72738-57-9

Basic information

• Product Name: trans-N,N'-dibenzoylindigo
• Synonyms: trans-N,N'-dibenzoylindigo
• CAS NO: 72738-57-9
• Molecular Weight: 470.484
• Mol File: 72738-57-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: trans-N,N'-dibenzoylindigo(CAS DataBase Reference)
• NIST Chemistry Reference: trans-N,N'-dibenzoylindigo(72738-57-9)
• EPA Substance Registry System: trans-N,N'-dibenzoylindigo(72738-57-9)

Safety Data

• Hazardous Substances Data: 72738-57-9(Hazardous Substances Data)

Upstream product

• 72738-54-6 cis-N,N'-dibenzoylindigo 
• 98-88-4 benzoyl chloride 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 

Downstream Products

• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 54778-23-3 2-(2-benzamidophenyl)-2-oxoacetic acid 
• 72738-54-6 cis-N,N'-dibenzoylindigo 
• 860418-76-4 1-benzoyl-12'-chloro-spiro[indoline-2,11'-indolo[1,2-b]isoquinoline]-3,6'-dione 

Relevant articles and documents

Liquid-Crystalline Solvents as Mechanistic Probes. 17. Influence of Cholesteric and Smectic Mesophase Order on the Isomerization of Some N,N'-Diacylindigos

The rates and activation parameters for cis -> trans thermal isomerization of four N,N'-diacylindigos have been compared in isotropic and liquid-crystalline phases.The results indicate that cholesteric solvent order has no perceptable influence on the isomerization of N,N'-diacetylindigo.The shape changes attendant upon isomerization of N,N'-diacylindigos are inhibited by smectic phase order when the acyl chains are incorporated into smectic layers: the indigoid portion of the molecule, per se, does not sense on a microscopic level the macroscopic order of the smectic phase.Thus, the activation parameters for isomerization of cis-N-acetyl-N'-stearoylindigo and cis-N,N'-distearoylindigo in the isotropic phase of n-butyl stearate (BS) are within experimental error of each other and are similar to the values obtained when benzene is solvent; in the smectic B phase of BS, the activation enthalpy and activation entropy of N,N'-distearoylindigo are, respectively, 7 kcal/mol larger and 18 eu more positive than the values of N-acetyl-N'-stearoylindigo.

The Thermal Cis-to-trans Isomerization of N,N'-Diacylindigos. Kinetic Pressure, Solvent, and Substituent Effects.

The kinetics of the thermal cis-to-trans isomerization of N,N'-diacylindigos(DAI) in various solvents and under high pressures has been studied.N,N'-Dibenzoylindigos(DBI) isomerize about 10 times slower than molecules not having a benzene ring in the acyl groups.The values of the activation volumes were about 8.0 cm3 mol-1 for the former and about 3.0 cm3 mol-1 for the latter.It was suggested that the thermal isomerization proceeds via the biradical mechanism.The positive values of the activation volume have been interpreted in terms of the increase in theintrinsic volume upon activation.The differences in the isomerization rates and the activation parameters between DBI and the others have been ascribed to an additional interaction between the two phenyl rings in the acyl groups in the cis-ground state.