Hydrogen bonds in quinoline N-oxide derivatives: first-principle molecular dynamics and metadynamics ground state study

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• 作者：Jarosław J. Panek ; Kacper Błaziak ; Aneta Jezierska
• 关键词：Quinoline N ; oxide derivatives ; Intramolecular hydrogen bond ; CPMD ; DFT ; D2 ; Metadynamics
• 刊名：Structural Chemistry
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：27
• 期：1
• 页码：65-75
• 全文大小：2,474 KB
• 参考文献：1.Car R, Parrinello M (1985) Phys Rev Lett 55:2471–2474CrossRef
  2.Laio A, Parrinello M (2002) Proc Natl Acad Sci USA 99:12562–12566CrossRef
  3.Gilli P, Ferretti V, Bertolasi V, Gilli G (1994) J Am Chem Soc 111:1023–1028CrossRef
  4.Chou P-T, Chen Y-C, Yu W-S, Chou Y-H, Wei C-Y, Cheng Y-M (2001) J Phys Chem A 105:1731–1740CrossRef
  5.Joshi NK, Joshi HC, Gahlaut R, Tewari N, Rautela R, Pant S (2012) J Phys Chem A 116:7272–7278CrossRef
  6.Paul BK, Guchhait N (2011) J Lumin 131:1918–1926CrossRef
  7.Bader RFW (1991) Chem Rev 91:893–928CrossRef
  8.Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899–926CrossRef
  9.Chung M-W, Lin T-Y, Hsieh C-C, Tang K-C, Fu H, Chou P-T, Yang S-H, Chi Y (2010) J Phys Chem A 114:7886–7891CrossRef
  10.Zhou C-H, Zhao X (2011) J Organomet Chem 696:3322–3327CrossRef
  11.Suzuki T, Fukazawa N, San-nohe K, Sato W, Yano O, Tsuruo T (1997) J Med Chem 40:2047–2052CrossRef
  12.Zhao G-J, Han K-L (2012) Acc Chem Res 45:404–413CrossRef
  13.Desiderato R, Terry JC, Freeman GR, Levy HA (1971) Acta Cryst 27:2443–2447CrossRef
  14.Steiner T, Schreurs AMM, Lutz M, Kroon J (2000) Acta Cryst C56:577–579
  15.Koshimura S, Hamada A, Otaki T, Degucki K (1954) Ann Rept Res Inst Tuberc 12:9
  16.Sakai S, Minoda K, Saito G, Akagi S, Ueno A, Fukuoka F (1955) Gann 46:605–615
  17.Steiner T (1997) Chem Commun 8:727–734CrossRef
  18.Stare J, Mavri J, Ambrožič G, Hadži D (2000) Theochem 500:429–440CrossRef
  19.Dopieralski PD, Latajka Z, Olovsson I (2009) Chem Phys Lett 476:223–226CrossRef
  20.Schlegel HB (1984) Theor Chim Acta 66:333–340CrossRef
  21.Perdew JP, Burke K, Ernzerhof M (1996) Phys Rev Lett 77:3865–3868CrossRef
  22.Kittel C (1996) Introduction to Solid State Physics, 7th edn. New York, Wiley
  23.Trouiller N, Martins JS (1991) Phys Rev B 43:1993–2006CrossRef
  24.Hockney RW (1970) Methods Comput Phys 9:136–211
  25.Nosé S (1984) Mol Phys 52:255–268CrossRef
  26.Nosé S (1984) J Chem Phys 81:511–519CrossRef
  27.Hoover WG (1985) Phys Rev A 31:1695–1697CrossRef
  28.Grimme S (2006) J Comp Chem 27:1787–1799CrossRef
  29.Iannuzzi M, Laio A, Parrinello M (2003) Phys Rev Lett 90:238302
  30.CPMD, Copyright IBM Corp., Zurich, Switzerland, 1990–2004; Copyright MPI fuer Festkoerperforschung Stuttgart, Stuttgart. Germany, 1997–2001
  31.Humphrey W, Dalke A, Schulten K (1996) J Mol Graph 14:33–38CrossRef
  32.T. Williams, C. Kelley, Gnuplot 4.0, (http://​www.​gnuplot.​info ) Copyright 1986–1993, 1998, 2004, 2007
  33.Allen MP, Tildesley DJ (1994) Computer Simulation of Liquids. Clarendon Press, Oxford
  34.Dziembowska T, Szafran M, Jagodzińska E, Natkaniec I, Pawlukojć A, Kwiatkowski JS, Baran J (2003) Spectrochim Acta Part A 59:2175–2189CrossRef
  35.Spanget-Larsen J, Hansen BKV, Hansen PE (2011) Chem Phys 389:107–115CrossRef
  36.Dziembowska T, Szafran M (1974) Rocz Chem Ann Soc Chim Polonorum 48:1687–1696
  37.Gaigeot M-P, Sprik M (2003) J Phys Chem B 107:10344–10358CrossRef
  38.Hansen PE, Spanget-Larsen J (2012) J Mol Struct 1018:8–13CrossRef
  39.Volkert LG, Conrad M (1998) J Theor Biol 193:287–306CrossRef
  40.Ghersetti S, Giorgianni S, Minari M, Spunta G (1973) Spectrosc Lett 6:167–176CrossRef
  41.Brela MZ, Wójcik MJ, Boczar M, Hashim R (2013) Chem Phys Lett 558:88–92CrossRef
  42.Denisov GS, Mavri J, Sobczyk L (2006) In: Grabowski SJ (ed) Hydrogen Bonding—New Insights. Springer, Dordrecht, pp 377–416CrossRef
  43.Jezierska A, Panek JJ, Koll A, Mavri J (2007) J Chem Phys 126:205101CrossRef
  44.Jezierska A, Panek JJ (2008) J Chem Theory Comput 4:375–384CrossRef
  45.Brela M, Stare J, Pirc G, Sollner-Dolenc M, Boczar M, Wójcik MJ, Mavri J (2012) J Phys Chem B 116:4510–4518CrossRef
  
• 作者单位：Jarosław J. Panek (1)
  Kacper Błaziak (1) (2)
  Aneta Jezierska (1)
  
  1. Faculty of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland
  2. Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224, Warsaw, Poland
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Physical Chemistry
  Theoretical and Computational Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-9001

文摘

Car–Parrinello molecular dynamics simulations were carried out for 8-hydroxyquinoline N-oxide (1) and 2-carboxyquinoline N-oxide (2) in vacuo and in the solid state. The first-principle approach was employed to intramolecular hydrogen bond features present in the studied quinoline N-oxides. Grimme’s dispersion correction was employed throughout the study. Special attention was devoted to the solid-state computations knowing that in the molecular crystals, strong and weak interactions are responsible for spatial organization and molecular properties of molecules. On the basis of Car–Parrinello molecular dynamics, it was possible to reproduce the hydrogen bond dynamics as well as to investigate the vibrational features on the basis of Fourier transform of the atomic velocity autocorrelation function. The free energy surfaces for proton motion were reproduced by unconstrained CPMD runs as well as by metadynamics. Larger flexibility of the bridge proton in 2 was noticed. The computations are verified by experimental X-ray and IR data available. Keywords Quinoline N-oxide derivatives Intramolecular hydrogen bond CPMD DFT-D2 Metadynamics