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Structural and Reactivity Analyses of Nitrofurantoin–4-dimethylaminopyridine Salt Using Spectroscopic and Density Functional Theory Calculations

1
Department of Physics, University of Lucknow, Lucknow 226 007, India
2
Centre for Pharmaceutical Engineering Science and School of Pharmacy and Medical Sciences, University of Bradford, Bradford BD7 1DP, UK
*
Authors to whom correspondence should be addressed.
Crystals 2019, 9(8), 413; https://doi.org/10.3390/cryst9080413
Received: 4 July 2019 / Revised: 6 August 2019 / Accepted: 6 August 2019 / Published: 9 August 2019
(This article belongs to the Special Issue Pharmaceutical Crystals)
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Abstract

Pharmaceutical salt, nitrofurantoin–4-dimethylaminopyridine (NF-DMAP), along with its native components NF and DMAP are scrutinized by FT-IR and FT-Raman spectroscopy along with density functional theory so that an insight into the H-bond patterns in the respective crystalline lattices can be gained. Two different functionals, B3LYP and wB97X-D, have been used to compare the theoretical results. The FT-IR spectra obtained for NF-DMAP and NF clearly validate the presence of C33–H34⋅⋅⋅O4 and N23–H24⋅⋅⋅N9 hydrogen bonds by shifting in the stretching vibration of –NH and –CH group of DMAP+ towards the lower wavenumber side. To explore the significance of hydrogen bonding, quantum theory of atoms in molecules (QTAIM) has been employed, and the findings suggest that the N23–H24⋅⋅⋅N9 bond is a strong intermolecular hydrogen bond. The decrement in the HOMO-LUMO gap, which is calculated from NF → NF-DMAP, reveals that the active pharmaceutical ingredient is chemically less reactive compared to the salt. The electrophilicity index (ω) profiles for NF and DMAP confirms that NF is acting as electron acceptor while DMAP acts as electron donor. The reactive sites of the salt are plotted by molecular electrostatic potential (MEP) surface and calculated using local reactivity descriptors. View Full-Text
Keywords: Nitrofurantoin–4-dimethylaminopyridine (NF-DMAP) salt; DFT study; HOMO-LUMO; reactivity descriptors; hydrogen bonding Nitrofurantoin–4-dimethylaminopyridine (NF-DMAP) salt; DFT study; HOMO-LUMO; reactivity descriptors; hydrogen bonding
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Khan, E.; Shukla, A.; Srivastava, K.; Gangopadhyay, D.; Assi, K.H.; Tandon, P.; Vangala, V.R. Structural and Reactivity Analyses of Nitrofurantoin–4-dimethylaminopyridine Salt Using Spectroscopic and Density Functional Theory Calculations. Crystals 2019, 9, 413.

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