Welcome to the Gold Lab at UNM
Understanding bioorganic structure and reactivity for the precise control of molecular properties and transformations

Stereoelectronic Effects

Electronic stabilization maximized by a particular geometric arrangement of orbitals in space.

Stereoelectronic effects

Molecules adopt geometries to facilitate effective delocalization—the basis of stereoelectronic effects. Functional groups with high-energy filled orbitals align themselves to communicate with those bearing low-energy unfilled orbitals. Furthering our understanding of stereoelectronic interactions within living systems will provide a framework for the development of improved therapeutics, materials, and processes.

In addition to our interest in the stereoelectronic control of bioorthogonal 1,3-dipolar cycloadditions, we are interested in elucidating interactions that control reactivity in living systems. We have recently revealed n➝π* interactions acting as oxyanion holes in aspartic proteases—providing substrate-assistance to proteolysis. These insights further our understanding of biochemical reactivity and provide new targets for drug design.


See also:

Alabugin, I. V.; Gold, B. Stereoelectronic Effects: Origins and Consequences on Structure and Reactivity of Organic Molecules. in: Wang, Z. Encyclopedia of Physical Organic Chemistry; Wiley: Chichester, 2017.

Alabugin, I.V. Stereoelectronic Effects: A Bridge Between Structure and Reactivity. Wiley: Chichester, 2016.

More coming soon…