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Hydrogen bonding motif in 2-hydroxy-1,4-naphthoquinone

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Abstract.

Self-assemblies of 2-hydroxy-1,4-naphthoquinone (HNQ) have been investigated using the (HNQ) n (n=1–4) series as modeled systems employing ab initio Hartree–Fock calculations. The energetics and charge distribution in these molecular systems are presented. As revealed from the electron density in the highest occupied molecular orbital of the lowest energy conformers of (HNQ) n (n=1–4) the charge ‘percolates’ to the end unit of the assembly. This has been supported by the molecular electrostatic potential topography.

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References

  1. Odile M, Dreyer J (1994) Biochem J 300:99

  2. Allakhverdiev SI, Karacan MS, Somer G, Karcan N, Khan EM, Rane SY, Padhye S, Kilmov VV, Renger G (1994) Biochem 33:12210

    Google Scholar 

  3. Thomson RH (1971) Naturally occurring quinones. Academic, New York

  4. Morton RA (1965) Biochemistry of quinones. Academic, New York

  5. Tanaka K, Tamamushi R, Ogawa T (1985) J Technol Biotech 35B:191

    Google Scholar 

  6. Idriss KA, Sadaira H, Hashem EY, Saleh MS, Soliman SA (1996) Monatshefte fuer Chemie 127:29

    Google Scholar 

  7. Rostkowska H, Nowak MJ, Lapinski L, Adamowicz L (1998) Spectrochim. Acta A 54:1091

  8. Dekkers J, Kooijman H, Kroon J, Grech E (1996) Acta Cryst C 52:2896

    Google Scholar 

  9. GAUSSIAN94 package: Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, Cheeseman JR, Keith T, Peterson GA, Montgomery JA, Raghavachari K, Al–laham MA, Zakrzewski VG, Oritz JV, Forseman JB, Cioslowski J, Stefanov BB, Nanayakkara A, Challacombe M, Peng CY, Ayala PY, Chen W, Wong MW, Andres JL, Replolge ES, Gomperts R, Martin RL, Fox DJ, Binkley JS, Defrees DJ, Baker J, Stewart JJP, Head–Gordon M, Gonzalez C, Pople JA (1995) GAUSSIAN Inc., Pittusburgh

  10. Limaye AC, Gadre SR (2001) Curr Sci 80:1298

  11. Gadre SR, Shrisat RN (2000) Electrostatics of atoms and molecules. Universites Press, Hyderabad, and references therein

  12. Naray-Szabo G, Ferenczy GG (1995) Chem Rev 95:829

  13. Pingale SS, Gadre SR, Bartolotti LJ (1998) J Phys Chem A 102:9987

    Google Scholar 

  14. Gadre SR, Kulkarni SA, Shivastava IA (1992) J Chem Phys 96:5253

    Google Scholar 

  15. Patai S, Rappoport Z (1988) The Chemistry of quinonoid compounds, Part 1, vol. 2. Wiley, Berlin Heidelberg New York, p. 87

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Authors and Affiliations

  1. Department of Chemistry, University of Pune, 411007, India

    N. R. Dhumal, A. V. Todkary, S. Y. Rane & S. P. Gejji

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  1. N. R. Dhumal
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  2. A. V. Todkary
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  3. S. Y. Rane
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  4. S. P. Gejji
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Correspondence to S. P. Gejji.

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Dhumal, N., Todkary, A., Rane, S. et al. Hydrogen bonding motif in 2-hydroxy-1,4-naphthoquinone. Theor Chem Acc 113, 161–166 (2005). https://doi.org/10.1007/s00214-004-0620-1

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  • DOI: https://doi.org/10.1007/s00214-004-0620-1

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