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Pure Appl. Chem., 2009, Vol. 81, No. 4, pp. 571-583

http://dx.doi.org/10.1351/PAC-CON-08-08-14

Symmetry of hydrogen bonds in solution

Charles L. Perrin

Department of Chemistry, University of California, San Diego, La Jolla, CA 92093-0358, USA

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  • Kawashima Yukio, Tachikawa Masanori: Ab Initio Path Integral Molecular Dynamics Study of the Nuclear Quantum Effect on Out-of-Plane Ring Deformation of Hydrogen Maleate Anion. J. Chem. Theory Comput. 2014, 10, 153. <http://dx.doi.org/10.1021/ct4007986>
  • Kawashima Yukio, Tachikawa Masanori: Nuclear quantum effect on intramolecular hydrogen bond of hydrogen maleate anion: An ab initio path integral molecular dynamics study. Chemical Physics Letters 2013, 571, 23. <http://dx.doi.org/10.1016/j.cplett.2013.03.080>
  • Carlsson Anna-Carin C., Uhrbom Martin, Karim Alavi, Brath Ulrika, Gräfenstein Jürgen, Erdélyi Máté: Solvent effects on halogen bond symmetry. CrystEngComm 2013, 15, 3087. <http://dx.doi.org/10.1039/c2ce26745d>
  • Oliveira Boaz Galdino de: Structure, energy, vibrational spectrum, and Bader's analysis of π⋯H hydrogen bonds and H−δ⋯H+δ dihydrogen bonds. Phys. Chem. Chem. Phys. 2013, 15, 37. <http://dx.doi.org/10.1039/c2cp41749a>
  • Ogata Yudai, Daido Masashi, Kawashima Yukio, Tachikawa Masanori: Nuclear quantum effects on protonated lysine with an asymmetric low barrier hydrogen bond: an ab initio path integral molecular dynamics study. RSC Adv. 2013, 3, 25252. <http://dx.doi.org/10.1039/c3ra44077j>
  • Galer Petra, Golobič Amalija, Koller Jože, Košmrlj Berta, Šket Boris: Structures in solid state and solution of dimethoxy curcuminoids: regioselective bromination and chlorination. Chemistry Central Journal 2013, 7, 107. <http://dx.doi.org/10.1186/1752-153X-7-107>
  • Oishi Shunsuke, Saito Susumu: Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives. Angew. Chem. 2012, 124, 5491. <http://dx.doi.org/10.1002/ange.201200304>
  • Oishi Shunsuke, Saito Susumu: Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives. Angew. Chem. Int. Ed. 2012, 51, 5395. <http://dx.doi.org/10.1002/anie.201200304>
  • Perrin Charles L., Karri Phaneendrasai, Moore Curtis, Rheingold Arnold L.: Hydrogen-Bond Symmetry in Difluoromaleate Monoanion. S J Am Chem Soc 2012, 134, 7766. <http://dx.doi.org/10.1021/ja2117848>
  • Carlsson Anna-Carin C., Gräfenstein Jürgen, Budnjo Adnan, Laurila Jesse L., Bergquist Jonas, Karim Alavi, Kleinmaier Roland, Brath Ulrika, Erdélyi Máté: Symmetric Halogen Bonding Is Preferred in Solution. S J Am Chem Soc 2012, 134, 5706. <http://dx.doi.org/10.1021/ja301341h>
  • Carlsson Anna-Carin C., Gräfenstein Jürgen, Laurila Jesse L., Bergquist Jonas, Erdélyi Máté: Symmetry of [N–X–N]+ halogen bonds in solution. Chem Commn 2012, 48, 1458. <http://dx.doi.org/10.1039/c1cc15839b>
  • Dopieralski Przemyslaw, Perrin Charles L., Latajka Zdzislaw: On the Intramolecular Hydrogen Bond in Solution: Car–Parrinello and Path Integral Molecular Dynamics Perspective. J Chem Theory and Comput 2011, 7, 3505. <http://dx.doi.org/10.1021/ct200580c>
  • Bogle Xavier S., Singleton Daniel A.: Isotope-Induced Desymmetrization Can Mimic Isotopic Perturbation of Equilibria. On the Symmetry of Bromonium Ions and Hydrogen Bonds. S J Am Chem Soc 2011, 133, 17172. <http://dx.doi.org/10.1021/ja2084288>
  • Kong S., Borissova A. O., Lesnichin S. B., Hartl M., Daemen L. L., Eckert J., Antipin M. Yu., Shenderovich I. G.: Geometry and Spectral Properties of the Protonated Homodimer of Pyridine in the Liquid and Solid States. A Combined NMR, X-ray Diffraction and Inelastic Neutron Scattering Study. J Phys Chem A 2011, 115, 8041. <http://dx.doi.org/10.1021/jp203543g>
  • Perrin Charles L., Karri Phaneendrasai: Are there single-well hydrogen bonds in pyridine–dichloroacetic acid complexes?. Chem Commun 2010, 46, 481. <http://dx.doi.org/10.1039/b917765e>
  • Lesnichin Stepan B., Tolstoy Peter M., Limbach Hans-Heinrich, Shenderovich Ilja G.: Counteranion-dependent mechanisms of intramolecular proton transfer in aprotic solution. Phys Chem Chem Phys 2010, 12, 10373. <http://dx.doi.org/10.1039/c004499g>
  • Perrin Charles L.: ChemInform Abstract: Symmetry of Hydrogen Bonds in Solution. ChemInform 2009, 40. <http://dx.doi.org/10.1002/chin.200928278>
  • Perrin Charles L., Lau Jonathan S., Kim Yeong-Joon, Karri Phaneendrasai, Moore Curtis, Rheingold Arnold L.: Asymmetry of the “Strongest” OHO Hydrogen Bond, in the Monoanion of (±)-α,α′-Di-tert-butylsuccinate. J Am Chem Soc 2009, 131, 13548. <http://dx.doi.org/10.1021/ja905806h>