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<p>Sulfonamide derivatives are structurally versatile compounds with relevance to molecular electronics, spectroscopy, and medicinal chemistry. In this study, a cheminformatics-guided physicochemical assessment of 3-bromo-<i>N</i>-tert-butylbenzene-1-sulfonamide (BTBS) was performed by integrating density functional theory, electronic-structure analysis, nonlinear optical descriptors, and preliminary in silico bioactivity assessment. Geometry optimization revealed a rigid sulfonyl framework with a planar aromatic core, while the tert-butyl substituent imposed a non-coplanar sulfonamide orientation that modulates conjugation and charge distribution. Infrared and Raman vibrational assignments reproduced characteristic sulfonamide modes, supporting the proposed bonding framework. The large frontier-orbital energy gap is consistent with high kinetic stability and low intrinsic reactivity, with solvent-dependent stabilization described more effectively by conductor-like continuum models. Electronic-structure and density-of-states analyses revealed functional separation between the aromatic backbone, the electron-withdrawing sulfonamide–bromine unit, and the weakly donating tert-butyl group, indicating intramolecular charge transfer without a classical push–pull architecture. Time-dependent calculations predicted dominant <InlineEquation ID="IEq1"> <EquationSource Format="TEX">\(\pi \)</EquationSource> </InlineEquation>–<InlineEquation ID="IEq2"> <EquationSource Format="TEX">\(\pi ^*\)</EquationSource> </InlineEquation> transitions with solvent-induced red shifts and enhanced oscillator strengths. The calculated first-order hyperpolarizability was higher than the urea reference value, suggesting a molecular-level second-order nonlinear optical response driven by electronic asymmetry. Local reactivity descriptors identified the sulfonamide heteroatoms and brominated ring as the principal reactive regions. Similarity-based read-across and molecular docking provided preliminary computational evidence for possible biological interactions. Overall, BTBS is proposed as a candidate scaffold for follow-up experimental validation at the interface of electronic-material chemistry and medicinal chemoinformatics.</p>

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A cheminformatics and DFT exploration of a brominated sulfonamide with nonlinear optical response and preliminary in silico bioactivity assessment

  • 期刊论文

  • 发表日期：

    2026年7月4日

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  • Bhijan Neupane,
  • Khakendra Basnet,
  • Jeevan Ghimire,
  • Suresh Kumar Dhungel

摘要

Sulfonamide derivatives are structurally versatile compounds with relevance to molecular electronics, spectroscopy, and medicinal chemistry. In this study, a cheminformatics-guided physicochemical assessment of 3-bromo-N-tert-butylbenzene-1-sulfonamide (BTBS) was performed by integrating density functional theory, electronic-structure analysis, nonlinear optical descriptors, and preliminary in silico bioactivity assessment. Geometry optimization revealed a rigid sulfonyl framework with a planar aromatic core, while the tert-butyl substituent imposed a non-coplanar sulfonamide orientation that modulates conjugation and charge distribution. Infrared and Raman vibrational assignments reproduced characteristic sulfonamide modes, supporting the proposed bonding framework. The large frontier-orbital energy gap is consistent with high kinetic stability and low intrinsic reactivity, with solvent-dependent stabilization described more effectively by conductor-like continuum models. Electronic-structure and density-of-states analyses revealed functional separation between the aromatic backbone, the electron-withdrawing sulfonamide–bromine unit, and the weakly donating tert-butyl group, indicating intramolecular charge transfer without a classical push–pull architecture. Time-dependent calculations predicted dominant \(\pi \) – \(\pi ^*\) transitions with solvent-induced red shifts and enhanced oscillator strengths. The calculated first-order hyperpolarizability was higher than the urea reference value, suggesting a molecular-level second-order nonlinear optical response driven by electronic asymmetry. Local reactivity descriptors identified the sulfonamide heteroatoms and brominated ring as the principal reactive regions. Similarity-based read-across and molecular docking provided preliminary computational evidence for possible biological interactions. Overall, BTBS is proposed as a candidate scaffold for follow-up experimental validation at the interface of electronic-material chemistry and medicinal chemoinformatics.