Strongly Polarized Carbon: Taming Fundamental Intermediates and Their Applications

Introduction

In CC-CHARGED, I propose a new concept to induce CC bond polarization as well as predict fundamentally new stable carbon-based compound classes. The manipulation of functional groups builds the basis for the rational design of complex molecules in organic synthesis.

Exploration of Compound Classes

While most compound classes have been studied for decades, few remain virtually unexplored, only suggested as reactive intermediates. I propose to tame these elusive intermediates into hitherto unknown room-temperature stable compound classes.

Polarization Mechanism

The central motif to gain stability relies on the polarization of the CC bond, which can either result in zwitterions (charged +/-) or diradicals. The dichotomic behavior will be analyzed, and a general approach to CC bond polarization will be developed based on a new concept of mesoionic frustration.

Mesoionic Frustration

Such mesoions are predicted to be exceptionally strong polarized carbon compounds, exceeding the polarization of traditional ylides. This polarization triggers applications from transition metal, main group chemistry to organic synthesis.

Reactivity Analysis

The reactivity of such strong carbon donors will be analyzed, correlated, and a scale generated. Applications of CC bond polarization in the stabilization of unsaturated diazo and monosubstituted carbon compounds are presented. Their synthesis, electronic structure, and reactivity will be evaluated, and applications such as C-atom transfer reagents for molecular editing studied.

Vinylidene Compounds

While singlet vinylidenes are central intermediates in organic reactions, the generation and reactivity of triplet vinylidenes is virtually unknown. I propose them as new compounds in organic chemistry, as metal-vinylidene precursors, and as new platforms for magnetic applications.

Foundation of the Project

Recent high-impact publications by the group build the basis for this project that goes far beyond the state-of-the-art. Considering that carbon is the pivotal element of life and the central element of organic chemistry, CC-CHARGED is a fundamental, ground-breaking contribution to organic chemistry.