23303-09-5

Basic information

• Product Name: pyrrolide anion
• Synonyms: pyrrolide anion
• CAS NO: 23303-09-5
• Molecular Weight: 66.0825
• Mol File: 23303-09-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: pyrrolide anion(CAS DataBase Reference)
• NIST Chemistry Reference: pyrrolide anion(23303-09-5)
• EPA Substance Registry System: pyrrolide anion(23303-09-5)

Safety Data

• Hazardous Substances Data: 23303-09-5(Hazardous Substances Data)

Upstream product

• 109-97-7 pyrrole 
• 70019-89-5 4-Methylimidazolate anion 
• 14213-96-8 C₄H₄N^(1-)*C₂H₃N 

Downstream Products

• 109-97-7 pyrrole 
• 41458-22-4 2-Aminopyridin 
• 77354-32-6 N-methylacetamide anion 
• 58272-35-8 C₂H₄NO^(1-) 
• 2051-97-0 1-benzyl-1H-pyrrole 
• 67131-48-0 formamide; deprotonated form 

Relevant articles and documents

The Ionic Hydrogen Bond and Ion Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules

The bonding energy of a water molecule to carbanions range from 11.0 kcal/mol for c-C5H5- to 13 - 15 kcal/mol for CH2CN-, CH2CHO-, and CH2COCH3- and to 16.2 kcal/mol for HCC-.Alcohols bond to c-C5H5- more strongly, by up to 20.6 kcal/mol for the strongly acidic CF3CH2OH, and the attachment energies show an inverse linear correlation with the acidities of the alcohols.The c-C5H5- ion exhibits unusual behavior in that it bonds to the hydrogen donor H2O more weakly (11.0 kcal/mol) than to CH3CN (15.5 kcal/mol).In contrast, the more localized pyrrolide ion c-C4H4N- bonds to the two solvents by comparable strength, 15.8 and 15.7 kcal/mol, respectively.These observations indicate a specific N-*OH hydrogen bonding contribution in c-C4H4N-*H2O, and/or an unusual C-*HC type hydrogen bonding contribution in c-C5H5-*CH3CN.As to structures, correlations between ΔHoD and ΔHoacid suggest that ligands may hydrogen bond to the ? system of c-C5H5-, and to the oxygen atoms in CH2CHO- and CH3COCH2-.The latter is supported by solvent shell effects in CH3COCH2-*nH2O.