[{"article_processing_charge":"No","publisher":"American Chemical Society","extern":"1","pmid":1,"doi":"10.1021/acs.joc.2c02381","oa":1,"volume":88,"author":[{"first_name":"Tomer","last_name":"Weiss","full_name":"Weiss, Tomer"},{"first_name":"Alexandra","full_name":"Wahab, Alexandra","last_name":"Wahab"},{"orcid":"0000-0001-9699-8730","id":"58f3726e-7cba-11ef-ad8b-e6e8cb3904e6","first_name":"Alexander","last_name":"Bronstein","full_name":"Bronstein, Alexander"},{"first_name":"Renana","full_name":"Gershoni-Poranne, Renana","last_name":"Gershoni-Poranne"}],"month":"01","article_type":"original","publication_identifier":{"issn":["0022-3263"],"eissn":["1520-6904"]},"date_created":"2024-10-08T12:47:17Z","title":"Interpretable deep-learning unveils structure–property relationships in polybenzenoid hydrocarbons","oa_version":"Preprint","publication_status":"published","status":"public","page":"9645-9656","issue":"14","scopus_import":"1","publication":"The Journal of Organic Chemistry","date_updated":"2024-10-09T10:49:42Z","intvolume":"        88","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","year":"2023","date_published":"2023-01-25T00:00:00Z","main_file_link":[{"open_access":"1","url":"10.26434/chemrxiv-2022-krng1"}],"external_id":{"pmid":["36696660"]},"_id":"18209","language":[{"iso":"eng"}],"abstract":[{"lang":"eng","text":"In this work, interpretable deep learning was used to identify structure–property relationships governing the HOMO–LUMO gap and the relative stability of polybenzenoid hydrocarbons (PBHs) using a ring-based graph representation. This representation was combined with a subunit-based perception of PBHs, allowing chemical insights to be presented in terms of intuitive and simple structural motifs. The resulting insights agree with conventional organic chemistry knowledge and electronic structure-based analyses and also reveal new behaviors and identify influential structural motifs. In particular, we evaluated and compared the effects of linear, angular, and branching motifs on these two molecular properties and explored the role of dispersion in mitigating the torsional strain inherent in nonplanar PBHs. Hence, the observed regularities and the proposed analysis contribute to a deeper understanding of the behavior of PBHs and form the foundation for design strategies for new functional PBHs."}],"quality_controlled":"1","type":"journal_article","day":"25","citation":{"ama":"Weiss T, Wahab A, Bronstein AM, Gershoni-Poranne R. Interpretable deep-learning unveils structure–property relationships in polybenzenoid hydrocarbons. <i>The Journal of Organic Chemistry</i>. 2023;88(14):9645-9656. doi:<a href=\"https://doi.org/10.1021/acs.joc.2c02381\">10.1021/acs.joc.2c02381</a>","ista":"Weiss T, Wahab A, Bronstein AM, Gershoni-Poranne R. 2023. Interpretable deep-learning unveils structure–property relationships in polybenzenoid hydrocarbons. The Journal of Organic Chemistry. 88(14), 9645–9656.","chicago":"Weiss, Tomer, Alexandra Wahab, Alex M. Bronstein, and Renana Gershoni-Poranne. “Interpretable Deep-Learning Unveils Structure–Property Relationships in Polybenzenoid Hydrocarbons.” <i>The Journal of Organic Chemistry</i>. American Chemical Society, 2023. <a href=\"https://doi.org/10.1021/acs.joc.2c02381\">https://doi.org/10.1021/acs.joc.2c02381</a>.","mla":"Weiss, Tomer, et al. “Interpretable Deep-Learning Unveils Structure–Property Relationships in Polybenzenoid Hydrocarbons.” <i>The Journal of Organic Chemistry</i>, vol. 88, no. 14, American Chemical Society, 2023, pp. 9645–56, doi:<a href=\"https://doi.org/10.1021/acs.joc.2c02381\">10.1021/acs.joc.2c02381</a>.","ieee":"T. Weiss, A. Wahab, A. M. Bronstein, and R. Gershoni-Poranne, “Interpretable deep-learning unveils structure–property relationships in polybenzenoid hydrocarbons,” <i>The Journal of Organic Chemistry</i>, vol. 88, no. 14. American Chemical Society, pp. 9645–9656, 2023.","short":"T. Weiss, A. Wahab, A.M. Bronstein, R. Gershoni-Poranne, The Journal of Organic Chemistry 88 (2023) 9645–9656.","apa":"Weiss, T., Wahab, A., Bronstein, A. M., &#38; Gershoni-Poranne, R. (2023). Interpretable deep-learning unveils structure–property relationships in polybenzenoid hydrocarbons. <i>The Journal of Organic Chemistry</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acs.joc.2c02381\">https://doi.org/10.1021/acs.joc.2c02381</a>"}},{"citation":{"ista":"Salvador CEM, Pieber B, Neu PM, Torvisco A, Kleber Z. Andrade C, Kappe CO. 2015. A sequential Ugi multicomponent/Cu-catalyzed azide–alkyne cycloaddition approach for the continuous flow generation of cyclic peptoids. The Journal of Organic Chemistry. 80(9), 4590–4602.","ama":"Salvador CEM, Pieber B, Neu PM, Torvisco A, Kleber Z. Andrade C, Kappe CO. A sequential Ugi multicomponent/Cu-catalyzed azide–alkyne cycloaddition approach for the continuous flow generation of cyclic peptoids. <i>The Journal of Organic Chemistry</i>. 2015;80(9):4590-4602. doi:<a href=\"https://doi.org/10.1021/acs.joc.5b00445\">10.1021/acs.joc.5b00445</a>","chicago":"Salvador, Carlos Eduardo M., Bartholomäus Pieber, Philipp M. Neu, Ana Torvisco, Carlos Kleber Z. Andrade, and C. Oliver Kappe. “A Sequential Ugi Multicomponent/Cu-Catalyzed Azide–Alkyne Cycloaddition Approach for the Continuous Flow Generation of Cyclic Peptoids.” <i>The Journal of Organic Chemistry</i>. American Chemical Society, 2015. <a href=\"https://doi.org/10.1021/acs.joc.5b00445\">https://doi.org/10.1021/acs.joc.5b00445</a>.","ieee":"C. E. M. Salvador, B. Pieber, P. M. Neu, A. Torvisco, C. Kleber Z. Andrade, and C. O. Kappe, “A sequential Ugi multicomponent/Cu-catalyzed azide–alkyne cycloaddition approach for the continuous flow generation of cyclic peptoids,” <i>The Journal of Organic Chemistry</i>, vol. 80, no. 9. American Chemical Society, pp. 4590–4602, 2015.","short":"C.E.M. Salvador, B. Pieber, P.M. Neu, A. Torvisco, C. Kleber Z. Andrade, C.O. Kappe, The Journal of Organic Chemistry 80 (2015) 4590–4602.","mla":"Salvador, Carlos Eduardo M., et al. “A Sequential Ugi Multicomponent/Cu-Catalyzed Azide–Alkyne Cycloaddition Approach for the Continuous Flow Generation of Cyclic Peptoids.” <i>The Journal of Organic Chemistry</i>, vol. 80, no. 9, American Chemical Society, 2015, pp. 4590–602, doi:<a href=\"https://doi.org/10.1021/acs.joc.5b00445\">10.1021/acs.joc.5b00445</a>.","apa":"Salvador, C. E. M., Pieber, B., Neu, P. M., Torvisco, A., Kleber Z. Andrade, C., &#38; Kappe, C. O. (2015). A sequential Ugi multicomponent/Cu-catalyzed azide–alkyne cycloaddition approach for the continuous flow generation of cyclic peptoids. <i>The Journal of Organic Chemistry</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/acs.joc.5b00445\">https://doi.org/10.1021/acs.joc.5b00445</a>"},"day":"01","quality_controlled":"1","type":"journal_article","external_id":{"pmid":["25842982"]},"abstract":[{"lang":"eng","text":"The development of a continuous flow multistep strategy for the synthesis of linear peptoids and their subsequent macrocyclization via Click chemistry is described. The central transformation of this process is an Ugi four-component reaction generating the peptidomimetic core structure. In order to avoid exposure to the often toxic and malodorous isocyanide building blocks, the continuous approach was telescoped by the dehydration of the corresponding formamide. In a concurrent operation, the highly energetic azide moiety required for the subsequent intramolecular copper-catalyzed azide–alkyne cycloaddition (Click reaction) was installed by nucleophilic substitution from a bromide precursor. All steps yielding to the linear core structures can be conveniently coupled without the need for purification steps resulting in a single process generating the desired peptidomimetics in good to excellent yields within a 25 min reaction time. The following macrocyclization was realized in a coil reactor made of copper without any additional additive. A careful process intensification study demonstrated that this transformation occurs quantitatively within 25 min at 140 °C. Depending on the resulting ring strain, either a dimeric or a monomeric form of the cyclic product was obtained."}],"_id":"11977","language":[{"iso":"eng"}],"date_published":"2015-05-01T00:00:00Z","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","year":"2015","intvolume":"        80","date_updated":"2023-02-21T10:10:04Z","publication":"The Journal of Organic Chemistry","scopus_import":"1","issue":"9","status":"public","page":"4590-4602","publication_status":"published","oa_version":"None","date_created":"2022-08-25T10:52:24Z","title":"A sequential Ugi multicomponent/Cu-catalyzed azide–alkyne cycloaddition approach for the continuous flow generation of cyclic peptoids","publication_identifier":{"eissn":["1520-6904"],"issn":["0022-3263"]},"month":"05","article_type":"original","volume":80,"author":[{"full_name":"Salvador, Carlos Eduardo M.","last_name":"Salvador","first_name":"Carlos Eduardo M."},{"id":"93e5e5b2-0da6-11ed-8a41-af589a024726","first_name":"Bartholomäus","orcid":"0000-0001-8689-388X","last_name":"Pieber","full_name":"Pieber, Bartholomäus"},{"first_name":"Philipp M.","full_name":"Neu, Philipp M.","last_name":"Neu"},{"last_name":"Torvisco","full_name":"Torvisco, Ana","first_name":"Ana"},{"full_name":"Kleber Z. Andrade, Carlos","last_name":"Kleber Z. Andrade","first_name":"Carlos"},{"first_name":"C. Oliver","last_name":"Kappe","full_name":"Kappe, C. Oliver"}],"doi":"10.1021/acs.joc.5b00445","pmid":1,"extern":"1","publisher":"American Chemical Society","article_processing_charge":"No"},{"citation":{"ama":"Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. <i>The Journal of Organic Chemistry</i>. 2014;79(15):7199-7204. doi:<a href=\"https://doi.org/10.1021/jo500773t\">10.1021/jo500773t</a>","ista":"Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. 2014. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. The Journal of Organic Chemistry. 79(15), 7199–7204.","chicago":"Guan, Weiye, Alicia K. Michael, Melissa L. McIntosh, Liza Koren-Selfridge, John P. Scott, and Timothy B. Clark. “Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters.” <i>The Journal of Organic Chemistry</i>. American Chemical Society, 2014. <a href=\"https://doi.org/10.1021/jo500773t\">https://doi.org/10.1021/jo500773t</a>.","mla":"Guan, Weiye, et al. “Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters.” <i>The Journal of Organic Chemistry</i>, vol. 79, no. 15, American Chemical Society, 2014, pp. 7199–204, doi:<a href=\"https://doi.org/10.1021/jo500773t\">10.1021/jo500773t</a>.","ieee":"W. Guan, A. K. Michael, M. L. McIntosh, L. Koren-Selfridge, J. P. Scott, and T. B. Clark, “Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters,” <i>The Journal of Organic Chemistry</i>, vol. 79, no. 15. American Chemical Society, pp. 7199–7204, 2014.","short":"W. Guan, A.K. Michael, M.L. McIntosh, L. Koren-Selfridge, J.P. Scott, T.B. Clark, The Journal of Organic Chemistry 79 (2014) 7199–7204.","apa":"Guan, W., Michael, A. K., McIntosh, M. L., Koren-Selfridge, L., Scott, J. P., &#38; Clark, T. B. (2014). Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. <i>The Journal of Organic Chemistry</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/jo500773t\">https://doi.org/10.1021/jo500773t</a>"},"day":"10","type":"journal_article","quality_controlled":"1","abstract":[{"text":"The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki–Miyaura coupling reaction to obtain alkenes of known geometry.","lang":"eng"}],"_id":"15161","language":[{"iso":"eng"}],"main_file_link":[{"open_access":"1","url":"https://doi.org/10.1021/jo500773t"}],"date_published":"2014-06-10T00:00:00Z","year":"2014","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","intvolume":"        79","date_updated":"2024-03-25T11:50:01Z","publication":"The Journal of Organic Chemistry","scopus_import":"1","issue":"15","page":"7199-7204","status":"public","publication_status":"published","oa_version":"Published Version","title":"Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters","date_created":"2024-03-21T07:58:31Z","publication_identifier":{"eissn":["1520-6904"],"issn":["0022-3263"]},"keyword":["Organic Chemistry"],"article_type":"letter_note","month":"06","author":[{"first_name":"Weiye","last_name":"Guan","full_name":"Guan, Weiye"},{"last_name":"Michael","full_name":"Michael, Alicia Kathleen","first_name":"Alicia Kathleen","id":"6437c950-2a03-11ee-914d-d6476dd7b75c"},{"first_name":"Melissa L.","full_name":"McIntosh, Melissa L.","last_name":"McIntosh"},{"first_name":"Liza","full_name":"Koren-Selfridge, Liza","last_name":"Koren-Selfridge"},{"full_name":"Scott, John P.","last_name":"Scott","first_name":"John P."},{"first_name":"Timothy B.","last_name":"Clark","full_name":"Clark, Timothy B."}],"volume":79,"doi":"10.1021/jo500773t","oa":1,"extern":"1","publisher":"American Chemical Society","article_processing_charge":"No"}]