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Electrostatic forces and geometry of organic molecules. Part I. Saturated molecules with tetrahedral fragments

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Abstract

A new qualitative approach for analysis of organic molecules geometry, which can be considered as a development of known VSEPR concept is suggested. The core of the approach is electrostatic model, based on the division of the total electron density into an isotropic component which after summation with the nuclear charges turn them into point positive charges (PPCs), and an anisotropic component, tied to the local electron densities (LEDs) of chemical bonds and lone pairs of electrons (LPs). Electrostatic forces (ESFs) affecting the LEDs and PPCs in typical tetrahedral molecular fragments with central carbon atom or heteroatom are considered in detail. The procedure of conditional fixation of PPCs followed by evaluation of perturbing electrostatic forces arising in passing from a particular molecule, or molecular conformation, to another one is applied. Using the existing experimental and ab initio calculation data the model capabilities are demonstrated for typical organic molecules consisting of Н, С, N, O, F, Si, S and Cl atoms.

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Abbreviations

ED:

electron density

EN:

electronegativity

ESF:

electrostatic force

S-ESF:

short-range ESF

M-ESF:

middle-range ESF

L-ESF:

long-range ESF

FM:

fixed molecule

IM:

idealized molecule

LED:

local electron density

LP:

lone pair of electrons

MEI direction:

direction of the most effective interaction

MW:

microwave spectroscopy

PPC:

point positive charge

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Authors and Affiliations

  1. Department of High Energy Chemistry, Mendeleev University of Chemical Technology, Moscow, 125047, Russia

    M. A. Kirpichenok & Z. Y. Titarenko

  2. ASINEX Ltd., Moscow, 125480, Russia

    N. A. Vasilevich

  3. Department of Chemistry and Technology of Biomedical Preparations, Mendeleev University of Chemical Technology, Moscow, 125047, Russia

    E. N. Ofitserov

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  1. M. A. Kirpichenok
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Kirpichenok, M.A., Titarenko, Z.Y., Vasilevich, N.A. et al. Electrostatic forces and geometry of organic molecules. Part I. Saturated molecules with tetrahedral fragments. Ref. J. Chem. 7, 23–63 (2017). https://doi.org/10.1134/S2079978017010034

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