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The ionic hydrogen bond and ion solvation. 3. Bonds involving cyanides. Correlations with proton affinities

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    The ionic hydrogen bond and ion solvation. 3. Bonds involving cyanides. Correlations with proton affinities
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    The Journal of Physical Chemistry

    Cite this: J. Phys. Chem. 1985, 89, 24, 5217–5222
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    https://doi.org/10.1021/j100270a020
    Published November 1, 1985
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    This article is cited by 37 publications.

    1. Laura J. Haupert and Paul G. Wenthold . Hydration Energies of Aromatic Ions in the Gas Phase. The Journal of Physical Chemistry A 2013, 117 (6) , 1164-1170. https://doi.org/10.1021/jp305119y
    2. Michael Meot-Ner (Mautner) . Update 1 of: Strong Ionic Hydrogen Bonds. Chemical Reviews 2012, 112 (10) , PR22-PR103. https://doi.org/10.1021/cr200430n
    3. Sehan Lee, Kwang-Hwi Cho, Chang Joon Lee, Go Eun Kim, Chul Hee Na, Youngyong In, and Kyoung Tai No . Calculation of the Solvation Free Energy of Neutral and Ionic Molecules in Diverse Solvents. Journal of Chemical Information and Modeling 2011, 51 (1) , 105-114. https://doi.org/10.1021/ci100299m
    4. William A. Donald and Evan R. Williams. An Improved Cluster Pair Correlation Method for Obtaining the Absolute Proton Hydration Energy and Enthalpy Evaluated with an Expanded Data Set. The Journal of Physical Chemistry B 2010, 114 (41) , 13189-13200. https://doi.org/10.1021/jp1068945
    5. Steen Hammerum. Alkyl Radicals as Hydrogen Bond Acceptors: Computational Evidence. Journal of the American Chemical Society 2009, 131 (24) , 8627-8635. https://doi.org/10.1021/ja901854t
    6. Michael B. Burt and, Travis D. Fridgen. Heterogeneous Proton-Bound Dimers with a High Dipole Moment Monomer:  How Could We Experimentally Observe These Anomalous Ionic Hydrogen Bonds?. The Journal of Physical Chemistry A 2007, 111 (42) , 10738-10744. https://doi.org/10.1021/jp075086y
    7. Travis D. Fridgen. Structures of Heterogeneous Proton-Bond Dimers with a High Dipole Moment Monomer:  Covalent vs Electrostatic Interactions. The Journal of Physical Chemistry A 2006, 110 (18) , 6122-6128. https://doi.org/10.1021/jp057335t
    8. Michael Meot-Ner (Mautner) . The Ionic Hydrogen Bond. Chemical Reviews 2005, 105 (1) , 213-284. https://doi.org/10.1021/cr9411785
    9. Asit K. Chandra and, Thérèse Zeegers-Huyskens. Theoretical Study of the Symmetry of the (OH···O)- Hydrogen Bonds in Vinyl Alcohol−Vinyl Alcoholate Systems. The Journal of Organic Chemistry 2003, 68 (9) , 3618-3625. https://doi.org/10.1021/jo020735h
    10. Matthias Witt, Hans-Friedrich Grützmacher. Proton bound homodimers and heterodimers of amides and amines in the gas phase. Equilibrium studies by Fourier transform ion cyclotron resonance spectrometry. Journal of the American Society for Mass Spectrometry 2002, 13 (11) , 1273-1281. https://doi.org/10.1016/S1044-0305(02)00457-9
    11. Travis D. Fridgen and, Terry B. McMahon. Binding Energies of Proton-Bound Ether/Alcohol Mixed Dimers Determined by FTICR Radiative Association Kinetics Measurements. The Journal of Physical Chemistry A 2002, 106 (8) , 1576-1583. https://doi.org/10.1021/jp0137569
    12. Thérèse Zeegers-Huyskens. Are the Enol−Enolate Hydrogen Bonds at Matched PA Really Symmetrical?. The Journal of Organic Chemistry 1999, 64 (13) , 4946-4948. https://doi.org/10.1021/jo982395z
    13. Michael Meot-Ner (Mautner),, L. Wayne Sieck,, Kristin K. Koretke, and, Carol A. Deakyne. The Carbon Lone Pair as Electron Donor. Ionic Hydrogen Bonds in Isocyanides. Journal of the American Chemical Society 1997, 119 (43) , 10430-10438. https://doi.org/10.1021/ja960669z
    14. Mehvish Mumtaz, Nazim Hussain, Sidra Salam, Muhammad Bilal. Multifunctional nanodiamonds as emerging platforms for cancer treatment, and targeted delivery of genetic factors and protein medications—a review. Journal of Materials Science 2022, 57 (17) , 8064-8099. https://doi.org/10.1007/s10853-022-07168-x
    15. Guy Bouchoux. Gas phase basicities of polyfunctional molecules. Part 6: Cyanides and isocyanides. Mass Spectrometry Reviews 2018, 37 (4) , 533-564. https://doi.org/10.1002/mas.21538
    16. . Gas‐Phase Cation Affinity and Basicity Scales. 2009, 323-399. https://doi.org/10.1002/9780470681909.ch6
    17. Rafael A. Shimkunas, Erik Robinson, Robert Lam, Steven Lu, Xiaoyang Xu, Xue-Qing Zhang, Houjin Huang, Eiji Osawa, Dean Ho. Nanodiamond–insulin complexes as pH-dependent protein delivery vehicles. Biomaterials 2009, 30 (29) , 5720-5728. https://doi.org/10.1016/j.biomaterials.2009.07.004
    18. Aliouane Akrour, Zohra Chikh, Fayçal Djazi, Mostapha Elbannay, Florence Berruyer, Guy Bouchoux. Gas phase protonation of α, β and γ-dicarbonyls: Thermochemistry and structures. International Journal of Mass Spectrometry 2007, 267 (1-3) , 63-80. https://doi.org/10.1016/j.ijms.2007.02.020
    19. Paola Gilli, Loretta Pretto, Gastone Gilli. PA/pKa equalization and the prediction of the hydrogen-bond strength: A synergism of classical thermodynamics and structural crystallography. Journal of Molecular Structure 2007, 844-845 , 328-339. https://doi.org/10.1016/j.molstruc.2007.05.014
    20. Guy Bouchoux. Gas‐phase basicities of polyfunctional molecules. Part 1: Theory and methods. Mass Spectrometry Reviews 2007, 26 (6) , 775-835. https://doi.org/10.1002/mas.20151
    21. Jean-François Gal, Pierre-Charles Maria. Correlation Analysis of Acidity and Basicity: From the Solution to the Gas Phase. 2007, 159-238. https://doi.org/10.1002/9780470171967.ch6
    22. Asit K. Chandra, Thérèse Zeegers-Huyskens. Theoretical Study of (CH···C) - Hydrogen Bonds in CH 4- n X n (X = F, Cl; n = 0, 1, 2) Systems Complexed with Their Homoconjugate and Heteroconjugate Carbanions. The Journal of Physical Chemistry A 2005, 109 (51) , 12006-12013. https://doi.org/10.1021/jp054123n
    23. Asit K. Chandra, Thérèse Zeegers-Huyskens. Theoretical study of (XYO⋯H⋯OXY)+ (X, Y=H, F, Cl) systems. From the asymmetrical to the symmetrical (O⋯H⋯O)+ hydrogen bonds. Journal of Molecular Structure 2004, 706 (1-3) , 75-83. https://doi.org/10.1016/j.molstruc.2004.02.053
    24. Li Bian. Proton Donor Is More Important Than Proton Acceptor in Hydrogen Bond Formation:  A Universal Equation for Calculation of Hydrogen Bond Strength. The Journal of Physical Chemistry A 2003, 107 (51) , 11517-11524. https://doi.org/10.1021/jp035446r
    25. A.K Chandra, M.T Nguyen, Th Zeegers-Huyskens. Theoretical study of the protonation and deprotonation of cytosine. Implications for the interaction of cytosine with water. Journal of Molecular Structure 2000, 519 (1-3) , 1-11. https://doi.org/10.1016/S0022-2860(99)00276-8
    26. Ben L.M. Van Baar. Chapter 2. Ionisation Methods in LC-MS and LC-MS-MS (TSP, APCI, ESP and cf-FAB). 1996, 71-133. https://doi.org/10.1016/S0301-4770(08)60779-4
    27. Thérèse Zeegers-Huyskens. Correlation between the frequency shift of the stretching vibration of hydrogen bond complexes and the proton affinity. Journal of Molecular Liquids 1995, 67 , 33-47. https://doi.org/10.1016/0167-7322(95)00864-0
    28. Jin Yong Lee, Sang Joo Lee, Hyuk Soon Choi, Seung Joo Cho, Kwang Soo Kim, Tae-Kyu Ha. Ab initio study of the complexation of benzene with ammonium cations. Chemical Physics Letters 1995, 232 (1-2) , 67-71. https://doi.org/10.1016/0009-2614(94)01330-X
    29. Carol A. Deakyne, Dawn M. Knuth, Carlos V. Speller, Michael Meot-Ner (Mautner), L.Wayne Sieck. Filling of solvent shells about ions. Journal of Molecular Structure: THEOCHEM 1994, 307 , 217-238. https://doi.org/10.1016/0166-1280(94)80130-4
    30. A. A. Voityuk, A. A. Bliznyuk. Quantum chemical study of molecular ion complexes with hydrogen bonds (Review). Journal of Structural Chemistry 1993, 33 (6) , 899-924. https://doi.org/10.1007/BF00745613
    31. V. V. Vasilyev, A. A. Bliznyuk, A. A. Voityuk. A combined quantum chemical/molecular mechanical study of hydrogen‐bonded systems. International Journal of Quantum Chemistry 1992, 44 (5) , 897-930. https://doi.org/10.1002/qua.560440517
    32. M. Alcamí, O. Mó, M. Yáñez. Ab initio molecular orbital treatment of hydroxylamine-X+-water and hydroxylamine-X+-ammonia (X = H, Li) clusters. Chemical Physics 1991, 151 (1) , 21-36. https://doi.org/10.1016/0301-0104(91)80003-Z
    33. Zofia Dega-Szafran, Andrzej Hrynio, Miroslaw Szafran. A quantitative comparison of spectroscopic and energy data, in solution, of NHO and OHO hydrogen bonds and gas-phase proton affinities: complexes of pyridines and pyridine N-oxides with acetic acids. Journal of Molecular Structure 1990, 240 , 159-174. https://doi.org/10.1016/0022-2860(90)80507-G
    34. Thérèse Zeegers-Huyskens. Importance of the proton affinities in hydrogen bond studies. A new exponential expression. Journal of Molecular Structure 1988, 177 , 125-141. https://doi.org/10.1016/0022-2860(88)80083-8
    35. M.F.A. Dove. The Halogens and hydrogen. Coordination Chemistry Reviews 1988, 85 , 504-522. https://doi.org/10.1016/0010-8545(88)85031-8
    36. Th. Zeegers-Huyskens. Energies of OH⋯X− hydrogen bonds in the gas phase and proton affinities. Chemical Physics Letters 1986, 129 (2) , 172-175. https://doi.org/10.1016/0009-2614(86)80191-9
    37. C. V. SPELLER, M. MEOT‐NER. ChemInform Abstract: The Ionic Hydrogen Bond and Ion Solvation. Part 3. Bonds Involving Cyanides. Correlations with Proton Affinities. Chemischer Informationsdienst 1986, 17 (11) https://doi.org/10.1002/chin.198611071
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    Cite this: J. Phys. Chem. 1985, 89, 24, 5217–5222
    Click to copy citationCitation copied!
    https://doi.org/10.1021/j100270a020
    Published November 1, 1985
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