Potassium 3-oxo-2,3-dihydro-1H-inden-4-olate: Formation, molecular and electronic structure

Sigalov, M. V.; Shainyan, B. А.; Sterkhova, Irina V.

doi:10.1016/j.molstruc.2016.06.023

Cited by 2 publications

(2 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An attempt to synthesize compound 3 from 7-hydroxy-1-indanone 1 under the conditions of basic catalysis similar to those used by us earlier failed. In the presence of KOH, compound 1 did not enter the reaction of condensation with 1 H -pyrrole-2-carbaldehyde but, instead, gives the salt, potassium 3-oxo-2,3-dihydro-1 H -inden-4-olate . Therefore, target compound 3 was obtained from 7-methoxy-1-indanone by condensation with 1 H -pyrrole-2-carbaldehyde under basic conditions giving the model compound 7 with subsequent removal of the protecting methyl group by the reaction with BBr 3 .…”

Section: Synthesismentioning

confidence: 99%

“…In the presence of KOH, compound 1 did not enter the reaction of condensation with 1H-pyrrole-2-carbaldehyde but, instead, gives the salt, potassium 3-oxo-2,3-dihydro-1H-inden-4-olate. 19 Therefore, target compound 3 was obtained from 7-methoxy-1-indanone by condensation with 1H-pyrrole-2-carbaldehyde under basic conditions giving the model compound 7 with subsequent removal of the protecting methyl group by the reaction with BBr 3 . 20 Compounds 4−6 were synthesized by acid-catalyzed aldol condensation of 1 with 4-dimethylaminophenylbenzaldehyde, 4-nitrophenylbenzaldehyde, or glyoxylic acid, respectively.…”

Section: ■ Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Photoinduced Intramolecular Bifurcate Hydrogen Bond: Unusual Mutual Influence of the Components

2017

View full text Add to dashboard Cite

A series of 7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-ones with 2-pyrrolyl (3), 4-dimethylaminophenyl (4), 4-nitrophenyl (5), and carboxyl group (6) as substituents at the exocyclic double bond was synthesized in the form of the E-isomers (4-6) or predominantly as the Z-isomer (3) which in solution is converted to the E-isomer. The synthesized compounds and their model analogues were studied by NMR spectroscopy, X-ray analysis, and MP2 theoretical calculations. The E-isomers having intramolecular O-H···O═C hydrogen bond are converted by UV irradiation to the Z-isomers having bifurcated O-H···O···H-X hydrogen bond. Unexpected shortening (and, thus, strengthening) of the O-H···O═C component of the bifurcated hydrogen bond upon the formation of the C═O···H-X hydrogen bond was found experimentally, proved theoretically (MP2), and explained by a roundabout interaction of the H-donor (HX) and H-acceptor (C═O) via the system of conjugated bonds.

show abstract

Section: Synthesismentioning

confidence: 99%

Section: ■ Synthesismentioning

confidence: 99%

Photoinduced Intramolecular Bifurcate Hydrogen Bond: Unusual Mutual Influence of the Components

2017

View full text Add to dashboard Cite

show abstract

Hydrogen bonding-assisted transformations of cyclic chalcones: <i>E/Z</i>-isomerization, self-association and unusual tautomerism

Shainyan¹,

Sigalov²

2022

Usp. khim.

View full text Add to dashboard Cite

Condensation of 1- or 2-indanones and 1,3-indandiones with aromatic or heteroaromatic carbaldehydes gives products that demonstrate various transformations and effects of general interest for organic chemistry. In the present review, phenomena such as tautomerism, E/Z-isomerization, π-conjugation, hydrogen bonding, and homo- and heteroassociation are considered. The relative stability of various isomers of cyclic chalcones is shown to be determined by the intramolecular hydrogen bonding in their molecules and the formation of associates. The same effects also result in the formation of unusual, otherwise unstable tautomers, such as 2H-indazoles. The hydrogen bonding-assisted keto-enol and E/Z-isomerization are analyzed. A novel, specific type of conjugation for the studied compounds was proposed and termed "roundabout" conjugation. The bibliography includes 101 references.

show abstract

Potassium 3-oxo-2,3-dihydro-1H-inden-4-olate: Formation, molecular and electronic structure

Cited by 2 publications

References 16 publications

Photoinduced Intramolecular Bifurcate Hydrogen Bond: Unusual Mutual Influence of the Components

Photoinduced Intramolecular Bifurcate Hydrogen Bond: Unusual Mutual Influence of the Components

Hydrogen bonding-assisted transformations of cyclic chalcones: <i>E/Z</i>-isomerization, self-association and unusual tautomerism

Contact Info

Product

Resources

About