Hydrogen bridges of polycyclic aromatic systems with O-H···O bonds — a gas-phase vs. solid-state Car-Parrinello study

Journal of Molecular Modeling - Tập 21 - Trang 1-7 - 2015
Jarosław J. Panek1, Aneta Jezierska1
1Faculty of Chemistry, University of Wrocław, Wrocław, Poland

Tóm tắt

The current study belongs to a series of investigations of polycyclic aromatic compounds containing intramolecular hydrogen bonds. Close proximity of the coupled aromatic system and hydrogen bridges gives rise to resonance-assisted hydrogen bonding phenomena. Substituted naphthols are ideally suited for this kind of investigation. The parent compound, 1-hydroxy-8-methoxy-3-methylnaphthalene, and its derivative, 1-bromo-5-hydroxy-4-isopropoxy-7-methylnaphthalene, both with known crystal structure, are investigated. Car-Parrinello molecular dynamics (CPMD) is chosen as a theoretical background for this study. Gas phase and solid state simulations are carried out. The effect of Grimme’s dispersion corrections is also included. The report presents time evolution of structural parameters, spectroscopic signatures based on the CPMD simulations, and comparison with available experimental data. We show that the proton transfer phenomena do not occur within the simulations, which is consistent with evaluation based on the acidity of the donor and acceptor sites. The effects of the substitution in the aromatic system and change of the environment (gas vs. condensed phase) are of similar magnitude.

Tài liệu tham khảo

Grabowski S (2006) Hydrogen bonding—new insights. Challenges and advances in computational chemistry and physics 3. Springer, Dordrecht Sobczyk L, Grabowski SJ, Krygowski TM (2005) Interrelation between H-bond and Pi-electron delocalization. Chem Rev 105:3513–3560 Peters K, Peters E-M, Günther C, Bringmann G (1999) Crystal structure of 1-hydroxy-8-methoxy-3-methylnaphthalene, C10H5(OCH3)(OH)(CH3). Z Kristallogr 214:545–546 Peters K, Peters E-M, Ochse M, Bringmann G (1999) Crystal structure of 1-bromo-6-hydroxy-4-isopropoxy-8-methyl-naphthalene, C10H4(OC3H7)(OH)(CH3)Br. Z Kristallogr 214:541–542 Car R, Parrinello M (1985) Unified approach for molecular dynamics and density-functional theory. Phys Rev Lett 55:2471–2474 Jezierska A, Panek JJ, Koll A (2008) Spectroscopic properties of a strongly anharmonic Mannich base N-oxide. Chem Phys Chem 9:839–846 Jezierska-Mazzarello A, Panek JJ, Szatyłowicz H, Krygowski TM (2012) Hydrogen bonding as a modulator of aromaticity and electronic structure of selected ortho-hydroxybenzaldehyde derivatives. J Phys Chem A 116:460–475 Jezierska A, Panek JJ, Mazzarello R (2009) Structural and electronic structure differences due to the O–H···O and O–H···S bond formation in selected benzamide derivatives: a first-principles molecular dynamics study. Theor Chem Account 124:319–330 Jezierska A, Panek JJ, Koll A, Mavri J (2007) Car-Parrinello simulation of an O–H stretching envelope and potential of mean force of an intramolecular hydrogen bonded system: application to a Mannich base in solid state and in vacuum. J Chem Phys 126:205101 Gilli P, Bertolasi V, Ferretti V, Gilli G (2000) Evidence for Intramolecular N-H···O resonance-assisted hydrogen bonding in β-enaminones and related heterodienes. A combined crystal-structural, IR and NMR spectroscopic, and quantum-mechanical investigation. J Am Chem Soc 122:10405–10417 Alder RW, Bowman PS, Steele RS, Winterman DR (1968) The remarkable basicity of 1,8-bis(dimethylamino)naphthalene. Chem Commun 452:723–724 Bieńko A, Latajka Z, Sawka-Dobrowolska W, Sobczyk L, Ozeryanskii VA, Pozharskii AF, Grech E, Nowicka-Scheibe J (2003) Low barrier hydrogen bond in protonated proton sponge. X-ray diffraction, infrared, and theoretical ab initio and density functional theory studies. J Chem Phys 119:4313–4319 Staab HA, Saupe T (1988) “Proton sponges” and the geometry of hydrogen bonds: aromatic nitrogen bases with exceptional basicities. Angew Chem Int Ed Engl 27:865–879 Pozharskii AF, Ozeryanskii VA (2012) Proton sponges and hydrogen transfer phenomena. Mendeleev Commun 22:117–124 Ozeryanskii VA, Vlasenko MP, Pozharskii AF (2013) ‘Proton sponge’ amides: unusual chemistry and conversion into superbasic 6,7-bis(dimethylamino)perimidines. Tetrahedron 69:1919–1929 Boiko LZ, Sorokin VI, Filatova EA, Starikova ZA, Ozeryanskii VA, Pozharskii AF (2011) Three examples of naphthalene proton sponges with extreme or unusual structural parameters. General view on factors influencing proton sponge geometry. J Mol Struct 1005:12–16 Grimme S (2006) Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comp Chem 27:1787–1799 Hockney RW (1970) The potential calculation and some applications. Methods Comput Phys 9:136–211 Perdew JP, Burke K, Ernzerhof M (1996) Generalized gradient approximation made simple. Phys Rev Lett 77:3865–3868 Troullier N, Martins JL (1991) Efficient pseudopotentials for plane-wave calculations. Phys Rev B 43:8861–8869 Nosé S (1984) A molecular dynamics method for simulations in the canonical ensemble. Mol Phys 52:255–268 Hoover WG (1985) Canonical dynamics: equilibrium phase-space distributions. Phys Rev A 31:1695–1697 CPMD, Copyright IBM Corp., Zurich, Switzerland, 1990–2004; Copyright MPI für Festkörperforschung Stuttgart, Germany, 1997–2001 Humphrey W, Dalke A, Schulten K (1996) VMD - visual molecular dynamics. J Mol Graph 14:33–38 Broeker HB, Campbell J, Cunningham R, Denholm D, Elber G, Fearick R, Grammes C, Hart L et al. Gnuplot, Copyright (C) 1986–1993, 1998, 2004. Williams T, Kelley C; Copyright (C) 2004–2007 Hansch C, Leo A, Taft RW (1991) A survey of Hammett substituent constants and resonance and field parameters. Chem Rev 91:165–195 Krygowski TM, Szatyłowicz H, Zachara JE (2005) Molecular geometry as a source of chemical information. 5. Substituent effect on proton transfer in para-substituted phenol complexes with fluorides — a B3LYP/6-311+G** study. J Chem Inf Model 45:652–656 Gilli P, Pretto L, Bertolasi V, Gilli G (2009) Predicting hydrogen-bond strengths from acid–base molecular properties. The pKa slide rule: toward the solution of a long-lasting problem. Acc Chem Res 42:33–44 Filarowski A, Koll A, Głowiak T (2002) Low barrier hydrogen bonds in sterically modified Schiff bases. J Chem Soc Perkin Trans 2:835–842 Jezierska-Mazzarello A, Panek JJ, Vuilleumier R, Koll A, Ciccotti G (2011) Direct observation of the substitution effects on the hydrogen bridge dynamics in selected Schiff bases—a comparative molecular dynamics study. J Chem Phys 134:034308