Co-crystallization of pentacyclododecane acetate rotamers of opposite chirality: effects of steric interactions and negative hyperconjugation on molecular structure

Seidl, Peter Rudolf; Sabino, José R.; Castellano, Eduardo E.; Mascarenhas, Yvonne P.; Costa, Valentim Emı́lio Uberti; Alifantes, João; Silva, Carlos Henrique Tomich de Paula da; Dias, Jacques F.

doi:10.1016/s0022-2860(03)00204-7

Cited by 2 publications

(1 citation statement)

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“…Results indicate that, in all molecular models studied, a bond path is found to exist between the congested atoms. At equilibrium, that is, for the energy minimized molecular structures, the congested atoms are found to be separated by a distance well below the sum of the van der Waals radii, an observation also confirmed by a number of available experimental structures of some of the molecules shown in Scheme and similar compounds found in the literature …”

Section: Discussionsupporting

confidence: 74%

Congested molecules. Where is the steric repulsion? An analysis of the electron density by the method of interacting quantum atoms

Dillen

2013

Int J of Quantum Chemistry

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The computed electron density of several congested saturated hydrocarbons and halogenated derivatives has been analyzed by the method of interacting quantum atoms (IQA). For all the molecules studied, the calculations show the existence of a bond path between the congested atoms and which, according to the Quantum Theory of Atoms in Molecules, indicates that there is a stabilizing interaction between these atoms. The bond path is found to exist up to interatomic distances well-beyond the sum of the van der Waals radii. The IQA results indicate that steric hindrance is not a repulsive force between the congested atoms but that is the result of an increase in the intra-atomic or self-energy of the congested atoms. This increase in self-energy is caused by the deformation of the atomic basin of the congested atoms.

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Section: Discussionsupporting

confidence: 74%