Влияние водородной связи и перехода протона в комплексах фосфорноватистых кислот на химические сдвиги в спектрах ЯМР31P

[1] J. J. Dannenberg, “An Introduction to Hydrogen Bonding", Oxford University Press, 1998.
[2] G. A. Jeffrey and W. Saenger, "Hydrogen Bonding in Biological Structures". Berlin,
Heidelberg: Springer Berlin Heidelberg, 1991.
[3] D.-W. Zhang, H. Wang and Z.-T. Li, “Hydrogen Bonding Motifs: New Progresses,” 2015.
[4] B. Jović, A. Nikolić, E. Davidović, and S. Petrović, “N-H-O hydrogen bonding. An FT‒IR,
NIR study of TV-methylformamide-ether systems,” J. Serbian Chem. Soc., vol. 75, no. 2, pp.
157–163, 2010.
[5] E. Y. Tupikina, G. S. Denisov, and P. M. Tolstoy, “NMR Study of CHN Hydrogen Bond and
Proton Transfer in 1,1-Dinitroethane Complex with 2,4,6-Trimethylpyridine,” J. Phys. Chem.
A, vol. 119, no. 4, pp. 659–668, 2015.
[6] O. Kuhl, "Phosphorus‒31 NMR spectroscopy: a concise introduction for the synthetic organic
and organometallic chemist", Springer Science & Business Media, 2008.
[7] L. D. Quin and A. J. Williams, "P‒31 NMR Spectra and Computer Assisted Structure
Verification", Advanced Chemistry Development, 2004.
[8] A. R. Barron, “P‒31 NMR Spectroscopy ”, OpenStax-CNX, pp. 1–11, 2013.
[9] I. G. Shenderovich, H.-H. Limbach, S. N. Smirnov, P. M. Tolstoy, G. S. Denisov, and N. S.
Golubev, “H/D isotope effects on the low-temperature NMR parameters and hydrogen bond
geometries of (FH) 2F−and (FH)3F−dissolved in CDF3/CDF2Cl,” Phys. Chem. Chem. Phys., vol.
4, no. 22, pp. 5488–5497, 2002.
[10] A. D. Becke, “Density‐functional thermochemistry. III. The role of exact exchange,” J. Chem.
Phys., vol. 98, no. 7, pp. 5648–5652, 1993.
[11] C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy
formula into a functional of the electron density,” Phys. Rev. B, vol. 37, no. 2, pp. 785–789,
1988.
[12] P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, “Ab Initio Calculation of
Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force
Fields,” vol. 98, no. 45, pp. 11623‒11627, 1994.
[13] M. Collinsova and J. Jiracek, “Phosphinic Acid Compounds in Biochemistry, Biology and
Medicine,” Curr. Med. Chem., vol. 7, no. 6, pp. 629–647, 2000.61
[14] J. E. Quinn, K. H. Soldenhoff, G. W. Stevens, and N. A. Lengkeek, “Solvent extraction of rare
earth elements using phosphonic/phosphinic acid mixtures,” Hydrometallurgy, vol. 157, pp.
298–305, 2015.
[15] D. Lide, “Dissociation constants of organic acids and bases,” CRC Handb. Chem. Physics, pp.
42–51, 2005.
[16] P. V. Ioannou, “Dimethylphosphinato and dimethylarsinato complexes of Sb(III) and Bi(III)
and their chemistry,” Monatshefte für Chemie - Chem. Mon., vol. 143, no. 10, pp. 1349–1356,
2012.
[17] R. A. Burrow, D. H. Farrar, A. J. Lough, M. R. Siqueira, and F. Squizani, “Phenylphosphinic
acid,” Acta Crystallogr. C., vol. 56, no. 8, pp. 357–358, 2000.
[18] S. Hossain, S. K. Gupta, and R. Murugavel, “2,6-Dimethylphenol derived H-phosphonate and
α-hydroxyphosphonate: facile synthesis, crystal chemistry, supramolecular association and
metal complexation,” CrystEngComm, vol. 17, no. 23, pp. 4355–4366, 2015.
[19] R.E. Asfin, G.S. Denisov, and K.B. Tokhadze, “The infrared spectra and enthalpies of strongly
bound dimers of phosphinic acids in the gas phase. (CH2Cl)2POOH and (C6H5)2POOH,” J.
Mol. Struct., vol. 608, no. 2, pp. 161–168, 2002.
[20] R. E. Asfin, G. S. Denisov, and K. G. Tokhadze, “The ν(OH/OD) band shape of strong
hydrogen bonded dimers of phosphinic acids. Phenomenology and formation models,” J. Mol.
Struct., vol. 790, no. 1–3, pp. 11–17, 2006.
[21] C. Detering, P. M. Tolstoy, N. S. Golubev, G. S. Denisov, and H.-H. Limbach, “Vicinal H/D
Isotope Effects in NMR Spectra of Complexes with Coupled Hydrogen Bonds: Phosphoric
Acids,” Dokl. Phys. Chem., vol. 379, no. 3, pp. 191–193, 2001.
[22] I. G. Shenderovich, A. P. Burtsev, G. S. Denisov, N. S. Golubev, and H. Limbach, “Influence
of the temperature-dependent dielectric constant on the H/D isotope effects on the NMR
chemical shifts and the hydrogen bond geometry of the collidine – HF complex in CDF3/
CDClF2 solution,” Magn. Reson. Chem., vol. 39, pp. 91–99, 2001.
[23] P. M. Tolstoy, P. Schah-Mohammedi, S. N. Smirnov, N. S. Golubev, G. S. Denisov, and H. H.
Limbach, “Characterization of Fluxional Hydrogen-Bonded Complexes of Acetic Acid and
Acetate by NMR: Geometries and Isotope and Solvent Effects,” J. Am. Chem. Soc., vol. 126,
no. 17, pp. 5621–5634, 2004.
[24] H.-H. Limbach, P. M. Tolstoy, N. Pérez-Hernández, J. Guo, I. G. Shenderovich, and G. S.62
Denisov, “OHO Hydrogen Bond Geometries and NMR Chemical Shifts: From Equilibrium
Structures to Geometric H/D Isotope Effects, with Applications for Water, Protonated Water,
and Compressed Ice,” Isr. J. Chem., vol. 49, no. 2, pp. 199–216, 2009.
[25] L. Gonzalez, O. Mo, M. Yanez, J. Elguero, “Very strong hydrogen bonds in neutral molecules:
The phosphinic acid dimers,” J. Chem. Phys., vol. 109, no. 7, pp. 2685–2693, 1998.
[26] N. S. Golubev, R. E. Asfin, S. N. Smirnov, P. M. Tolstoi, “Study of hydrogen bonds of
hypophosphorous acid by 1H, 2H, 31P, and 15N NMR spectroscopy under slow exchange
conditions” Russ. J. Gen. Chem., vol. 76, no. 6, pp. 915–924, 2006.
[27] G. Begimova, E. Y. Tupikina, V. K. Yu, G. S. Denisov, M. Bodensteiner, and I. G.
Shenderovich, “Effect of Hydrogen Bonding to Water on the 31 P Chemical Shift Tensor of
Phenyl- and Trialkylphosphine Oxides and α-Amino Phosphonates,” J. Phys. Chem. C, vol.
120, no. 16, pp. 8717–8729, 2016.
[28] P. M. Tolstoy, J. Guo, B. Koeppe, N. S. Golubev, G. S. Denisov, S. N. Smirnov,. H.-H.
Limbach, “Geometries and tautomerism of OHN hydrogen bonds in aprotic solution probed by
H/D isotope effects on 13C NMR chemical shifts,” J. Phys. Chem. A, vol. 114, no. 40, pp.
10775–10782, 2010.
[29] S. N. Smirnov, N. S. Golubev, G. S. Denisov, H. Benedict, P. Schah-mohammedi, and H.
Limbach, “Hydrogen/Deuterium Isotope Effects on the NMR Chemical Shifts and Geometries
of Intermolecular Low-Barrier Hydrogen-Bonded Complexes,” J. Am. Chem. Soc., vol. 7863,
no. 6, pp. 4094–4101, 1996.
[30] H.-H. Limbach, M. Pietrzak, S. Sharif, P. M. Tolstoy, I. G. Shenderovich, S. N. Smirnov, N. S.
Golubev, G. S. Denisov, “NMR parameters and geometries of OHN and ODN hydrogen bonds
of pyridine-acid complexes,” Chem. Eur. J., vol. 10, no. 20, pp. 5195–5204, 2004.
[31] P. M. Tolstoy, S. N. Smirnov, I. G. Shenderovich, N. S. Golubev, G. S. Denisov, and H.-H.
Limbach, “NMR studies of solid state—solvent and H/D isotope effects on hydrogen bond
geometries of 1:1 complexes of collidine with carboxylic acids,” J. Mol. Struct., vol. 700, no.
1–3, pp. 19–27, 2004.
[32] T. Steiner, “Lengthening of the Covalent X−H Bond in Heteronuclear Hydrogen Bonds
Quantified from Organic and Organometallic Neutron Crystal Structures,” J. Phys. Chem. A,
vol. 102, no. 35, pp. 7041–7052, 1998.
[33] D. V. Andreeva, B. Ip, A. A. Gurinov, P. M. Tolstoy, G. S. Denisov, I. G. Shenderovich, H.-
H. Limbach, “Geometrical features of hydrogen bonded complexes involving sterically63
hindered pyridines,” J. Phys. Chem. A, vol. 110, no. 37, pp. 10872–10879, 2006.
[34] I. G. Shenderovich, P. M. Tolstoy, N. S. Golubev, S. N. Smirnov, G. S. Denisov, H. H.
Limbach, “Low-temperature NMR studies of the structure and dynamics of a novel series of
acid-base complexes of HF with collidine exhibiting scalar couplings across hydrogen bonds,”
J. Am. Chem. Soc., vol. 125, no. 38, pp. 11710–11720, 2003.
[35] S. S. Batsanov, “Van der Waals Radii of Elements,” Inorg. Mater. Transl. from Neorg. Mater.
Orig. Russ. Text, vol. 37, no. 9, pp. 871–885, 2001.
[36] A. Bondi, “van der Waals Volumes and Radii,” J. Phys. Chem., vol. 68, no. 3, pp. 441–451,
1964.
[37] E. Arunan, G.R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner, I. Alkorta, D. C. Clary, R. H.
Crabtree, J. J. Dannenberg, P. Hobza, H.G. Kjaergaard., A. C. Legon, B. Mennucci, D. J.
Nesbitt, “Definition of the hydrogen bond (IUPAC Recommendations 2011),” Pure Appl.
Chem, vol. 83, no. 8, pp. 1637–1641, 2011
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