European Journal of Chemistry

Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline

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Published: Dec 31, 2021
DOI: https://doi.org/10.5155/eurjchem.12.4.419-431.2177
Keywords:
Sulfonamide drugs, Electronic spectrum, Density function theory, Computational chemistry, Hirshfeld surface analysis, Single crystal X-ray diffraction
Section
Research Article
Issue
Vol. 12 No. 4 (2021): December 2021
Dates
Received 2021-08-13
Accepted 2021-10-16
Published 2021-12-31
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Soundararajan Krishnan
Department of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam - 613 403, Thanjavur, Tamil Nadu, India
https://orcid.org/0000-0003-4167-6931
Thanigaimani Kaliyaperumal
Department of Chemistry, Government Arts College, Tiruchirappalli - 620 022, Tamil Nadu, India
https://orcid.org/0000-0002-4384-7848
Ramalingam Marimuthu
Department of Chemistry, Bon Secours College for Women, Thanjavur - 613 006, Tamil Nadu, India
https://orcid.org/0000-0002-0551-5164
Sethuraman Velusamy
Department of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam - 613 403, Thanjavur, Tamil Nadu, India
https://orcid.org/0000-0003-4449-3858

Abstract

The crystal structure investigation of the title compound 4-((pyrrolidin-1-ylsulfonyl) methyl)aniline (PSMA) C11H16N2O2S shows that the molecule is essentially coplanar with a dihedral angle of 26.70(14)°between the pyrrolidine and the benzene rings. A pair of strong N-H···O hydrogen bonds produces continuous two-dimensional sheets with R22(18) ring motifs. The crystal structure also features a weak C-H···π interaction resulting in a three-dimensional network. Density functional theory (DFT) calculations reveal that the experimental and calculated geometric parameters of the molecule are nearly the same. Hirshfeld surface analysis has been carried out to study the various intermolecular interactions responsible for the crystal packing. Theoretical calculations indicate an excellent correlation between the experimental and the simulated UV spectra.


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Krishnan, S.; Kaliyaperumal, T.; Marimuthu, R.; Velusamy, S. Crystal Structure, Hirshfeld Surface, and DFT Studies of 4-(pyrrolidin-1-ylsulfonyl)methyl)aniline. Eur. J. Chem. 2021, 12, 419-431.

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Periyar Maniammai Institute of Science and Technology, Vallam, Thanjavur-613403, Tamilnadu, India.
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