Publications

Preprints

(34) P. Friederich, G. P. Gomes, R. D. Bin, A. Aspuru-Guzik, D. Balcells “Machine Learning Chemical Reactivity Surrounding Vaska’s Complexes Chemical Space”, submitted, 2019

• Preprint on ChemRxiv: link to ChemRxiv_v1

• GitHub page: link to GitHub page • DataVerse page: link to DataVerse page

(33) Q. Elliott, G. P. Gomes, C. J. Evoniuk, I. V. Alabugin “Diverting Radical-Anionic C-H Amination to a C-N/C-O Cascade for the Construction of Hydroxyisoindolines from Unprotected Amides”, submitted, 2019

Preprint on ChemRxiv: link to ChemRxiv_v1

Published

^‡ = both authors contributed equally for this publication

(32) R. Lee, E. Cagle, B. Bashrum, E. Walters, J. Massey, M. Zanghi, C. Birchfield, D. French, J. Joy, G. P. Gomes, P. A. Wiget “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), 9867, doi: 10.1021/acs.joc.9b00979

(31) G. P. Gomes, A. Wimmer, J. Smith, B. König, I. V. Alabugin “CO₂ or SO₂: Should it stay, or should it go?”, J. Org. Chem., 2019, 84 (10), 6232, doi: 10.1021/acs.joc.9b00503

Preprint on ChemRxiv: link to ChemRxiv_v2

(30) A. Hughes, G. P. Gomes, I. V. Alabugin “Stereoelectronic Influence of a “Spectator” Propargylic Substituent Can Override Aromaticity Effects in Radical Peri-cyclizations on Route to Expanded Polyaromatics”, J. Org. Chem., 2019, 84 (4), 1853, doi: 10.1021/acs.joc.8b02779

(29) G. P. Gomes, A. E. Morrison, G. B. Dudley, I. V. Alabugin, “Optimizing amine-mediated alkyne-allene isomerization to improve benzannulation cascades: synergy between theory and experiments”, Eur. J. Org. Chem., 2019, 512, Special Issue: Catalyst Design, doi.org/10.1002/ejoc.201801052

(28) V. A. Vil’, G. P. Gomes, M. V. Ekimova, K. A. Lyssenko, G. I. Nikishin, I. V. Alabugin, A. O. Terent’ev “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, doi: 10.1021/acs.joc.8b02218

(27) G. P. Gomes, Y. D. Loginova, S. Z. Vatsadze, I. V. Alabugin, “Isonitriles as Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy in Radical Additions”, J. Am. Chem. Soc., 2018, 140 (43), 14272, doi: 10.1021/jacs.8b08513

(Highlighted on: • ACS Axial; • Colorblind Chemist) Preprint on ChemRxiv: link to ChemRxiv_v1

(26) I. V. Alabugin, G. P. Gomes, M. Abdo, “Hyperconjugation”, WIREs Comput. Mol. Sci., 2018;e1389, doi.org/10.1002/wcms.1389

( • Featured as one of the top 20 most downloaded papers in WIREs Comput. Mol. Sci. in the first 12 months following its publication.)

(25) 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, pp. 451–502, May, 2018, doi:10.1142/9781786344090_0015 link

(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, doi: 10.1021/acs.joc.8b00130

(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.201712783

Featured on FSU News and reproduced on: phys.org; sciencedaily.com; 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, 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; Fig.2: here a collaboration with IBM Research, CA

(This paper was featured on: • Plastic News; • Synfacts 2017, 13 (10), 1035 “Salt-Free Polymerization Yields Fluorinated Poly(aryl thioether)s”, doi: 10.1055/s-0036-1591247; • IBM Research Blog, “New discovery: Rapid preparation of high performance materials and coatings”

(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

Featured as 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; • on organic-chemistry.org

(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

(Web of Science’s top 1% Chemistry highly cited papers for Nov/Dec 2017; Frontspiece of Chemistry – A European Journal, doi: 10.1002/chem.201781461

(09) 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

(08) 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 sciencing.net

(07) 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

(06) 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, 18 (5), 928, doi: 10.1021/acs.orglett.5b03522

(05) G. P. Gomes, V. A. Vil’, A. Terent’ev and I. Alabugin, “Stereoelectronic source of the anomalous stability of bis- peroxides”, Chem. Sci., 2015, 6, 6783, doi: 10.1039/C5SC02402A.

This paper was featured on: • RSC’s Chemistry World; • on NBO’s features website. Behind the scenes on: medium.com.

(04) 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, 80 (23), 11706, doi: 10.1021/acs.joc.5b01014

(03) E. Stoyanov and G. P. Gomes “Tert-Butyl Carbocation in Condensed Phases: Stabilization via Hyperconjugation, Polarization and Hydrogen Bonding.” J. Phys. Chem. A, 2015, 119, 8619, doi: 10.1021/acs.jpca.5b04657

(02) 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, 137, 1165; doi: 10.1021/ja510563d

(01) Alabugin, I. V., Bresch S., Gomes, G. P., “Orbital Hybridization: a Key Electronic Factor in Control of Structure and Reactivity”, J. Phys. Org. Chem., 2014, 28, 147, doi: 10.1002/poc.3382.

This paper was featured on amphoteros.com

PhD dissertation

G. P. Gomes “Controlling chemical reactivity with stereoelectronic effects.” Ann Arbor: The Florida State University; 2018. 326 p. link