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Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials.

The Journal of organic chemistry

Chen F, Chen Y, Cao H, Xu Q, Yu L.
PMID: 30335381
J Org Chem. 2018 Nov 16;83(22):14158-14164. doi: 10.1021/acs.joc.8b02275. Epub 2018 Oct 24.

Copper-catalyzed coupling of Grignard reagents with pent-1-en-4-yn-3-yl benzoates occurs regioselectively at the terminal alkenyl carbon rather than the alkynyl site, leading to the stereoselective formation of unexpected ( Z) -1,5-disubstituted pent-3-en-1-ynes without generation of the initially expected alkenyl allene...

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Chen F, Chen Y, Cao H, et al. Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials. J Org Chem. 2018;83(22):14158-14164doi: 10.1021/acs.joc.8b02275.
Chen, F., Chen, Y., Cao, H., Xu, Q., & Yu, L. (2018). Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials. The Journal of organic chemistry, 83(22), 14158-14164. https://doi.org/10.1021/acs.joc.8b02275
Chen, Fenglin, et al. "Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials." The Journal of organic chemistry vol. 83,22 (2018): 14158-14164. doi: https://doi.org/10.1021/acs.joc.8b02275
Chen F, Chen Y, Cao H, Xu Q, Yu L. Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials. J Org Chem. 2018 Nov 16;83(22):14158-14164. doi: 10.1021/acs.joc.8b02275. Epub 2018 Oct 24. PMID: 30335381.
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The Impact of Salinity on the Interfacial Structuring of an Aromatic Acid at the Calcite/Brine Interface: An Atomistic View on Low Salinity Effect.

The journal of physical chemistry. B

Koleini MM, Badizad MH, Hartkamp R, Ayatollahi S, Ghazanfari MH.
PMID: 31815468
J Phys Chem B. 2020 Jan 09;124(1):224-233. doi: 10.1021/acs.jpcb.9b06987. Epub 2019 Dec 18.

This study aims to elucidate the impact of salinity on the interactions governing the adsorption of polar aromatic oil compounds onto calcite. To this end, molecular dynamics simulations were employed to assess adsorption of a model polar organic molecule...

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Koleini MM, Badizad MH, Hartkamp R, et al. The Impact of Salinity on the Interfacial Structuring of an Aromatic Acid at the Calcite/Brine Interface: An Atomistic View on Low Salinity Effect. J Phys Chem B. 2019;124(1):224-233doi: 10.1021/acs.jpcb.9b06987.
Koleini, M. M., Badizad, M. H., Hartkamp, R., Ayatollahi, S., & Ghazanfari, M. H. (2020). The Impact of Salinity on the Interfacial Structuring of an Aromatic Acid at the Calcite/Brine Interface: An Atomistic View on Low Salinity Effect. The journal of physical chemistry. B, 124(1), 224-233. https://doi.org/10.1021/acs.jpcb.9b06987
Koleini, Mohammad Mehdi, et al. "The Impact of Salinity on the Interfacial Structuring of an Aromatic Acid at the Calcite/Brine Interface: An Atomistic View on Low Salinity Effect." The journal of physical chemistry. B vol. 124,1 (2020): 224-233. doi: https://doi.org/10.1021/acs.jpcb.9b06987
Koleini MM, Badizad MH, Hartkamp R, Ayatollahi S, Ghazanfari MH. The Impact of Salinity on the Interfacial Structuring of an Aromatic Acid at the Calcite/Brine Interface: An Atomistic View on Low Salinity Effect. J Phys Chem B. 2020 Jan 09;124(1):224-233. doi: 10.1021/acs.jpcb.9b06987. Epub 2019 Dec 18. PMID: 31815468.
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Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates.

Acta crystallographica. Section C, Structural chemistry

Tamboli MI, Krishanaswamy S, Gonnade RG, Shashidhar MS.
PMID: 27811429
Acta Crystallogr C Struct Chem. 2016 Nov 01;72:875-881. doi: 10.1107/S205322961601603X. Epub 2016 Oct 24.

Minor variations in the molecular structure of constituent molecules of reactive crystals often yield crystals with significantly different properties due to altered modes of molecular association in the solid state. Hence, these studies could provide a better understanding of...

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Tamboli MI, Krishanaswamy S, Gonnade RG, et al. Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates. Acta Crystallogr C Struct Chem. 2016;72:875-881doi: 10.1107/S205322961601603X.
Tamboli, M. I., Krishanaswamy, S., Gonnade, R. G., & Shashidhar, M. S. (2016). Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates. Acta crystallographica. Section C, Structural chemistry, 72875-881. https://doi.org/10.1107/S205322961601603X
Tamboli, Majid I, et al. "Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates." Acta crystallographica. Section C, Structural chemistry vol. 72 (2016): 875-881. doi: https://doi.org/10.1107/S205322961601603X
Tamboli MI, Krishanaswamy S, Gonnade RG, Shashidhar MS. Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates. Acta Crystallogr C Struct Chem. 2016 Nov 01;72:875-881. doi: 10.1107/S205322961601603X. Epub 2016 Oct 24. PMID: 27811429.
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Layered hydroxide nickel benzoates: hydrothermal synthesis, structure characterization, and exfoliation reaction.

Journal of colloid and interface science

Xu Y, Kominami K, Ishikawa Y, Feng Q.
PMID: 22897953
J Colloid Interface Sci. 2012 Nov 15;386(1):107-13. doi: 10.1016/j.jcis.2012.07.046. Epub 2012 Jul 24.

This paper introduces two hydrothermally synthesized layered hydroxide nickel benzoates with the layered basic metal salt structures of basal spacings of 1.71 and 1.48 nm and their exfoliation reactions. These inorganic-organic hybrid layered compounds were characterized with XRD, FTIR,...

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Xu Y, Kominami K, Ishikawa Y, et al. Layered hydroxide nickel benzoates: hydrothermal synthesis, structure characterization, and exfoliation reaction. J Colloid Interface Sci. 2012;386(1):107-13doi: 10.1016/j.jcis.2012.07.046.
Xu, Y., Kominami, K., Ishikawa, Y., & Feng, Q. (2012). Layered hydroxide nickel benzoates: hydrothermal synthesis, structure characterization, and exfoliation reaction. Journal of colloid and interface science, 386(1), 107-13. https://doi.org/10.1016/j.jcis.2012.07.046
Xu, Yaohua, et al. "Layered hydroxide nickel benzoates: hydrothermal synthesis, structure characterization, and exfoliation reaction." Journal of colloid and interface science vol. 386,1 (2012): 107-13. doi: https://doi.org/10.1016/j.jcis.2012.07.046
Xu Y, Kominami K, Ishikawa Y, Feng Q. Layered hydroxide nickel benzoates: hydrothermal synthesis, structure characterization, and exfoliation reaction. J Colloid Interface Sci. 2012 Nov 15;386(1):107-13. doi: 10.1016/j.jcis.2012.07.046. Epub 2012 Jul 24. PMID: 22897953.
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Protective effect of blackthorn fruits (.

BMC chemistry

Balta I, Sevastre B, Mireşan V, Taulescu M, Raducu C, Longodor AL, Marchiş Z, Mariş CS, Coroian A.
PMID: 31417987
BMC Chem. 2019 Aug 09;13(1):104. doi: 10.1186/s13065-019-0610-y. eCollection 2019 Dec.

BACKGROUND: Tartrazine (Yellow 5 or E102) is a synthetic food dye able to modify perception and behavior, causing agitation, confusion, rhinitis and can produce hyperactivity syndrome in children when is combined with benzoates. Additionally, it can trigger oxidative stress...

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Balta I, Sevastre B, Mireşan V, et al. Protective effect of blackthorn fruits (. BMC Chem. 2019;13(1):104doi: 10.1186/s13065-019-0610-y.
Balta, I., Sevastre, B., Mireşan, V., Taulescu, M., Raducu, C., Longodor, A. L., Marchiş, Z., Mariş, C. S., & Coroian, A. (2019). Protective effect of blackthorn fruits (. BMC chemistry, 13(1), 104. https://doi.org/10.1186/s13065-019-0610-y
Balta, Igori, et al. "Protective effect of blackthorn fruits (." BMC chemistry vol. 13,1 (2019): 104. doi: https://doi.org/10.1186/s13065-019-0610-y
Balta I, Sevastre B, Mireşan V, Taulescu M, Raducu C, Longodor AL, Marchiş Z, Mariş CS, Coroian A. Protective effect of blackthorn fruits (. BMC Chem. 2019 Aug 09;13(1):104. doi: 10.1186/s13065-019-0610-y. eCollection 2019 Dec. PMID: 31417987; PMCID: PMC6688354.
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α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters.

Journal of the American Chemical Society

Casoni G, Kucukdisli M, Fordham JM, Burns M, Myers EL, Aggarwal VK.
PMID: 28812893
J Am Chem Soc. 2017 Aug 30;139(34):11877-11886. doi: 10.1021/jacs.7b05457. Epub 2017 Aug 16.

The stereoselective reagent-controlled homologation of boronic esters is one of a small number of iteratable synthetic transformations that if automated could form the basis of a veritable molecule-making machine. Recently, α-stannyl triisopropylbenzoates and α-sulfinyl chlorides have emerged as useful...

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Casoni G, Kucukdisli M, Fordham JM, et al. α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters. J Am Chem Soc. 2017;139(34):11877-11886doi: 10.1021/jacs.7b05457.
Casoni, G., Kucukdisli, M., Fordham, J. M., Burns, M., Myers, E. L., & Aggarwal, V. K. (2017). α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters. Journal of the American Chemical Society, 139(34), 11877-11886. https://doi.org/10.1021/jacs.7b05457
Casoni, Giorgia, et al. "α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters." Journal of the American Chemical Society vol. 139,34 (2017): 11877-11886. doi: https://doi.org/10.1021/jacs.7b05457
Casoni G, Kucukdisli M, Fordham JM, Burns M, Myers EL, Aggarwal VK. α-Sulfinyl Benzoates as Precursors to Li and Mg Carbenoids for the Stereoselective Iterative Homologation of Boronic Esters. J Am Chem Soc. 2017 Aug 30;139(34):11877-11886. doi: 10.1021/jacs.7b05457. Epub 2017 Aug 16. PMID: 28812893.
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Tipping the Balance between Concerted versus Sequential Proton-Coupled Electron Transfer.

Inorganic chemistry

Kretchmer JS, Miller TF.
PMID: 26440812
Inorg Chem. 2016 Feb 01;55(3):1022-31. doi: 10.1021/acs.inorgchem.5b01821. Epub 2015 Oct 06.

We use quantized molecular dynamics simulations to investigate the competition between concerted and sequential proton-coupled electron-transfer (PCET) reaction mechanisms in inorganic catalysts. By analyzing reactive nonadiabatic PCET trajectories and computing both concerted and sequential rate constants, we characterize various...

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Kretchmer JS, Miller TF. Tipping the Balance between Concerted versus Sequential Proton-Coupled Electron Transfer. Inorg Chem. 2015;55(3):1022-31doi: 10.1021/acs.inorgchem.5b01821.
Kretchmer, J. S., & Miller, T. F. (2016). Tipping the Balance between Concerted versus Sequential Proton-Coupled Electron Transfer. Inorganic chemistry, 55(3), 1022-31. https://doi.org/10.1021/acs.inorgchem.5b01821
Kretchmer, Joshua S, and Miller, Thomas F. "Tipping the Balance between Concerted versus Sequential Proton-Coupled Electron Transfer." Inorganic chemistry vol. 55,3 (2016): 1022-31. doi: https://doi.org/10.1021/acs.inorgchem.5b01821
Kretchmer JS, Miller TF. Tipping the Balance between Concerted versus Sequential Proton-Coupled Electron Transfer. Inorg Chem. 2016 Feb 01;55(3):1022-31. doi: 10.1021/acs.inorgchem.5b01821. Epub 2015 Oct 06. PMID: 26440812.
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[Rapid analysis of the specific migration of seven terephthalates and benzoates from plastic food contact material and products by high performance liquid chromatography-ultraviolet detection].

Se pu = Chinese journal of chromatography

Xiao X, Wang J, Liu T, He J, Chen T, Wang J.
PMID: 34213143
Se Pu. 2019 Dec 08;37(12):1383-1391. doi: 10.3724/SP.J.1123.2019.06021.

A method based on high-performance liquid chromatography-ultraviolet (HPLC-UV) detection was developed for the rapid analysis of the specific migration of seven terephthalates and benzoates (TPBAs) in seven food simulants (10% (v/v) ethanol, 3% (m/v, i. e. 3 g/100 mL)...

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Xiao X, Wang J, Liu T, et al. [Rapid analysis of the specific migration of seven terephthalates and benzoates from plastic food contact material and products by high performance liquid chromatography-ultraviolet detection]. Se Pu. 2019;37(12):1383-1391doi: 10.3724/SP.J.1123.2019.06021.
Xiao, X., Wang, J., Liu, T., He, J., Chen, T., & Wang, J. (2019). [Rapid analysis of the specific migration of seven terephthalates and benzoates from plastic food contact material and products by high performance liquid chromatography-ultraviolet detection]. Se pu = Chinese journal of chromatography, 37(12), 1383-1391. https://doi.org/10.3724/SP.J.1123.2019.06021
Xiao, Xiaofeng, et al. "[Rapid analysis of the specific migration of seven terephthalates and benzoates from plastic food contact material and products by high performance liquid chromatography-ultraviolet detection]." Se pu = Chinese journal of chromatography vol. 37,12 (2019): 1383-1391. doi: https://doi.org/10.3724/SP.J.1123.2019.06021
Xiao X, Wang J, Liu T, He J, Chen T, Wang J. [Rapid analysis of the specific migration of seven terephthalates and benzoates from plastic food contact material and products by high performance liquid chromatography-ultraviolet detection]. Se Pu. 2019 Dec 08;37(12):1383-1391. doi: 10.3724/SP.J.1123.2019.06021. Chinese. PMID: 34213143.
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"Meta elimination," a diagnostic fragmentation in mass spectrometry.

Journal of the American Society for Mass Spectrometry

Attygalle AB, Nishshanka U, Weisbecker CS.
PMID: 21953255
J Am Soc Mass Spectrom. 2011 Sep;22(9):1515-25. doi: 10.1007/s13361-011-0164-2. Epub 2011 Jun 03.

The diagnostic value of the "ortho effect" for unknown identification by mass spectrometry is well known. Here, we report the existence of a novel "meta effect," which adds to the repertoire of useful mass spectrometric fragmentation mechanisms. For example,...

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Attygalle AB, Nishshanka U, Weisbecker CS. "Meta elimination," a diagnostic fragmentation in mass spectrometry. J Am Soc Mass Spectrom. 2011;22(9):1515-25doi: 10.1007/s13361-011-0164-2.
Attygalle, A. B., Nishshanka, U., & Weisbecker, C. S. (2011). "Meta elimination," a diagnostic fragmentation in mass spectrometry. Journal of the American Society for Mass Spectrometry, 22(9), 1515-25. https://doi.org/10.1007/s13361-011-0164-2
Attygalle, Athula B, et al. ""Meta elimination," a diagnostic fragmentation in mass spectrometry." Journal of the American Society for Mass Spectrometry vol. 22,9 (2011): 1515-25. doi: https://doi.org/10.1007/s13361-011-0164-2
Attygalle AB, Nishshanka U, Weisbecker CS. "Meta elimination," a diagnostic fragmentation in mass spectrometry. J Am Soc Mass Spectrom. 2011 Sep;22(9):1515-25. doi: 10.1007/s13361-011-0164-2. Epub 2011 Jun 03. PMID: 21953255.
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Solid-state 17O NMR study of benzoic acid adsorption on metal oxide surfaces.

Solid state nuclear magnetic resonance

Hagaman EW, Chen B, Jiao J, Parsons W.
PMID: 22245610
Solid State Nucl Magn Reson. 2012 Feb;41:60-7. doi: 10.1016/j.ssnmr.2011.12.001. Epub 2011 Dec 21.

Solid-state (17)O NMR spectra of (17)O-labeled benzoic and anisic acids are reported and benzoic acid is used to probe the surface of metal oxides. Complexes formed when benzoic acid is dry mixed with mesoporous silica, and nonporous titania and...

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Hagaman EW, Chen B, Jiao J, et al. Solid-state 17O NMR study of benzoic acid adsorption on metal oxide surfaces. Solid State Nucl Magn Reson. 2011;41:60-7doi: 10.1016/j.ssnmr.2011.12.001.
Hagaman, E. W., Chen, B., Jiao, J., & Parsons, W. (2012). Solid-state 17O NMR study of benzoic acid adsorption on metal oxide surfaces. Solid state nuclear magnetic resonance, 4160-7. https://doi.org/10.1016/j.ssnmr.2011.12.001
Hagaman, Edward W, et al. "Solid-state 17O NMR study of benzoic acid adsorption on metal oxide surfaces." Solid state nuclear magnetic resonance vol. 41 (2012): 60-7. doi: https://doi.org/10.1016/j.ssnmr.2011.12.001
Hagaman EW, Chen B, Jiao J, Parsons W. Solid-state 17O NMR study of benzoic acid adsorption on metal oxide surfaces. Solid State Nucl Magn Reson. 2012 Feb;41:60-7. doi: 10.1016/j.ssnmr.2011.12.001. Epub 2011 Dec 21. PMID: 22245610.
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A dedicated flavin-dependent monooxygenase catalyzes the hydroxylation of demethoxyubiquinone into ubiquinone (coenzyme Q) in Arabidopsis.

The Journal of biological chemistry

Latimer S, Keene SA, Stutts LR, Berger A, Bernert AC, Soubeyrand E, Wright J, Clarke CF, Block AK, Colquhoun TA, Elowsky C, Christensen A, Wilson MA, Basset GJ.
PMID: 34626646
J Biol Chem. 2021 Nov;297(5):101283. doi: 10.1016/j.jbc.2021.101283. Epub 2021 Oct 06.

Ubiquinone (Coenzyme Q) is a vital respiratory cofactor and liposoluble antioxidant. In plants, it is not known how the C-6 hydroxylation of demethoxyubiquinone, the penultimate step in ubiquinone biosynthesis, is catalyzed. The combination of cross-species gene network modeling along...

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Latimer S, Keene SA, Stutts LR, et al. A dedicated flavin-dependent monooxygenase catalyzes the hydroxylation of demethoxyubiquinone into ubiquinone (coenzyme Q) in Arabidopsis. J Biol Chem. 2021;297(5):101283doi: 10.1016/j.jbc.2021.101283.
Latimer, S., Keene, S. A., Stutts, L. R., Berger, A., Bernert, A. C., Soubeyrand, E., Wright, J., Clarke, C. F., Block, A. K., Colquhoun, T. A., Elowsky, C., Christensen, A., Wilson, M. A., & Basset, G. J. (2021). A dedicated flavin-dependent monooxygenase catalyzes the hydroxylation of demethoxyubiquinone into ubiquinone (coenzyme Q) in Arabidopsis. The Journal of biological chemistry, 297(5), 101283. https://doi.org/10.1016/j.jbc.2021.101283
Latimer, Scott, et al. "A dedicated flavin-dependent monooxygenase catalyzes the hydroxylation of demethoxyubiquinone into ubiquinone (coenzyme Q) in Arabidopsis." The Journal of biological chemistry vol. 297,5 (2021): 101283. doi: https://doi.org/10.1016/j.jbc.2021.101283
Latimer S, Keene SA, Stutts LR, Berger A, Bernert AC, Soubeyrand E, Wright J, Clarke CF, Block AK, Colquhoun TA, Elowsky C, Christensen A, Wilson MA, Basset GJ. A dedicated flavin-dependent monooxygenase catalyzes the hydroxylation of demethoxyubiquinone into ubiquinone (coenzyme Q) in Arabidopsis. J Biol Chem. 2021 Nov;297(5):101283. doi: 10.1016/j.jbc.2021.101283. Epub 2021 Oct 06. PMID: 34626646; PMCID: PMC8559556.
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