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Molecular Modeling, Spectroscopic Investigations, and Computational Studies of DMSO solvated 7′-amino-1′,3′-dimethyl-2,2′,4′-trioxo-1′,2′,3′,4′,4a′,8a′-tetrahydrospiro[indoline-3,5′-pyrano[2,3-d]pyrimidine]-6′-carbonitrile

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Abstract

A combined experimental and theoretical study is performed on DMSO solvated 7′-amino-1′,3′-dimethyl- 2,2′,4′-trioxo-1′,2′,3′,4′,4a′,8a′-tetrahydrospiro[indoline-3,5′-pyrano[2,3-d]pyrimidine]-6′-carbonitrile. The compound is studied by NMR, IR spectroscopy, and single crystal X-ray analysis. The crystal structure of the molecule is stabilized by intermolecular N–H…N, N–H…O, and C–H…π interactions. In the crystal, the molecules form hydrogen-bonded chains running along the b axis of the unit cell. In the present work, we have applied density functional theory (DFT) to explore the nonlinear properties of the molecule. The harmonic vibrational frequencies are calculated and compared with experimental FT-IR frequencies. The observed and calculated frequencies are found to be in good agreement. The calculated values of the HOMO-LUMO energy gap shows that a charge transfer occurs within the molecule.

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Authors and Affiliations

  1. X-ray Crystallography Laboratory, Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, India

    S. Sharma, R. Kant & V. K. Gupta

  2. Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan, West Bengal, India

    G. Brahmachari

  3. Department of Physics, University of Lucknow, Lucknow, U.P., India

    A. Kumar & N. Misra

Authors
  1. S. Sharma
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  2. G. Brahmachari
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  3. A. Kumar
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  4. N. Misra
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  5. R. Kant
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  6. V. K. Gupta
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Correspondence to V. K. Gupta.

Additional information

Original Russian Text © 2018 S. Sharma, G. Brahmachari, A. Kumar, N. Misra, R. Kant, V. K. Gupta.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 59, No. 1, pp. 237–246, January–February, 2018.

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Sharma, S., Brahmachari, G., Kumar, A. et al. Molecular Modeling, Spectroscopic Investigations, and Computational Studies of DMSO solvated 7′-amino-1′,3′-dimethyl-2,2′,4′-trioxo-1′,2′,3′,4′,4a′,8a′-tetrahydrospiro[indoline-3,5′-pyrano[2,3-d]pyrimidine]-6′-carbonitrile. J Struct Chem 59, 235–244 (2018). https://doi.org/10.1134/S0022476618010389

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