---
_id: '18209'
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.
article_processing_charge: No
article_type: original
author:
- first_name: Tomer
  full_name: Weiss, Tomer
  last_name: Weiss
- first_name: Alexandra
  full_name: Wahab, Alexandra
  last_name: Wahab
- first_name: Alexander
  full_name: Bronstein, Alexander
  id: 58f3726e-7cba-11ef-ad8b-e6e8cb3904e6
  last_name: Bronstein
  orcid: 0000-0001-9699-8730
- first_name: Renana
  full_name: Gershoni-Poranne, Renana
  last_name: Gershoni-Poranne
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>
  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>
  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>.
  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.
  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.
  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>.
  short: T. Weiss, A. Wahab, A.M. Bronstein, R. Gershoni-Poranne, The Journal of Organic
    Chemistry 88 (2023) 9645–9656.
date_created: 2024-10-08T12:47:17Z
date_published: 2023-01-25T00:00:00Z
date_updated: 2024-10-09T10:49:42Z
day: '25'
doi: 10.1021/acs.joc.2c02381
extern: '1'
external_id:
  pmid:
  - '36696660'
intvolume: '        88'
issue: '14'
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: 10.26434/chemrxiv-2022-krng1
month: '01'
oa: 1
oa_version: Preprint
page: 9645-9656
pmid: 1
publication: The Journal of Organic Chemistry
publication_identifier:
  eissn:
  - 1520-6904
  issn:
  - 0022-3263
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Interpretable deep-learning unveils structure–property relationships in polybenzenoid
  hydrocarbons
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 88
year: '2023'
...
---
_id: '11977'
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.
article_processing_charge: No
article_type: original
author:
- first_name: Carlos Eduardo M.
  full_name: Salvador, Carlos Eduardo M.
  last_name: Salvador
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
- first_name: Philipp M.
  full_name: Neu, Philipp M.
  last_name: Neu
- first_name: Ana
  full_name: Torvisco, Ana
  last_name: Torvisco
- first_name: Carlos
  full_name: Kleber Z. Andrade, Carlos
  last_name: Kleber Z. Andrade
- first_name: C. Oliver
  full_name: Kappe, C. Oliver
  last_name: Kappe
citation:
  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>
  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>
  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.
  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.
  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>.
  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.
date_created: 2022-08-25T10:52:24Z
date_published: 2015-05-01T00:00:00Z
date_updated: 2023-02-21T10:10:04Z
day: '01'
doi: 10.1021/acs.joc.5b00445
extern: '1'
external_id:
  pmid:
  - '25842982'
intvolume: '        80'
issue: '9'
language:
- iso: eng
month: '05'
oa_version: None
page: 4590-4602
pmid: 1
publication: The Journal of Organic Chemistry
publication_identifier:
  eissn:
  - 1520-6904
  issn:
  - 0022-3263
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: A sequential Ugi multicomponent/Cu-catalyzed azide–alkyne cycloaddition approach
  for the continuous flow generation of cyclic peptoids
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 80
year: '2015'
...
---
_id: '15161'
abstract:
- lang: eng
  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.
article_processing_charge: No
article_type: letter_note
author:
- first_name: Weiye
  full_name: Guan, Weiye
  last_name: Guan
- first_name: Alicia Kathleen
  full_name: Michael, Alicia Kathleen
  id: 6437c950-2a03-11ee-914d-d6476dd7b75c
  last_name: Michael
- first_name: Melissa L.
  full_name: McIntosh, Melissa L.
  last_name: McIntosh
- first_name: Liza
  full_name: Koren-Selfridge, Liza
  last_name: Koren-Selfridge
- first_name: John P.
  full_name: Scott, John P.
  last_name: Scott
- first_name: Timothy B.
  full_name: Clark, Timothy B.
  last_name: Clark
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>
  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>
  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>.
  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.
  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.
  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>.
  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.
date_created: 2024-03-21T07:58:31Z
date_published: 2014-06-10T00:00:00Z
date_updated: 2024-03-25T11:50:01Z
day: '10'
doi: 10.1021/jo500773t
extern: '1'
intvolume: '        79'
issue: '15'
keyword:
- Organic Chemistry
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: https://doi.org/10.1021/jo500773t
month: '06'
oa: 1
oa_version: Published Version
page: 7199-7204
publication: The Journal of Organic Chemistry
publication_identifier:
  eissn:
  - 1520-6904
  issn:
  - 0022-3263
publication_status: published
publisher: American Chemical Society
quality_controlled: '1'
scopus_import: '1'
status: public
title: Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated
  elimination of α-hydroxyboronate esters
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 79
year: '2014'
...