Lecture

Strain and Stabilization of Organic Molecules

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In course

CH-431: Physical and computational organic chemistry

This course introduces modern computational electronic structure methods and their broad applications to organic chemistry. It also discusses physical organic concepts to illustrate the stability and reactivity of organic molecules. ...

Description

This lecture delves into the concepts of strain and stabilization in organic molecules, exploring how different substituents influence strain energies. It discusses the impact of steric crowding, branching interactions, and ring strain on the stability of organic compounds. The lecture also covers the role of hyperconjugation and conjugation in stabilizing hydrocarbon systems, providing insights into the balancing of chemical reactions to estimate strain energies accurately.

Instructor

Anne-Clémence Corminboeuf

Teaching & PhD PhD Students Liam Oliver Marsh, Pratham Pushparaj Deshmukh, Roel Christiaan M Raike, Thanapat Worakul, Osvaldo Hernandez Cuellar, Juliette Veronique Schleicher, Yannick Calvino Alonso, Sara Bassetta, Yuri Cho, Kelian Dietmar Marc Gaedecke, Guoyuan Liu Past EPFL PhD Students Fabrice Avaltroni, Daniel Filipe Jana, Stephan Niklaus Steinmann, Jérôme Florian Gonthier, Riccardo Petraglia, Antonio Prlj, Laurent Alexis Clément Vannay, Alberto Fabrizio, Kun-Han Lin, Boodsarin Sawatlon, Raimon Fabreg

Official source

Related concepts (31)

Prelog strain

In organic chemistry, transannular strain (also called Prelog strain after chemist Vladimir Prelog) is the unfavorable interactions of ring substituents on non-adjacent carbons. These interactions, called transannular interactions, arise from a lack of space in the interior of the ring, which forces substituents into conflict with one another. In medium-sized cycloalkanes, which have between 8 and 11 carbons constituting the ring, transannular strain can be a major source of the overall strain, especially in some conformations, to which there is also contribution from large-angle strain and Pitzer strain.

Strain (chemistry)

In chemistry, a molecule experiences strain when its chemical structure undergoes some stress which raises its internal energy in comparison to a strain-free reference compound. The internal energy of a molecule consists of all the energy stored within it. A strained molecule has an additional amount of internal energy which an unstrained molecule does not. This extra internal energy, or strain energy, can be likened to a compressed spring.

Conformational isomerism

In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a molecule that differ by rotation about single bonds can be referred to as different conformations, conformations that correspond to local minima on the potential energy surface are specifically called conformational isomers or conformers.

Substituent

In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (in organic chemistry and biochemistry, the terms substituent and functional group, as well as side chain and pendant group, are used almost interchangeably to describe those branches from the parent structure, though certain distinctions are made in polymer chemistry. In polymers, side chains extend from the backbone structure.

Organic compound

In chemistry, many authors consider an organic compound to be any chemical compound that contains carbon-hydrogen or carbon-carbon bonds, however, some authors consider an organic compound to be any chemical compound that contains carbon. The definition of "organic" versus "inorganic" varies from author to author, and is a topic of debate. For example, methane () is considered organic, but whether some other carbon-containing compounds are organic or inorganic varies from author to author, for example halides of carbon without carbon-hydrogen and carbon-carbon bonds (e.

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