Electrophilic aromatic substitution in cyclopropenium ions

Journal Article · Fri May 09 00:00:00 EDT 1980 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01298a010· OSTI ID:5130186

Clark, T; Weiss, R

Electrophilic attack by a proton on the cyclopropenium ion is shown by ab initio molecular orbital theory to involve a planar tetracoordinate carbon atom. The process is, however, strongly endothermic, and the protonated cyclopropenium ion ring opens without activation energy. The diaminocyclopropenium ion, on the other hand, can be either C or N protonated exothermically. C protonation can account for the observed H/D exchange in derivatives of the diaminocyclopropenium ion. In this case the protonated ion has a normal tetrahedral carbon atom and is highly stabilized by charge delocalization to nitrogen.

• Research Organization: Erlangen-Nuernberg Univ., Germany
• OSTI ID: 5130186
• Journal Information: J. Org. Chem.; (United States), Vol. 45:10
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
DEUTERIUM
ISOTOPIC EXCHANGE
CYCLOALKANES
EXPERIMENTAL DATA
ALKANES
DATA
HYDROCARBONS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPES
LIGHT NUCLEI
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
STABLE ISOTOPES
400303* - Organic Chemistry- Isotope Exchange & Isotope Separation- (-1987)