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Context <p>A 1:1 supramolecular cocrystal of febuxostat (FXT) and urea was investigated to elucidate its structural, electronic, thermodynamic, and non-linear optical (NLO) characteristics. Ground-state geometry optimization (−2029.1013 a.u.) of an extended FXT+3urea model revealed a highly stable hydrogen-bonded architecture, driven by complementary electrostatic extremes identified via MESP mapping. QTAIM analysis confirmed that the primary intermolecular hydrogen bonds possess partial covalent character with a maximum stabilization energy of −17.14&#xa0;kcal/mol. This stability is governed by massive donor-acceptor interactions, notably an NBO lone pair to antibonding transition (n(O39) → σ*(C14–H15)). Frontier molecular orbital analysis indicated a narrowed HOMO-LUMO gap (4.09&#xa0;eV) upon cocrystallization, demonstrating enhanced chemical reactivity. Furthermore, the cocrystal exhibited theoretically validated thermodynamic stability (C<sup>0</sup><sub>p,m</sub>, S<sup>0</sup><sub>m</sub>, H<sup>0</sup><sub>m</sub>) and elevated molar refractivity (67.956 e.s.u., 50.925 e.s.u. for isolated FXT). Macroscopic charge redistribution also resulted in an 11-fold increase in the first hyperpolarizability (9.135 × 10⁻<sup>30</sup> e.s.u), highlighting exceptional NLO performance.</p> Methods <p>Pure FXT was isolated from commercial tablets and verified via UV-visible spectroscopy. Cocrystals were synthesized via solvent evaporation. Quantum chemical computations were performed using DFT at the B3LYP/6-311++G(d,p) level. Calculated vibrational spectra exhibited strong agreement with experimental FT-IR results. Intermolecular interactions and electronic properties were quantitatively assessed using QTAIM, NBO, and MESP analyses.</p>

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Experimental and theoretical insights into the hydrogen bonding and electronic structure of febuxostat–urea cocrystal: a combined FT-IR and DFT study

  • 期刊论文

  • 发表日期：

    2026年5月12日

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  • Sarita Yadav,
  • Anuradha Shukla,
  • Shamoon Ahmad Siddiqui,
  • Priya Verma,
  • Tahira Khatoon

摘要

Context

A 1:1 supramolecular cocrystal of febuxostat (FXT) and urea was investigated to elucidate its structural, electronic, thermodynamic, and non-linear optical (NLO) characteristics. Ground-state geometry optimization (−2029.1013 a.u.) of an extended FXT+3urea model revealed a highly stable hydrogen-bonded architecture, driven by complementary electrostatic extremes identified via MESP mapping. QTAIM analysis confirmed that the primary intermolecular hydrogen bonds possess partial covalent character with a maximum stabilization energy of −17.14 kcal/mol. This stability is governed by massive donor-acceptor interactions, notably an NBO lone pair to antibonding transition (n(O39) → σ*(C14–H15)). Frontier molecular orbital analysis indicated a narrowed HOMO-LUMO gap (4.09 eV) upon cocrystallization, demonstrating enhanced chemical reactivity. Furthermore, the cocrystal exhibited theoretically validated thermodynamic stability (C0p,m, S0m, H0m) and elevated molar refractivity (67.956 e.s.u., 50.925 e.s.u. for isolated FXT). Macroscopic charge redistribution also resulted in an 11-fold increase in the first hyperpolarizability (9.135 × 10⁻30 e.s.u), highlighting exceptional NLO performance.

Methods

Pure FXT was isolated from commercial tablets and verified via UV-visible spectroscopy. Cocrystals were synthesized via solvent evaporation. Quantum chemical computations were performed using DFT at the B3LYP/6-311++G(d,p) level. Calculated vibrational spectra exhibited strong agreement with experimental FT-IR results. Intermolecular interactions and electronic properties were quantitatively assessed using QTAIM, NBO, and MESP analyses.