 3D-atomic coordinates for organic molecules
Gasteiger, J., Rudolph, C., & Sadowski, J. (1990) · Tetrahedron Computer Methodology · doi:10.1016/0898-5529(90)90156-3 · Cited by 521 · see citing works
From atoms and bonds to three-dimensional atomic coordinates: automatic model builders
Sadowski, J., & Gasteiger, J. (1993) · Chemical Reviews · doi:10.1021/cr00023a012 · Cited by 414 · see citing works
Conformer Generation with OMEGA: Learning from the Data Set and the Analysis of Failures
Hawkins, P. C. D., & Nicholls, A. O. (2012) · Journal of Chemical Information and Modeling · doi:10.1021/ci300314k · Cited by 405 · see citing works
Towards a Universal SMILES representation - A standard method to generate canonical SMILES based on the InChI
O’Boyle, N. M. (2012) · Journal of Cheminformatics · doi:10.1186/1758-2946-4-22 · Cited by 363 · see citing works
Ethylene complexes. Bonding, rotational barriers, and conformational preferences
Albright, T. A., Hoffmann, R., Thibeault, J. C., et al. (1979) · Journal of the American Chemical Society · doi:10.1021/ja00508a017 · Cited by 301 · see citing works
Frog2: Efficient 3D conformation ensemble generator for small compounds
Miteva, M. A., Guyon, F., & Tufféry, P. (2010) · Nucleic Acids Research · doi:10.1093/nar/gkq325 · Cited by 288 · see citing works
Freely Available Conformer Generation Methods: How Good Are They?
Ebejer, J.-P., Morris, G. M., & Deane, C. M. (2012) · Journal of Chemical Information and Modeling · doi:10.1021/ci2004658 · Cited by 251 · see citing works
Analysis and Application of Potential Energy Smoothing and Search Methods for Global Optimization
Pappu, R. V., Hart, R. K., & Ponder, J. W. (1998) · The Journal of Physical Chemistry B · doi:10.1021/jp982255t · Cited by 249 · see citing works
DFT Studies of Alkene Insertions into Cu−B Bonds in Copper(I) Boryl Complexes
Dang, L., Zhao, H., Lin, Z., et al. (2007) · Organometallics · doi:10.1021/om070103r · Cited by 229 · see citing works
Nonbridged half-metallocenes containing anionic ancillary donor ligands: New promising candidates as catalysts for precise olefin polymerization
Nomura, K., Liu, J., Padmanabhan, S., et al. (2006) · Journal of Molecular Catalysis A Chemical · doi:10.1016/j.molcata.2006.11.006 · Cited by 217 · see citing works
Quantitative Structure−Activity Relationships of Ruthenium Catalysts for Olefin Metathesis
Occhipinti, G., Bjørsvik, H., & Jensen, V. R. (2006) · Journal of the American Chemical Society · doi:10.1021/ja060832i · Cited by 214 · see citing works
Self-citation
Rapidly Initiating Ruthenium Olefin‐Metathesis Catalysts
Romero, P. E., Piers, W. E., & McDonald, R. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200461374 · Cited by 196 · see citing works
Chemical Information in 3D Space
Gasteiger, J., Sadowski, J., Schuur, J., et al. (1996) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci960343+ · Cited by 196 · see citing works
Recent advances in olefin metathesis by molybdenum and tungsten imido alkylidene complexes
Schrock, R. R. (2004) · Journal of Molecular Catalysis A Chemical · doi:10.1016/j.molcata.2003.10.060 · Cited by 166 · see citing works
A computational study of phosphine ligand effects in Suzuki–Miyaura coupling☆
Jover, J., Fey, N., Purdie, M., et al. (2010) · Journal of Molecular Catalysis A Chemical · doi:10.1016/j.molcata.2010.02.021 · Cited by 162 · see citing works
Metal−Phosphine Bond Strengths of the Transition Metals: A Challenge for DFT
Minenkov, Y. V., Occhipinti, G., & Jensen, V. R. (2009) · The Journal of Physical Chemistry A · doi:10.1021/jp902940c · Cited by 132 · see citing works
Self-citation
Application of the diffusion equation method for global optimization to oligopeptides
Kostrowicki, J., & Scheraga, H. A. (1992) · The Journal of Physical Chemistry · doi:10.1021/j100197a057 · Cited by 128 · see citing works
The contribution of computational studies to organometallic catalysis: descriptors, mechanisms and models
Fey, N. (2009) · Dalton Transactions · doi:10.1039/b913356a · Cited by 125 · see citing works
Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates
Wenzel, A. G., & Grubbs, R. H. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0666598 · Cited by 124 · see citing works
The ligand field molecular mechanics model and the stereoelectronic effects of d and s electrons
Deeth, R. J. (2001) · Coordination Chemistry Reviews · doi:10.1016/s0010-8545(00)00354-4 · Cited by 120 · see citing works
Computational approaches for fragment-based and de novo design.
Loving, K., Alberts, I., & Sherman, W. (2010) · Current Topics in Medicinal Chemistry · doi:10.2174/156802610790232305 · Cited by 118 · see citing works
Computation of structures and properties of transition metal compounds
Comba, P., & Kerscher, M. (2008) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2008.05.019 · Cited by 111 · see citing works
Activity of Rhodium-Catalyzed Hydroformylation: Added Insight and Predictions from Theory
Sparta, M., Børve, K. J., & Jensen, V. R. (2007) · Journal of the American Chemical Society · doi:10.1021/ja070395n · Cited by 110 · see citing works
Self-citation
Predictive modeling in homogeneous catalysis: a tutorial
Maldonado, A. G., & Rothenberg, G. (2010) · Chemical Society Reviews · doi:10.1039/b921393g · Cited by 110 · see citing works
Frog: a FRee Online druG 3D conformation generator
Leite, T. B., Gomes, D. E. B., Miteva, M. A., et al. (2007) · Nucleic Acids Research · doi:10.1093/nar/gkm289 · Cited by 105 · see citing works
An Evolutionary Algorithm for de Novo Optimization of Functional Transition Metal Compounds
Chu, Y., Heyndrickx, W., Occhipinti, G., Jensen, V. R., & Alsberg, B. K. (2012) · Journal of the American Chemical Society · doi:10.1021/ja300865u · Cited by 90 · see citing works
Self-citation
De novo structure-based design of anion receptors
Hay, B. P. (2010) · Chemical Society Reviews · doi:10.1039/c0cs00075b · Cited by 89 · see citing works
HostDesigner: A Program for the de Novo Structure-Based Design of Molecular Receptors with Binding Sites that Complement Metal Ion Guests
Hay, B. P., & Firman, T. K. (2002) · Inorganic Chemistry · doi:10.1021/ic0202920 · Cited by 88 · see citing works
Subtle Balance of Ligand Steric Effects in Stille Transmetalation
Ariafard, A., & Yates, B. F. (2009) · Journal of the American Chemical Society · doi:10.1021/ja9007134 · Cited by 87 · see citing works
Differences in the Activation Processes of Phosphine-Containing and Grubbs–Hoveyda-Type Alkene Metathesis Catalysts
Núñez‐Zarur, F., Solans‐Monfort, X., Rodrı́guez-Santiago, L., et al. (2012) · Organometallics · doi:10.1021/om300150d · Cited by 87 · see citing works
Rotational barriers and conformations in transition metal complexes
Albright, T. A. (1982) · Accounts of Chemical Research · doi:10.1021/ar00077a004 · Cited by 84 · see citing works
DommiMOE: An implementation of ligand field molecular mechanics in the molecular operating environment
Deeth, R. J., Fey, N., & Williams-Hubbard, B. J. (2004) · Journal of Computational Chemistry · doi:10.1002/jcc.20137 · Cited by 84 · see citing works
Polyene-ML2 and -ML4 complexes. Conformational preferences and barriers of rotation
Albright, T. A., Hoffmann, R., Tse, Y.-C., et al. (1979) · Journal of the American Chemical Society · doi:10.1021/ja00508a018 · Cited by 76 · see citing works
In Silico Design in Homogeneous Catalysis Using Descriptor Modelling
Burello, E., & Rothenberg, G. (2006) · International Journal of Molecular Sciences · doi:10.3390/i7090375 · Cited by 75 · see citing works
Using CONCORD to construct a large database of three-dimensional coordinates from connection tables
Rusinko, A., Sheridan, R. P., Nilakantan, R., Haraki, K. S., Bauman, N., & Venkataraghavan, R. (1989) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci00064a004 · Cited by 73 · see citing works
Design and Assembly of Virtual Homogeneous Catalyst Libraries –Towards in silico Catalyst Optimisation
Hageman, J. A., Westerhuis, J. A., Frühauf, H., & Rothenberg, G. (2006) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200505299 · Cited by 61 · see citing works
Structure−Activity Correlation in Titanium Single-Site Olefin Polymerization Catalysts Containing Mixed Cyclopentadienyl/Aryloxide Ligation
Manz, T. A., Phomphrai, K., Medvedev, G. A., et al. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0640849 · Cited by 53 · see citing works
Automated Design of Realistic Organometallic Molecules from Fragments
Foscato, M., Occhipinti, G., Venkatraman, V., Alsberg, B. K., & Jensen, V. R. (2014) · Journal of Chemical Information and Modeling · doi:10.1021/ci4007497 · Cited by 49 · see citing works
Self-citation
An In Silico Design Tool for Fe(II) Spin Crossover and Light-Induced Excited Spin State-Trapped Complexes
Deeth, R. J., Anastasi, A. E., & Wilcockson, M. J. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1007323 · Cited by 46 · see citing works
Search for Improved Host Architectures: Application of de Novo Structure-Based Design and High-Throughput Screening Methods To Identify Optimal Building Blocks for Multidentate Ethers
Hay, B. P., Oliferenko, A. A., Uddin, J., et al. (2005) · Journal of the American Chemical Society · doi:10.1021/ja055169x · Cited by 46 · see citing works
Overcoming the Limitations of a Connection Table Description: A Universal Representation of Chemical Species
Bauerschmidt, S., & Gasteiger, J. (1997) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci9704423 · Cited by 45 · see citing works
DG-AMMOS: A New tool to generate 3D conformation of small molecules using D istance G eometry and A utomated M olecular M echanics O ptimization for in silico S creening
Lagorce, D., Pencheva, T., Villoutreix, B. O., et al. (2009) · BMC Chemical Biology · doi:10.1186/1472-6769-9-6 · Cited by 44 · see citing works
Ruthenium Alkylidene Complexes of Chelating Amine Ligands
Occhipinti, G., Bjørsvik, H., Törnroos, K. W., et al. (2007) · Organometallics · doi:10.1021/om070219n · Cited by 40 · see citing works
Self-citation
Synthesis, characterization and olefin metathesis studies of a family of ruthenium phosphonium alkylidene complexes
Dubberley, S. R., Romero, P. E., Piers, W. E., et al. (2005) · Inorganica Chimica Acta · doi:10.1016/j.ica.2005.09.040 · Cited by 36 · see citing works
Performance of the semiempirical PM3 (tm) method in the geometry optimization of transition metal complexes
Bosque, R., & Maseras, F. (2000) · Journal of Computational Chemistry · doi:10.1002/(sici)1096-987x(200005)21:7 · Cited by 35 · see citing works
Data-Driven High-Throughput Prediction of the 3-D Structure of Small Molecules: Review and Progress
Andronico, A., Randall, A. Z., Benz, R. W., & Baldi, P. (2011) · Journal of Chemical Information and Modeling · doi:10.1021/ci100223t · Cited by 31 · see citing works
Computational Tools for In Silico Fragment-Based Drug Design
Mortier, J., Rakers, C., Frédérick, R., & Wolber, G. (2012) · Current Topics in Medicinal Chemistry · doi:10.2174/156802612804547371 · Cited by 28 · see citing works
Can Semiempirical Quantum Mechanics Be Used To Predict the Spin State of Transition Metal Complexes? An Application of De Novo Prediction
Ball, D. M., Buda, C., Gillespie, A. M., et al. (2001) · Inorganic Chemistry · doi:10.1021/ic0108437 · Cited by 28 · see citing works
Quantitative Effects of Ion Pairing and Sterics on Chain Propagation Kinetics for 1-Hexene Polymerization Catalyzed by Mixed Cp′/ArO Complexes
Manz, T. A., Sharma, S., Phomphrai, K., et al. (2008) · Organometallics · doi:10.1021/om8004993 · Cited by 26 · see citing works
Conformational Energy Minimization Using a Two-Stage Method
Nakamura, S., Hirose, H., Ikeguchi, M., et al. (1995) · The Journal of Physical Chemistry · doi:10.1021/j100020a074 · Cited by 24 · see citing works
QSAR-modeling of toxicity of organometallic compounds by means of the balance of correlations for InChI-based optimal descriptors
Toropov, A. A., Toropova, A. P., & Benfenati, E. (2009) · Molecular Diversity · doi:10.1007/s11030-009-9156-6 · Cited by 23 · see citing works
Small-Molecule 3D Structure Prediction Using Open Crystallography Data
Sadowski, P., & Baldi, P. (2013) · Journal of Chemical Information and Modeling · doi:10.1021/ci4005282 · Cited by 22 · see citing works
Toward the computer-aided design of metal ion sequestering agents
Hay, B. P., Firman, T. K., Lumetta, G. J., et al. (2004) · Journal of Alloys and Compounds · doi:10.1016/j.jallcom.2003.11.049 · Cited by 21 · see citing works
Structure–Activity Correlation for Relative Chain Initiation to Propagation Rates in Single-Site Olefin Polymerization Catalysis
Manz, T. A., Caruthers, J. M., Sharma, S., et al. (2012) · Organometallics · doi:10.1021/om200884x · Cited by 21 · see citing works
Alkene rotation in [Ru(η5-C5H5) (L2) (η2-alkene][CF3SO3] with L2 = iPr- or pTol-diazabutadiene. X-ray crystal structure of [Ru(η5-C5H5(pTol-DAB) (η2-ethene][CF3SO3]
de Klerk‐Engels, B., Delis, J. G. P., Ernsting, J.-M., et al. (1995) · Inorganica Chimica Acta · doi:10.1016/0020-1693(95)04543-0 · Cited by 18 · see citing works
De NovoStructural Prediction of Transition Metal Complexes: Application to Technetium
Buda, C., Burt, S. K., Cundari, T. R., & Shenkin, P. S. (2002) · Inorganic Chemistry · doi:10.1021/ic0109748 · Cited by 16 · see citing works
QSPR modeling of enthalpies of formation for organometallic compounds by SMART‐based optimal descriptors
Toropov, A. A., Toropova, A. P., Benfenati, E., et al. (2009) · Journal of Computational Chemistry · doi:10.1002/jcc.21263 · Cited by 10 · see citing works
Three-dimensional structure generators of drug-like compounds: DG-AMMOS, an open-source package
Lagorce, D., Villoutreix, B. O., & Miteva, M. A. (2011) · Expert Opinion on Drug Discovery · doi:10.1517/17460441.2011.554393 · Cited by 9 · see citing works
De novo prediction of the ground state structure of transition metal complexes using semiempirical and ab initio quantum mechanics. Coordination isomerism
Buda, C., Flores, A., & Cundari, T. R. (2005) · Journal of Coordination Chemistry · doi:10.1080/00958970500038258 · Cited by 9 · see citing works
De novo prediction of ground state multiplicity and structural isomerism for transition metal complexes
Buda, C., & Cundari, T. R. (2004) · Journal of Molecular Structure THEOCHEM · doi:10.1016/j.theochem.2004.08.021 · Cited by 8 · see citing works
Starting Point to Molecular Design: Efficient Automated 3D Model Builder Key3D
Mizutani, M., Nakamura, K., Ichinose, T., et al. (2006) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.54.1680 · Cited by 8 · see citing works

Flagged first, then by citations

Sorted by citations

Computational Discovery of Transition-metal Complexes: From High-throughput Screening to Machine Learning
Nandy, A., Duan, C., Taylor, M. G., Liu, F., Steeves, A. H., & Kulik, H. J. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00347 · Cited by 358 · see citing works
Redox Control of Aluminum Ring-Opening Polymerization: A Combined Experimental and DFT Investigation
Wei, J., Riffel, M. N., & Diaconescu, P. L. (2017) · Macromolecules · doi:10.1021/acs.macromol.6b02402 · Cited by 76 · see citing works
Machine Learning for the Discovery, Design, and Engineering of Materials.
Duan, C., Nandy, A., & Kulik, H. J. (2022) · Annual Review of Chemical and Biomolecular Engineering · doi:10.1146/annurev-chembioeng-092320-120230 · Cited by 69 · see citing works
Leveraging Cheminformatics Strategies for Inorganic Discovery: Application to Redox Potential Design
Janet, J. P., Gani, T. Z. H., Steeves, A. H., Ioannidis, E. I., & Kulik, H. J. (2017) · Industrial & Engineering Chemistry Research · doi:10.1021/acs.iecr.7b00808 · Cited by 56 · see citing works
DENOPTIM: Software for Computational de Novo Design of Organic and Inorganic Molecules
Foscato, M., Venkatraman, V., & Jensen, V. R. (2019) · Journal of Chemical Information and Modeling · doi:10.1021/acs.jcim.9b00516 · Cited by 45 · see citing works
Self-citation
Ring Closure To Form Metal Chelates in 3D Fragment-Based de Novo Design
Foscato, M., Houghton, B. J., Occhipinti, G., Deeth, R. J., & Jensen, V. R. (2015) · Journal of Chemical Information and Modeling · doi:10.1021/acs.jcim.5b00424 · Cited by 21 · see citing works
Self-citation

Authors: Foscato, M., Venkatraman, V., Occhipinti, G., Alsberg, B. K., & Jensen, V. R.
Affiliations: University of Bergen (NO)
Norwegian University of Science and Technology (NO)
Corresponding author: Jensen, Vidar R.
ORCID: Foscato, Marco
Venkatraman, Vishwesh
Occhipinti, Giovanni
Jensen, Vidar R.
Venue: Journal of Chemical Information and Modeling
Publisher: American Chemical Society (ACS)
Published: 2014-07-16
Volume: 54
Issue: 7
Pages: 1919-1931
ISSN: 1549-9596 (ISSN-L)
1549-960X
DOI: 10.1021/ci5003153
OpenAlex: W1999992320
Cited by: 35
References: 72
Citations by year: 2026: 1 · 2025: 1 · 2024: 3 · 2023: 2 · 2022: 6 · 2021: 1 · 2020: 4 · 2019: 5 · 2018: 3 · 2017: 4 · 2016: 1 · 2015: 4
FWCI: 3.10
Type: journal article
Language: en
Open access: closed
Locations: Journal of Chemical Information and Modeling (publishedVersion)
PubMed (publishedVersion)
Funders: The Research Council of Norway (205273/V30, 208335/E30, NN2506K, NS2506K)
Topics: Physical Sciences › Computer Science › Computational Theory and Mathematics › Computational Drug Discovery Methods
Physical Sciences › Chemistry › Organic Chemistry › Organometallic Complex Synthesis and Catalysis
Physical Sciences › Physics and Astronomy › Atomic and Molecular Physics, and Optics › Advanced Chemical Physics Studies
Keywords: organometallic complexes, stereocontrol, molecular geometry, homogeneous catalysis
MeSH terms: Automation, Models, Molecular, Molecular Conformation, Organometallic Compounds, Quantum Theory, Crystallography, X-Ray

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Automated Building of Organometallic Complexes from 3D Fragments

Abstract

Integrity signals

Claims the paper makes

Cites

Cited by

Related

Record

About these checks