Intramolecular and intermolecular bifurcated hydrogen bonds in 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one

Nina N. Chipanina; Larisa P. Oznobikhina; Mark V. Sigalov; Bagrat A. Shainyan

doi:10.1002/poc.3924

Intramolecular and intermolecular bifurcated hydrogen bonds in 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one

Nina N. Chipanina, Larisa P. Oznobikhina, Mark V. Sigalov, Bagrat A. Shainyan

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Cyclic and linear dimers as well as the solvate H-bonded complexes of the Z and E isomers of 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one 1 were investigated by theoretical calculations, and their formation was proved by FT-IR and UV spectroscopy. In dimers, both strengthening and weakening of the intramolecular component of the bifurcated hydrogen bond are observed depending on the type of the formed intermolecular hydrogen bond. The effect of proton donors MeOH, HCN, and proton acceptor DMSO on the intramolecular components in solvent H-bonded complexes is discussed. A larger energy gap in the 1-E than in 1-Z isomer allows to predict photoinduced isomeric transition 1-Е → 1-Z in nonpolar aprotic solvents.

Original language	English
Article number	e3924
Journal	Journal of Physical Organic Chemistry
Volume	32
Issue number	4
DOIs	https://doi.org/10.1002/poc.3924
State	Published - 1 Apr 2019

Keywords

bifurcation
hydrogen bonds

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/poc.3924

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title = "Intramolecular and intermolecular bifurcated hydrogen bonds in 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one",

abstract = "Cyclic and linear dimers as well as the solvate H-bonded complexes of the Z and E isomers of 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one 1 were investigated by theoretical calculations, and their formation was proved by FT-IR and UV spectroscopy. In dimers, both strengthening and weakening of the intramolecular component of the bifurcated hydrogen bond are observed depending on the type of the formed intermolecular hydrogen bond. The effect of proton donors MeOH, HCN, and proton acceptor DMSO on the intramolecular components in solvent H-bonded complexes is discussed. A larger energy gap in the 1-E than in 1-Z isomer allows to predict photoinduced isomeric transition 1-Е → 1-Z in nonpolar aprotic solvents.",

keywords = "bifurcation, hydrogen bonds",

author = "Chipanina, {Nina N.} and Oznobikhina, {Larisa P.} and Sigalov, {Mark V.} and Shainyan, {Bagrat A.}",

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T1 - Intramolecular and intermolecular bifurcated hydrogen bonds in 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one

AU - Chipanina, Nina N.

AU - Oznobikhina, Larisa P.

AU - Sigalov, Mark V.

AU - Shainyan, Bagrat A.

PY - 2019/4/1

Y1 - 2019/4/1

N2 - Cyclic and linear dimers as well as the solvate H-bonded complexes of the Z and E isomers of 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one 1 were investigated by theoretical calculations, and their formation was proved by FT-IR and UV spectroscopy. In dimers, both strengthening and weakening of the intramolecular component of the bifurcated hydrogen bond are observed depending on the type of the formed intermolecular hydrogen bond. The effect of proton donors MeOH, HCN, and proton acceptor DMSO on the intramolecular components in solvent H-bonded complexes is discussed. A larger energy gap in the 1-E than in 1-Z isomer allows to predict photoinduced isomeric transition 1-Е → 1-Z in nonpolar aprotic solvents.

AB - Cyclic and linear dimers as well as the solvate H-bonded complexes of the Z and E isomers of 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one 1 were investigated by theoretical calculations, and their formation was proved by FT-IR and UV spectroscopy. In dimers, both strengthening and weakening of the intramolecular component of the bifurcated hydrogen bond are observed depending on the type of the formed intermolecular hydrogen bond. The effect of proton donors MeOH, HCN, and proton acceptor DMSO on the intramolecular components in solvent H-bonded complexes is discussed. A larger energy gap in the 1-E than in 1-Z isomer allows to predict photoinduced isomeric transition 1-Е → 1-Z in nonpolar aprotic solvents.

KW - bifurcation

KW - hydrogen bonds

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DO - 10.1002/poc.3924

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JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

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ER -

Intramolecular and intermolecular bifurcated hydrogen bonds in 2-pyrrolyl-7-hydroxy-2-methylidene-2,3-dihydro-1H-inden-1-one

Abstract

Keywords

ASJC Scopus subject areas

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