Krenn, M.; Pollice, R.; Guo, S. Y.; Aldeghi, M.; Cervera-Lierta, A.; Friederich, P.; Gomes, G. dos P.; Häse, F.; Jinich, A.; Nigam, A.; Yao, Z.; Aspuru-Guzik, A.
On Scientific Understanding with Artificial Intelligence.
arXiv
2022.
https://doi.org/10.48550/ARXIV.2204.01467.
47. Gensch, T.; Gomes, G. dos P.; Friederich,
P.; Peters, E.; Gaudin, T.; Pollice, R.; Jorner, K.; Nigam, A.; D’Addario, M. L.; Sigman, M. S.;
Aspuru-Guzik, A. A Comprehensive Discovery Platform for Organophosphorus Ligands for Catalysis.
J. Am. Chem. Soc. 2022 https://doi.org/10.1021/jacs.1c09718.
46. Christensen, M.; Yunker, L.; Adedeji, F.;
Häse, F.; Roch, L.; Gensch, T.; Gomes, G. dos P.; Zepel, T.; Sigman, M.; Aspuru-Guzik, A.; Hein, J.
Data-Science Driven Autonomous Process Optimization.
2020.
https://doi.org/10.26434/chemrxiv.13146404.v2.
45. Nigam, A.; Pollice, R.; Krenn, M.; Gomes,
G. dos P.; Aspuru-Guzik, A. Beyond Generative Models: Superfast Traversal, Optimization, Novelty,
Exploration and Discovery (STONED) Algorithm for Molecules Using SELFIES.
2021.
https://doi.org/10.26434/chemrxiv.13383266.v2.
44. Auhim, H. S.; Grigorenko, B. L.; Harris,
T. K.; Aksakal, O. E.; Polyakov, I. V.; Berry, C.; Gomes, G. dos P.; Alabugin, I. V.; Rizkallah, P.
J.; Nemukhin, A. V.; Jones, D. D. Stalling Chromophore Synthesis of the Fluorescent Protein Venus
Reveals the Molecular Basis of the Final Oxidation Step.
Chem. Sci. 2021,
12
(22), 7735–7745.
https://doi.org/10.1039/D0SC06693A.
43. R. Pollice, P. Friederich, C. Lavigne, G. P. Gomes, A. Aspuru-Guzik Organic Molecules with Inverted Gaps between
First Excited Singlet and Triplet States and Appreciable Oscillator Strengths, Matter
2021 4 (5), 1654.
https://doi.org/10.26434/chemrxiv.13087319.
42. dos Passos Gomes, G.; Xu, G.; Zhu, X.;
Chamoreau, L.-M.; Zhang, Y.; Bistri-Aslanoff, O.; Roland, S.; Alabugin, I. V.; Sollogoub, M. Mapping
C−H⋅⋅⋅M Interactions in Confined Spaces: (α-ICyDMe)Au, Ag, Cu Complexes Reveal “Contra-Electrostatic
H Bonds” Masquerading as Anagostic Interactions**.
Chemistry – A European Journal
2021,
27 (31), 8127–8142.
https://doi.org/10.1002/chem.202100263.
41. Diaz, D. B.; Appavoo, S. D.;
Bogdanchikova, A. F.; Lebedev, Y.; McTiernan, T. J.; dos Passos Gomes, G.; Yudin, A. K. Illuminating
the Dark Conformational Space of Macrocycles Using Dominant Rotors.
Nat. Chem. 2021,
13 (3), 218–225.
https://doi.org/10.1038/s41557-020-00620-y.
40. Pollice, R.; dos Passos Gomes, G.;
Aldeghi, M.; Hickman, R. J.; Krenn, M.; Lavigne, C.; Lindner-D’Addario, M.; Nigam, A.; Ser, C. T.;
Yao, Z.; Aspuru-Guzik, A. Data-Driven Strategies for Accelerated Materials Design.
Acc. Chem.
Res. 2021,
54 (4), 849–860.
https://doi.org/10.1021/acs.accounts.0c00785.
38. Kaldas, S. J.; Tien, C.-H.; Gomes, G. dos
P.; Meyer, S.; Sirvinskas, M.; Foy, H.; Dudding, T.; Yudin, A. K. Oxidative Rearrangement of MIDA
(N-Methyliminodiacetic Acid) Boronates: Mechanistic Insights and Synthetic Applications.
Org.
Lett. 2021,
23 (2), 324–328.
https://doi.org/10.1021/acs.orglett.0c03823.
37. S. C. Davidson, G. P. Gomes, L. R. Kuhn, I. V. Alabugin, A. R. Kennedy, N. C. O. Tomkinson “Organocatalytic
sulfoxidation”, Tetrahedron,
2021, 78, 131784, ISSN 0040-4020.
https://doi.org/10.1016/j.tet.2020.131784.
36. Mills, L. R.; Monteith, J. J.; dos Passos
Gomes, G.; Aspuru-Guzik, A.; Rousseaux, S. A. L. The Cyclopropane Ring as a Reporter of Radical
Leaving-Group Reactivity for Ni-Catalyzed C(Sp3)–O Arylation.
J. Am. Chem. Soc. 2020,
142 (30), 13246–13254.
https://doi.org/10.1021/jacs.0c06904.
35. Friederich, P.; Gomes, G. dos P.; Bin, R.
D.; Aspuru-Guzik, A.; Balcells, D. Machine Learning Dihydrogen Activation in the Chemical Space
Surrounding Vaska’s Complex.
Chem. Sci. 2020,
11 (18), 4584–4601.
https://doi.org/10.1039/D0SC00445F.
34. Gonzalez-Rodriguez, E.; Abdo, M. A.; dos
Passos Gomes, G.; Ayad, S.; White, F. D.; Tsvetkov, N. P.; Hanson, K.; Alabugin, I. V. Twofold
π-Extension of Polyarenes via Double and Triple Radical Alkyne Peri-Annulations: Radical Cascades
Converging on the Same Aromatic Core.
J. Am. Chem. Soc. 2020,
142 (18),
8352–8366.
https://doi.org/10.1021/jacs.0c01856.
33. Elliott, Q.; Gomes, G. dos P.; Evoniuk, C.
J.; Alabugin, I. V. Testing the Limits of Radical-Anionic CH-Amination: A 10-Million-Fold Decrease
in Basicity Opens a New Path to Hydroxyisoindolines via a Mixed C–N/C–O-Forming Cascade.
Chem.
Sci. 2020,
11 (25), 6539–6555.
https://doi.org/10.1039/C9SC06511C.
32. Lee, R.; Bashrum, B.; Cagle, E. C.;
Walters, J.; Massey, J.; Zanghi, M.; Birchfield, C.; French, D.; Joy, J.; dos Passos Gomes, G.;
Wiget, P. A. Electronic Donation or Steric Contraction: A Spectroscopic and Structural Analysis of
Medium-Sized Constrained Rings for Potential Long-Range Hyperconjugation.
J. Org. Chem.
2019,
84 (16), 9897–9906.
https://doi.org/10.1021/acs.joc.9b00979.
31. dos Passos Gomes, G.; Wimmer, A.; Smith,
J. M.; König, B.; Alabugin, I. V. CO
2 or SO
2: Should It Stay, or Should It Go?
J. Org. Chem.
2019,
84 (10), 6232–6243.
https://doi.org/10.1021/acs.joc.9b00503.
30. Hughes, A. M.; dos Passos Gomes, G.;
Alabugin, I. V. Stereoelectronic Influence of a “Spectator” Propargylic Substituent Can Override
Aromaticity Effects in Radical Peri-Cyclizations En Route to Expanded Polyaromatics.
J. Org.
Chem. 2019,
84 (4), 1853–1862.
https://doi.org/10.1021/acs.joc.8b02779.
29. dos Passos Gomes, G.; Morrison, A. E.;
Dudley, G. B.; Alabugin, I. V. Optimizing Amine-Mediated Alkyne–Allene Isomerization to Improve
Benzannulation Cascades: Synergy between Theory and Experiments.
European Journal of Organic
Chemistry 2019,
2019 (2–3), 512–518.
https://doi.org/10.1002/ejoc.201801052.
28. Vil’, V. A.; Gomes, G. dos P.; Ekimova, M.
V.; Lyssenko, K. A.; Syroeshkin, M. A.; Nikishin, G. I.; Alabugin, I. V.; Terent’ev, A. O. Five
Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of
β-Hydroperoxy-β-Peroxylactones.
J. Org. Chem. 2018,
83 (21), 13427–13445.
https://doi.org/10.1021/acs.joc.8b02218.
27. Gomes, G. dos P.; Loginova, Y.; Vatsadze,
S. Z.; Alabugin, I. V. Isocyanides as Stereoelectronic Chameleons: The Donor–Acceptor Dichotomy in
Radical Additions.
J. Am. Chem. Soc. 2018,
140 (43), 14272–14288.
https://doi.org/10.1021/jacs.8b08513.
26. Alabugin, I. V.; dos Passos Gomes, G.;
Abdo, M. A. Hyperconjugation.
WIREs Computational Molecular Science 2019,
9
(2), e1389.
https://doi.org/10.1002/wcms.1389.
25. G. P. Gomes & I. V. Alabugin. Stereoelectronic Effects: Analysis by Computational and Theoretical Methods, chapter 15 for the book
“Applied Theoretical Organic Chemistry”, pp. 451-502,
2018, Ed: Dean Tantillo
https://doi.org/10.1021/jacs.8b08513.
24. Y. A. Yaremenko, G. P. Gomes, P. S. Radulov, R. A. Novikov, V. V. Chernyshev, A. A. Korlyukov, G. I. Nikishin, I. V.
Alabugin, A. O. Terent’ev. Ozone-free synthesis of ozonides: Assembling bicyclic structures from 1,5-diketones and
hydrogen peroxide
J. Org. Chem., 2018,
83 (8), 4402.
https://doi.org/10.1021/acs.joc.8b00130.
23. Tsvetkov, N. P.; Gonzalez-Rodriguez, E.;
Hughes, A.; dos Passos Gomes, G.; White, F. D.; Kuriakose, F.; Alabugin, I. V. Radical Alkyne
Peri-Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and
Olympicene.
Angewandte Chemie International Edition 2018,
57 (14), 3651–3655.
https://doi.org/10.1002/anie.201712783.
22. Vil’, V. A.; dos Passos Gomes, G.;
Bityukov, O. V.; Lyssenko, K. A.; Nikishin, G. I.; Alabugin, I. V.; Terent’ev, A. O. Interrupted
Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate.
Angewandte Chemie International Edition 2018,
57 (13), 3372–3376.
https://doi.org/10.1002/anie.201712651.
21. Sedenkova, K. N.; Averina, E. B.; Grishin,
Y. K.; Kolodyazhnaya, J. V.; Rybakov, V. B.; Kuznetsova, T. S.; Hughes, A.; Gomes, G. dos P.;
Alabugin, I. V.; Zefirov, N. S. Substituent Effects on Stereoselectivity of Dihalocarbene Reactions
with Cyclohexadiene and on the Reactivity of Bis-Dihalocyclopropanes in Electrophilic Nitrations En
Route to Pyrimidine N-Oxides.
Org. Biomol. Chem. 2017,
15 (44), 9433–9441.
https://doi.org/10.1039/C7OB02463K.
20. Evoniuk, C. J.; Gomes, G. dos P.; Hill, S.
P.; Fujita, S.; Hanson, K.; Alabugin, I. V. Coupling N–H Deprotonation, C–H Activation, and
Oxidation: Metal-Free C(Sp3)–H Aminations with Unprotected Anilines.
J. Am. Chem. Soc.
2017,
139 (45), 16210–16221.
https://doi.org/10.1021/jacs.7b07519.
19. Harris, T.; Gomes, G. dos P.; Ayad, S.;
Clark, R. J.; Lobodin, V. V.; Tuscan, M.; Hanson, K.; Alabugin, I. V. Twisted Cycloalkynes and
Remote Activation of “Click” Reactivity.
Chem 2017,
3 (4), 629–640.
https://doi.org/10.1016/j.chempr.2017.07.011.
18. Park, N. H.; Gomes, G. dos P.; Fevre, M.;
Jones, G. O.; Alabugin, I. V.; Hedrick, J. L. Organocatalyzed Synthesis of Fluorinated Poly(Aryl
Thioethers).
Nat Commun 2017,
8 (1), 166.
https://doi.org/10.1038/s41467-017-00186-3.
17. Juaristi, E.; dos Passos Gomes, G.;
Terent’ev, A. O.; Notario, R.; Alabugin, I. V. Stereoelectronic Interactions as a Probe for the
Existence of the Intramolecular α-Effect.
J. Am. Chem. Soc. 2017,
139 (31),
10799–10813.
https://doi.org/10.1021/jacs.7b05367.
16. Poonpatana, P.; Gomes, G. dos P.; Hurrle,
T.; Chardon, K.; Bräse, S.; Masters, K.-S.; Alabugin, I. Formaldehyde-Extruding Homolytic Aromatic
Substitution via C→O Transposition: Selective ‘Traceless-Linker’ Access to Congested Biaryl Bonds.
Chemistry – A European Journal 2017,
23 (38), 9091–9097.
https://doi.org/10.1002/chem.201700085.
15. Gomes, G. dos P.; Evoniuk, C. J.; Ly, M.;
Alabugin, I. V. Changing the Path of Least Resistance, or Access to Endo-Dig Products via a Sequence
of Three Exo-Trig Transition States: Electronic Effects in Homoallyic Ring Expansion Cascades of
Alkenyl Isonitriles.
Org. Biomol. Chem. 2017,
15 (19), 4135–4143.
https://doi.org/10.1039/C7OB00527J.
14. Evoniuk, C. J.; Gomes, G. dos P.; Ly, M.;
White, F. D.; Alabugin, I. V. Coupling Radical Homoallylic Expansions with C–C Fragmentations for
the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl,
Alkyl, and Perfluoroalkyl Radicals.
J. Org. Chem. 2017,
82 (8), 4265–4278.
https://doi.org/10.1021/acs.joc.7b00262.
13. dos Passos Gomes, G.; Yaremenko, I. A.;
Radulov, P. S.; Novikov, R. A.; Chernyshev, V. V.; Korlyukov, A. A.; Nikishin, G. I.; Alabugin, I.
V.; Terent’ev, A. O. Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides.
Angewandte
Chemie International Edition 2017,
56 (18), 4955–4959.
https://doi.org/10.1002/anie.201610699.
12. dos Passos Gomes, G.; Alabugin, I. V.
Drawing Catalytic Power from Charge Separation: Stereoelectronic and Zwitterionic Assistance in the
Au(I)-Catalyzed Bergman Cyclization.
J. Am. Chem. Soc. 2017,
139 (9),
3406–3416.
https://doi.org/10.1021/jacs.6b11054.
11. Umezu, S.; dos Passos Gomes, G.;
Yoshinaga, T.; Sakae, M.; Matsumoto, K.; Iwata, T.; Alabugin, I.; Shindo, M. Regioselective One-Pot
Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.
Angewandte Chemie
International Edition 2017,
56 (5), 1298–1302.
https://doi.org/10.1002/anie.201609111.
10. Vatsadze, S. Z.; Loginova, Y. D.; dos
Passos Gomes, G.; Alabugin, I. V. Stereoelectronic Chameleons: The Donor–Acceptor Dichotomy of
Functional Groups.
Chemistry – A European Journal 2017,
23 (14), 3225–3245.
https://doi.org/10.1002/chem.201603491.
9. Pati, K.; dos Passos Gomes, G.; Alabugin,
I. V. Combining Traceless Directing Groups with Hybridization Control of Radical Reactivity: From
Skipped Enynes to Defect-Free Hexagonal Frameworks.
Angewandte Chemie 2016,
128
(38), 11805–11809.
https://doi.org/10.1002/ange.201605799.
8. Harris, T.; Gomes, G. dos P.; Clark, R.
J.; Alabugin, I. V. Domino Fragmentations in Traceless Directing Groups of Radical Cascades:
Evidence for the Formation of Alkoxy Radicals via C–O Scission.
J. Org. Chem. 2016,
81 (14), 6007–6017.
https://doi.org/10.1021/acs.joc.6b01052.
7. Berry, E.; Gomes, G. dos P.; MacLean, A.;
Martin, J. R.; Wiget, P. A. Discovery of a Long-Range Perlin Effect in a Conformationally
Constrained Oxocane.
J. Org. Chem. 2016,
81 (13), 5740–5744.
https://doi.org/10.1021/acs.joc.6b00819.
6. Pati, K.; Gomes, G. dos P.; Harris, T.;
Alabugin, I. V. Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl
Ethers with Acetals.
Org. Lett. 2016,
18 (5), 928–931.
https://doi.org/10.1021/acs.orglett.5b03522.
5. Gomes, G. dos P.; Vil’, V.; Terent’ev, A.;
Alabugin, I. V. Stereoelectronic Source of the Anomalous Stability of Bis-Peroxides.
Chem.
Sci. 2015,
6 (12), 6783–6791.
https://doi.org/10.1039/C5SC02402A.
4. Pati, K.; Michas, C.; Allenger, D.;
Piskun, I.; Coutros, P. S.; Gomes, G. dos P.; Alabugin, I. V. Synthesis of Functionalized
Phenanthrenes via Regioselective Oxidative Radical Cyclization.
J. Org. Chem. 2015,
80 (23), 11706–11717.
https://doi.org/10.1021/acs.joc.5b01014.
3. Stoyanov, E. S.; Gomes, G. dos P.
tert-Butyl Carbocation in Condensed Phases: Stabilization via Hyperconjugation, Polarization, and
Hydrogen Bonding The Journal of Physical Chemistry A
2015 119 (32), 8619-8629
https://doi.org/10.1021/acs.jpca.5b04657.
2. Pati, K.; Gomes, G. dos P.; Harris, T.;
Hughes, A.; Phan, H.; Banerjee, T.; Hanson, K.; Alabugin, I. V. Traceless Directing Groups in
Radical Cascades: From Oligoalkynes to Fused Helicenes without Tethered Initiators Journal of the American Chemical Society
2015 137 (3), 1165-1180
https://doi.org/10.1021/ja510563d.
1. Alabugin, I. V.; Bresch, S.; Gomes, G. dos
P. Orbital Hybridization: A Key Electronic Factor in Control of Structure and Reactivity.
Journal
of Physical Organic Chemistry 2015,
28 (2), 147–162.
https://doi.org/10.1002/poc.3382.
1. Gomes, G. dos P.; Alabugin, I.
Stereoelectronic Effects: Analysis by Computational and Theoretical Methods. In
Applied
Theoretical Organic Chemistry; WORLD SCIENTIFIC (EUROPE), 2017; pp 451–502.
https://doi.org/10.1142/9781786344090_0015.