Host–guest chemistry. Methanol, ethanol and propan‐1‐ol inclusion compounds of 2‐[o‐(triphenylphosphoranylidenamino) benzyliden] amino‐1H‐2, 3‐dihydroindazol‐3‐one. X‐ray structural characterization of the free host and its ethanol inclusion compound
- 1 August 1992
- journal article
- research article
- Published by Wiley in Journal of Physical Organic Chemistry
- Vol. 5 (8) , 507-517
- https://doi.org/10.1002/poc.610050813
Abstract
The title compound (3) which is a 2‐aminoindazol‐3‐one derivative linked through a methinephenyl bridge to an iminophosphorane, and unrelated to any previous host, is described. The bulky triphenylphosphino group provides the cavity and the indazol‐3‐one the hydrogen bonds (both donor NH and acceptor CO). X‐ray structural analyses of the free host 3 and that of its ethanol inclusion compound 3 · EtOH are reported. Hydrogen bonds resulting in infinite chains dominate the molecular packing. The use of thermal analysis and 13C CP/MAS NMR shed light in the structures of two other inclusion compounds, 3 · MeOH and 3 PrOH. The conclusion is that all three compounds are similar. An analysis of the cavities, using a model of interpenetrating spheres of van der Waals radii, demonstrates that in the case of the ethanol derivative, the cavity has the space and form requirements necessary to include the propanol guest.Keywords
This publication has 15 references indexed in Scilit:
- Iminophosphorane-substituted proton sponges. Part 1. X-ray molecular structures of 1,8-diaminonaphthalene and 1-amino-8-triphenylphosphoranylideneaminonaphthaleneJournal of the Chemical Society, Perkin Transactions 2, 1991
- Heterocycles by intramolecular aza-Wittig reactions of iminophosphoranes obtained from 2-azidobenzoyl- and 2-azidobenzylidene derivativesTetrahedron Letters, 1990
- SIR88 – a direct-methods program for the automatic solution of crystal structuresJournal of Applied Crystallography, 1989
- Experimental and theoretical study of the R3P+-X- bond. Case of betaines derived from N-iminophosphoranes and alkyl isocyanatesJournal of the American Chemical Society, 1989
- Host-guest compounds. x-ray structure, differential scanning calorimetry, and thermogravimetry of methanol, ethanol, isopropanol, tert-butanol and dioxame Inclusion compounds in 7-benzoyl-6-phenyl-6,7-dihydro-1-methyl-3-methylthio-5-1.2,4-triazolo[3.4-][1,3,4]thiadiazinium bromideTetrahedron, 1988
- Synthesis of 6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines by a C–C ring cyclization under mild conditionsJournal of the Chemical Society, Perkin Transactions 1, 1987
- The structure of indazolinone and derivatives in the solid state and in solution: an X-ray and nuclear magnetic resonance studyJournal of the Chemical Society, Perkin Transactions 2, 1986
- Systematic analysis of structural data as a research technique in organic chemistryAccounts of Chemical Research, 1983
- An empirical method for correcting diffractometer data for absorption effectsActa Crystallographica Section A Foundations of Crystallography, 1983
- The crystal and molecular structure of 2-acetyl-3-indazolinone, C9H8N2O2Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1969