Abstract
Within the quantum theory of atoms in molecules (QTAIM) the electronic structure of sulphoxylate acid HOSOH and compounds of a homological series of ethers of sulphoxylate acid CH3(CH2)
n
OSOH, where n ≤ 8, is studied. It is found that there is an intramolecular hydrogen bond O⋯H resulting in the formation of a cyclic structure 
. Qualitative relationships of the electronegativities of the groups χ(R) are obtained and the χ(R) scale is derived. The possibilities of predicting “structure-property” correlations are discussed.
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References
P. G. Mezey, Mol. Phys., 96, 169–178 (1999).
P. Hohenberg and W. Kohn, Phys. Rev., B136, 864–871 (1964).
H.-D. Höltje, W. Sippl, D. Rognan, and G. Folkers, Molecular Modeling: Basic Principles and Applications, 2nd ed., Wiley-VCH, Weinheim, Germany (2003).
R. F. W. Bader, Atoms in molecules. Quantum theory, Oxford University Press, Oxford (1990).
L. Pauling, Nature of the Chemical Bond, 2nd ed., Cornell University Press, Ithaca, NY (1939).
A. R. Cherkasov, V. I. Galkin, E. M. Zueva, and R. A. Cherkasov, Russ. Chem. Rev., 67, No. 5, 375–393 (1998).
V. S. Urusov, J. Struct. Chem., 35, No. 1, 101–114 (1994).
L. Komorowski, S. L. Boyd, and R. J. Boyd, J. Phys. Chem., 100, 3448–3453 (1996).
A. N. Vereshchagin, Inductive Effect [in Russian], Nauka, Moscow (1987).
S. W. Benson, Thermochemical Kinetics, Wiley, New York (1968).
V. M. Tatevskii, Quantum Mechanics and Molecular Structural Theory [in Russian], MGU, Moscow (1965).
W. H. Flygare, Molecular Structure and Dynamics, Prentice-Hall, Englewood Cliffs, NJ (1968).
A. N. Pankratov, Electronic Structure and Reactivity of Inorganic, Organic, Organoelement and Coordination Compounds: an Experience in the Area of Applied Quantum Chemistry, Nova Science Publishers, Inc., New York (2007), p. 82–89.
J. Cioslowski and S. T. Mixon, J. Am. Chem. Soc., 115, No. 3, 1084–1088 (1993).
V. V. Turovtsev, Yu. D. Orlov, and Yu. A. Lebedev, J. Phys. Chem. A, 83, No. 2, 245–253 (2009).
V. V. Turovtsev and Yu. D. Orlov, J. Phys. Chem. A, 84, No. 6, 965–970 (2010).
V. V. Turovtsev and Yu. D. Orlov, J. Phys. Chem. A, 84, No. 7, 1174–1181 (2010).
N. P. Rusakova, V. V. Turovtsev, and Yu. D. Orlov, Russ. J. Appl. Chem., 84, No. 9, 1626–1628 (2011).
N. P. Rusakova, V. V. Turovtsev, and Yu. D. Orlov, Vestn. Tver State Univ., Ser. Khimiya, No. 10, 4–8 (2010).
S. V. Makarov, D. S. Sal’nikov, and A. S. Pogorelova, Russ. J. Inorg. Chem., 55, No. 2, 301–304 (2010).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, Pople et al., Gaussian 03 (Revision E 0.1, SMP), Gaussian Inc., Pittsburgh, PA (2007).
N. P. Rusakova, V. V. Turovtsev, and Yu. D. Orlov, Vestn. Tver State Univ., Ser. Fizika, No. 6 (34), 204–209 (2007).
A. Todd, Keith AIMAll (Version 10.03.25); http://aim.tkgristmill.com (2010).
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Original Russian Text © 2015 N. P. Rusakova, V. V. Turovtsev, Yu. D. Orlov.
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Translated from Zhurnal Strukturnoi Khimii, Vol. 56, No. 1, pp. 29–33, January–February, 2015.
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Rusakova, N.P., Turovtsev, V.V. & Orlov, Y.D. Comparative analysis of the electronic structure and electronegativity of groups of unbranched ethers of sulphoxylate acid. J Struct Chem 56, 22–26 (2015). https://doi.org/10.1134/S0022476615010047
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DOI: https://doi.org/10.1134/S0022476615010047