Two polymorphs of the industrially important compound diiminoisoindoline occur in the amino tautomeric form as a conformational isomorph with a 1 : 1 mixture of the syn- and anti-isomers, and a conformational polymorph containing only the syn-isomer.
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Cobalt(III)-containing penta-dentate "helmet"-type phthalogens: synthesis, solid-state structures and their thermal and electrochemical characterization.
Dalton Trans
February 2024
Research Center for Materials, Architectures and Integration of Nano-membranes (MAIN) Research Group Organometallic Chemistry, Technische Universität Chemnitz Rosenbergstraße 6, 09126 Chemnitz, Germany.
Treatment of unsubstituted and substituted phthalonitrile (1a-d) with appropriate equivalents of sodium methoxide and ammonia afforded the corresponding 1,3-diiminoisoindolines (2a-d), which were converted to cobalt(III)-containing penta-dentate "helmet"-type phthalogens (3a-d) by the reaction with CoCl·6HO as templating agent in the inert solvent 1,2,4-trichlorobenzene. The identities of 2a-d and 3a-d were established by elemental analysis, infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and electrospray ionization mass spectrometry (ESI-MS). A computational study was performed to determine the most stable tautomeric form of 2a-c in the gas phase.
View Article and Find Full Text PDFRational Synthesis of 5,10-Diazaporphyrins via Nucleophilic Substitution Reactions of α,α'-Dibromotripyrrin and Dihydrogenation to Give 5,10-Diazachlorins.
J Org Chem
March 2020
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
We report here the first rational synthesis of 5,10-diazaporphyrins via nucleophilic substitution reactions of α,α'-dibromotripyrrin. Uses of 1,3-diiminoisoindoline and 3,4-di(ethylsulfanyl)pyrrole-2,5-diimine as nucleophiles allowed for synthesis of 5,10-diazabenzoporphyrin () and 5,10-diaza-7,8-di(ethylsulfanyl)porphyrin (3). 3 was reduced to 5,10-diazaporphyrin (), 5,10-diaza-2,3-dihydrogenated porphyrin (), and 5,10-diaza-7,8-dihydrogenated porphyrin () with yields that were dependent upon reduction conditions.
View Article and Find Full Text PDFDiiminoisoindoline: tautomerism, conformations, and polymorphism.
Chem Commun (Camb)
April 2004
Center for Advanced Materials, Department of Chemistry, University of Massachusetts Lowell, Lowell, Massachusetts 01854-5046, USA.
Two polymorphs of the industrially important compound diiminoisoindoline occur in the amino tautomeric form as a conformational isomorph with a 1 : 1 mixture of the syn- and anti-isomers, and a conformational polymorph containing only the syn-isomer.
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