European Journal of Chemistry 2021, 12(2), 109-116 | doi: https://doi.org/10.5155/eurjchem.12.2.109-116.2064 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives


Brock Anton Stenfors (1) orcid , Felix Nyuangem Ngassa (2,*) orcid

(1) Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA
(2) Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401, USA
(*) Corresponding Author

Received: 09 Jan 2021 | Revised: 16 Mar 2021 | Accepted: 28 Mar 2021 | Published: 30 Jun 2021 | Issue Date: June 2021

Abstract


The sulfonamide moiety is present among a variety of biologically significant compounds. A facile synthesis is necessary to produce a variety of sulfonamides with the potential to improve human health. Herein, we report a facile methodology for the synthesis of 4-methylbenzenesulfonamides, amenable to a broad range of nitrogen nucleophiles. Implementing a semi-miscible biphasic solvent system resulted in higher yields, decreased reaction times, and a simplified workup over preliminary methods. Additionally, the crystal structures of five novel sulfonamide compounds and two polymorphs, have been determined by X-ray diffraction. Results obtained through spectroscopic characterization support the successful formation of the desired 4-methylbenzenesulfonamides.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Tosylation; Sulfa drugs; Methodology; Sulfonamides; Crystal structures; Packing polymorph

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.12.2.109-116.2064

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1004 times | icon graph PDF Article downloaded 440 times

Funding information


National Science Foundation (Grant No. MRI CHE-1725699); Grand Valley State University Chemistry Department’s Weldon Fund.

Citations

/


[1]. Fatemeh Rezazadeh-Jabalbarezi, Reza Ranjbar-Karimi, Fariborz Atabaki, Kazem Mohammadiannejad
Site-selective nucleophilic substitution reactions of 2,4,5,6-tetrachloropyrimidine with sulfonamides: Synthesis of novel trichloropyrimidine-arylsulfonamide hybrid derivatives
Journal of Molecular Structure  1271, 133909, 2023
DOI: 10.1016/j.molstruc.2022.133909
/

[2]. Jules Brom, Antoine Maruani, Laurent Micouin, Erica Benedetti
Light-Driven Reductive Cleavage of Sulfonamides Promoted by Thiourea Organophotosensitizers
The Journal of Organic Chemistry  88(9), 5923, 2023
DOI: 10.1021/acs.joc.3c00296
/

References


[1]. Gelmo, P. J. Prakt. Chem. 1908, 77, 369-382.
https://doi.org/10.1002/prac.19080770129

[2]. Domagk, G. Dtsch. Med. Wochenschr. 1935, 61, 250-253.
https://doi.org/10.1055/s-0028-1129486

[3]. Whitby, L. H. Lancet 1938, 231, 1210-1212.
https://doi.org/10.1016/S0140-6736(00)89787-1

[4]. Evans, G. M.; Gaisford, W. Lancet 1938, 232, 14-19.
https://doi.org/10.1016/S0140-6736(00)87996-9

[5]. Apaydın, S.; Török, M. Bioorg. Med. Chem. Lett. 2019, 29, 2042-2050.
https://doi.org/10.1016/j.bmcl.2019.06.041

[6]. Gul, H. I.; Yamali, C.; Sakagami, H.; Angeli, A.; Leitans, J.; Kazaks, A.; Tars, K.; Ozgun, D. O.; Supuran, C. T. Bioorg. Chem. 2018, 77, 411-419.
https://doi.org/10.1016/j.bioorg.2018.01.021

[7]. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. Curr. Med. Chem. 2003, 10, 925-953.
https://doi.org/10.2174/0929867033457647

[8]. Vedovato, V.; Talbot, E. P. A.; Willis, M. C. Org. Lett. 2018, 20, 5493-5496.
https://doi.org/10.1021/acs.orglett.8b02445

[9]. Zhao, Y.; Shadrick, W. R.; Wallace, M. J.; Wu, Y.; Griffith, E. C.; Qi, J.; Yun, M.-K.; White, S. W.; Lee, R. E. Bioorg. Med. Chem. Lett. 2016, 26, 3950-3954.
https://doi.org/10.1016/j.bmcl.2016.07.006

[10]. De Luca, L.; Giacomelli, G. J. Org. Chem. 2008, 73, 3967-3969.
https://doi.org/10.1021/jo800424g

[11]. Mukherjee, P.; Woroch, C. P.; Cleary, L.; Rusznak, M.; Franzese, R. W.; Reese, M. R.; Tucker, J. W.; Humphrey, J. M.; Etuk, S. M.; Kwan, S. C.; am Ende, C. W.; Ball, N. D. Org. Lett. 2018, 20, 3943-3947.
https://doi.org/10.1021/acs.orglett.8b01520

[12]. Patel, Z. S.; Stevens, A. C.; Bookout, E. C.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2018, 74, 1126-1129.
https://doi.org/10.1107/S2056989018010290

[13]. Senger, S.; Chan, C.; Convery, M. A.; Hubbard, J. A.; Shah, G. P.; Watson, N. S.; Young, R. J. Bioorg. Med. Chem. Lett. 2007, 17, 2931-2934.
https://doi.org/10.1016/j.bmcl.2007.02.034

[14]. Schwertz, G.; Frei, M. S.; Witschel, M. C.; Rottmann, M.; Leartsakulpanich, U.; Chitnumsub, P.; Jaruwat, A.; Ittarat, W.; Schäfer, A.; Aponte, R. A.; Trapp, N.; Mark, K.; Chaiyen, P.; Diederich, F. Chemistry 2017, 23, 14345-14357.
https://doi.org/10.1002/chem.201703244

[15]. Willcott, M. R. MestRe Nova MestRe Nova. Mestrelab Research S.L. Feliciano Barrera 9B, Bajo, 15706 Santiago de Compostela, Spain. http://www.mestrelab.com. J. Am. Chem. Soc. 2009, 131, 13180-13180.
https://doi.org/10.1021/ja906709t

[16]. APEX2, Bruker AXS Inc. Madison, Wisconsin, USA, 2013.

[17]. SAINT, Bruker AXS Inc. Madison, Wisconsin, USA, 2013.

[18]. Sheldrick, G. M. Acta Crystallogr. C Struct. Chem. 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[19]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[20]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

[21]. Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Acta Crystallogr. A Found. Adv. 2015, 71, 59-75.
https://doi.org/10.1107/S2053273314022207

[22]. Macrae, C. F.; Sovago, I.; Cottrell, S. J.; Galek, P. T. A.; McCabe, P.; Pidcock, E.; Platings, M.; Shields, G. P.; Stevens, J. S.; Towler, M.; Wood, P. A. J. Appl. Crystallogr. 2020, 53, 226-235.
https://doi.org/10.1107/S1600576719014092

[23]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41, 466-470.
https://doi.org/10.1107/S0021889807067908

[24]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457.
https://doi.org/10.1107/S002188980600731X

[25]. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. B 2002, 58, 389-397.
https://doi.org/10.1107/S0108768102003324

[26]. Taylor, R.; Macrae, C. F. Acta Crystallogr. B 2001, 57, 815-827.
https://doi.org/10.1107/S010876810101360X

[27]. Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2015, 48, 3-10.
https://doi.org/10.1107/S1600576714022985

[28]. Stenfors, B. A.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Chemistry 2020, 2, 591-599.
https://doi.org/10.3390/chemistry2020036

[29]. Stenfors, B. A.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 452-455.
https://doi.org/10.1107/S205698902000208X

[30]. Stenfors, B. A.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 235-238.
https://doi.org/10.1107/S2056989020000535

[31]. Stenfors, B. A.; Collins, R. C.; Duran, J. R. J.; Staples, R. J.; Biros, S. M.; Ngassa, F. N. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 1070-1074.
https://doi.org/10.1107/S2056989020007756

[32]. Yang, L.; Powell, D. R.; Houser, R. P. Dalton Trans. 2007, 955-964.
https://doi.org/10.1039/B617136B

[33]. Gowda, B. T.; Foro, S.; Nirmala, P. G.; Terao, H.; Fuess, H. Acta Crystallogr. Sect. E Struct. Rep. Online 2009, 65, o1219.
https://doi.org/10.1107/S1600536809016377

[34]. Modarresi-Alam, A. R.; Amirazizi, H. A.; Bagheri, H.; Bijanzadeh, H.-R.; Kleinpeter, E. J. Org. Chem. 2009, 74, 4740-4746.
https://doi.org/10.1021/jo900454a


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Stenfors, B.; Ngassa, F. Eur. J. Chem. 2021, 12(2), 109-116. doi:10.5155/eurjchem.12.2.109-116.2064
Stenfors, B.; Ngassa, F. The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives. Eur. J. Chem. 2021, 12(2), 109-116. doi:10.5155/eurjchem.12.2.109-116.2064
Stenfors, B., & Ngassa, F. (2021). The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives. European Journal of Chemistry, 12(2), 109-116. doi:10.5155/eurjchem.12.2.109-116.2064
Stenfors, Brock, & Felix Nyuangem Ngassa. "The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives." European Journal of Chemistry [Online], 12.2 (2021): 109-116. Web. 8 Dec. 2023
Stenfors, Brock, AND Ngassa, Felix. "The synthesis and crystallographic characterization of 4-methylbenzenesulfonamide derivatives" European Journal of Chemistry [Online], Volume 12 Number 2 (30 June 2021)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.12.2.109-116.2064


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2021, 12(2), 109-116 | doi: https://doi.org/10.5155/eurjchem.12.2.109-116.2064 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2021 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.