European Journal of Chemistry 2022, 13(2), 145-150 | doi: https://doi.org/10.5155/eurjchem.13.2.145-150.2279 | Get rights and content

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Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate


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: 06 Apr 2022 | Revised: 12 Apr 2022 | Accepted: 27 Apr 2022 | Published: 30 Jun 2022 | Issue Date: June 2022

Abstract


Arylsulfonates are a useful class of synthetic precursors, affording either their arylamine or arylsulfonamide counterparts upon amination via regioselective C–O/S–O bond cleavage. Herein, the synthesis of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate is described, utilizing our previously developed synthetic methods, and crystallographic characterization. While the mechanism for nucleophilic substitution at the sulfonyl group remains largely unknown, experimental work within our group and in the literature lend credence to a mechanism analogous to its carbonyl counterpart. Characterization of the molecular structure of the title compound, C15H14N2O7S, at 173 K, features a sulfonate group with S=O bond lengths of 1.4198(19) and 1.4183(19) Å and a S–O bond length of 1.6387(18) Å. Viewing down the S–O bond reveals gauche oriented aromatic rings. Crystal data for C15H14N2O7S: Monoclinic, space group P21/c (no. 14), a = 6.8773(10) Å, b = 8.9070(14) Å, c = 25.557(4) Å, β = 93.0630(18)°, V = 1563.3(4) Å3, Z = 4, T = 173.15 K, μ(MoKα) = 0.251 mm-1, Dcalc = 1.557 g/cm3, 12259 reflections measured (3.192° ≤ 2Θ ≤ 50.682°), 2861 unique (Rint = 0.0493, Rsigma = 0.0419) which were used in all calculations. The final R1 was 0.0457 (I > 2σ(I)) and wR2 was 0.1306 (all data).


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Keywords


Crystal; Sulfonate; Sulfonylation; Crystallization; X-ray diffraction; Synthetic methods

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DOI: 10.5155/eurjchem.13.2.145-150.2279

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Funding information


National Science Foundation, Directorate for Mathematical and Physical Sciences (grant No. MRI CHE-1725699; grant No. MRI CHE-1919817); GVSU Chemistry Department’s Weldon Fund.

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

How to cite


Stenfors, B.; Ngassa, F. Eur. J. Chem. 2022, 13(2), 145-150. doi:10.5155/eurjchem.13.2.145-150.2279
Stenfors, B.; Ngassa, F. Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate. Eur. J. Chem. 2022, 13(2), 145-150. doi:10.5155/eurjchem.13.2.145-150.2279
Stenfors, B., & Ngassa, F. (2022). Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate. European Journal of Chemistry, 13(2), 145-150. doi:10.5155/eurjchem.13.2.145-150.2279
Stenfors, Brock, & Felix Nyuangem Ngassa. "Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate." European Journal of Chemistry [Online], 13.2 (2022): 145-150. Web. 30 Nov. 2023
Stenfors, Brock, AND Ngassa, Felix. "Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate" European Journal of Chemistry [Online], Volume 13 Number 2 (30 June 2022)

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