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Gabriel  dos Passos Gomes
Graduate Students

Gabriel dos Passos Gomes

Gabe received his B.Sc. in Chemistry from Federal University of Rio de Janeiro, Brazil under the supervision of Prof. Pierre Mothè Esteves, in 2013. His research at that university was focused on theoretical studies of electrophilic aromatic nitration via single electron transfer and a final project on theoretical/experimental development of methane clathrates inhibitors. He also spent a year at the University of Lisbon, Portugal in an academic exchange researching graphene oxides, with Professor Maria José Lourenço. In Fall 2014, he joined the laboratory of Professor Igor V. Alabugin at the Florida State University as a graduate student, where he also was awarded the LASER Fellowship earlier that year and the 2016-2017 IBM Ph.D Scholarship. His main interested is the interplay between structure and reactivity. For more, visit

Contact Information
Programs of Study
Research Website

Major Professor:
Dr. Igor Alabugin
Departmental Page
Dr. Igor Alabugin
Cottrell Family Professor

Research Interest

• Physical Organic Chemistry.
• Structure-Reactivity Relationships.
• Stereoelectronic effects.
• Cyclizations.
• Mechanisms of Organic Reactions.
• Computational Chemistry.
• Machine Learning.


(invited chapter): G. P. Gomes and I. V. Alabugin, Chapter 15: "Stereoelectronic Effects: Analysis by Computational and Theoretical Methods”, Applied Theoretical Organic Chemistry. Editor: Dean Tantillo, Wiley, March 2018 link
In print:
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”, 2018, just accepted, doi: 10.1021/acs.joc.8b00130
* = both authors contributed equally for this publication
23. N. P. Tsvetkov, E. Gonzalez-Rodriguez, A. Hughes, G. P. Gomes, F. D. White, I. V. Alabugin "Radical Alkyne Peri-annulations for Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene" Angew. Chem. Int. Ed., 2018, 57, 3651, doi: 10.1002/anie.201712651 (featured on FSU News and reproduced on:;; EurekAlert!)
22. V. A. Vil', G. P. Gomes, O. V. Bityukov, M. A. Syroeshkin, K. A. Lyssenko, G. I. Nikishin, I. V. Alabugin. A. O. Terent'ev "Interrupted Baeyer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate" Angew. Chem. Int. Ed., 2018, 2018, 57, 3372, doi: 10.1002/anie.201712651 (featured on Chemical & Engineering News)
21. K. N. Sedenkova, E. B. Averina, Y. K. Grishin, J. V. Kolodyazhnaya, V. B. Rybakov, T. S. Kuznetsova, A. Hughes, G. P. Gomes, I. V. Alabugin, N. S. Zefirov "Substituent effects on stereoselectivity of dihalocarbene reactions with cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in electrophilic nitrations on route to pyrimidine N-oxides" Org. Biom. Chem., 2017, 15, 9433 doi: 10.1039/C7OB02463K
20. C. J. Evoniuk, G. P. Gomes, S. Hill, F. Satoshi, K. Hanson, I. V. Alabugin "Coupling C-H activation with N-H deprotonation: metal-free C(sp3)-H aminations with unprotected anilines" J. Am. Chem. Soc., 2017, 139 (45), 16210 doi: 10.1021/jacs.7b07519
19. T. Harris, G. P. Gomes, S. Ayad, V. V. Lobodin, K. Hanson, I. V. Alabugin, "Twisted chiral cyclodecynes and remote activation of click reactivity" Chem, 2017, 3 (4), 629, doi: 10.1016/j.chempr.2017.07.011 video-summary of the paper ; This paper was featured on FSU News
18. N. H. Park, G. P. Gomes, M. Fevre, G. O. Jones, I. V. Alabugin, J. L. Hedrick "Organocatalyzed Synthesis of Fluorinated Poly(aryl thioethers)" Nature Communications, 2017, 8, 166 doi: 10.1038/s41467-017-00186-3; erratum for Fig.2: a collaboration with IBM Research, CA (This paper was featured on Plastic News and on Synfacts 2017, 13 (10), 1035 “Salt-Free Polymerization Yields Fluorinated Poly(aryl thioether)s”, doi: 10.1055/s-0036-1591247
17. E. Juaristi, G. P. Gomes, A. O. Terent’ev, R. Notario, I. V. Alabugin "Stereoelectronic Interactions as a Probe for the Existence of the Intramolecular α-Effect", J. Am. Chem. Soc., 2017, 139 (9), 3406, doi: 10.1021/jacs.7b05367
16. P. Poonptana, G. P. Gomes, T. Hurrle, K. Chardon, S. Bräse, K-S. Masters, I. V. Alabugin "Formaldehyde-Extruding Homolytic Aromatic Substitution via C->O Transposition: Evolution of a Contaminating Side-Reaction to ‘Traceless-Linker’ access to Congested Biaryl Bonds" Chem. Eur. J., 2017, 23, 9091 doi: 10.1002/chem.201700085 (Hot Paper on Chemistry – A European Journal)
15. G. P. Gomes*, C. J. Evoniuk*, M. Ly, I. V. Alabugin "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. Biom. Chem., 2017, 15, 4135 doi: 10.1039/C7OB00527J
14. C. J. Evoniuk*, G. P. Gomes*, M. Ly, F. D. White, I. V. Alabugin "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 doi: 10.1021/acs.joc.7b00262(featured on Synfacts 2017, 13 (06), 253 “Synthesis of Quinolines From o-Alkenylaryl Isonitriles”, doi: 10.1055/s-0036-1590439 and on
13. G. P. Gomes*, Y. A. Yaremenko*, P. S. Radulov, R. A. Novikov, V. V. Chernyshev, A. A. Korlyukov, G. I. Nikishin, A. O. Terent’ev, I. V. Alabugin "Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides " Angew. Chem. Int. Ed., 2017, 56, 4955 doi: 10.1002/anie.201610699
12. G. P. Gomes & I. V. Alabugin "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 doi: 10.1021/jacs.6b11054
11. S. Umedu, G. P. Gomes, M. Sakae, T. Yoshinaga, K. Matsumoto, T. Iwata, I. V. Alabugin, M. Shindo "Regioselective One-pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates" Angew. Chem. Int. Ed., 2016, 56, 1298 doi: 10.1002/anie.201609111 (featured on Synfacts 2017, 13 (03), 253 “Three Benzynes and the Ynolate”, doi: 10.1055/s-0036-1590046)
10. S. Z. Vatsadze, Y. D. Loginova, G. P. Gomes, I. V. Alabugin, "Stereoelectronic Chameleons: The Donor–Acceptor Dichotomy of Functional Groups" Chem. Eur. J., 2016, 23, 3225 doi: 10.1002/chem.201603491 (Frontspiece of Chemistry – A European Journal, doi: 10.1002/chem.2017814611
9. K. Pati, G. P. Gomes, I. V. Alabugin, "Combining Traceless Directing Groups with Hybridization Control of Radical Reactivity: From Skipped Enynes to Defect-Free Hexagonal Frameworks" Angew. Chem. Int. Ed., 2016, 128, 11805 doi: 10.1002/ange.201605799
8. T. Harris, G. P. Gomes, R. Clark, I. V. Alabugin, "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 doi: 10.1021/acs.joc.6b01052 This paper was featured on
7. E. Berry*, G. P. Gomes*, A. MacLean, J. R. Martin, P. A. Wiget, "Discovery of a new type of Perlin effect in a conformationally constrained oxocane" J. Org. Chem., 2016, 81 (13), 5740 doi: 10.1021/acs.joc.6b00819
6. K. Pati, G. P. Gomes, T. Harris, I. V. Alabugin "Fused Catechol Ethers from Gold (I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals" Org. Lett., 2016, doi: 10.1021/acs.orglett.5b03522
5. G. P. Gomes, V. A. Vil’, A. Terent’ev and I. Alabugin, "Stereoelectronic source of the anomalous stability of bis- peroxides", Chem. Sci., 2015, doi: 10.1039/C5SC02402A. This paper was featured on RSC's Chemistry World and on NBO's features website.
4. K. Pati, C. Michas, D. Allenger, I. Piskun, P. Spiro Coutros, G. P. Gomes, I. V Alabugin "Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization." J. Org. Chem., 2015, doi: 10.1021/acs.joc.5b01014
3. E. Stoyanov and G. P. Gomes "Tert-Butyl Carbocation in Condensed Phases: Stabilization via Hyperconjugation, Polarization and Hydrogen Bonding.” J. Phys. Chem. A, 2015 doi: 10.1021/acs.jpca.5b04657
2. K. Pati, G. P. Gomes, T. Harris, A. Hughes, H. Phan, T. Banerjee, K. Hanson, Igor V. Alabugin "Traceless Directing Groups in Radical Cascades: From Oligoalkynes to Fused Helicenes without Tethered Initiators" J. Am. Chem. Soc., 2014; doi: 10.1021/ja510563d
1. Alabugin, I. V., Bresch S., Gomes, G. P., J. Phys. Org. Chem., 2014, "Orbital Hybridization: a Key Electronic Factor in Control of Structure and Reactivity"; doi: 10.1002/poc.3382. This paper was featured on